CIOs and CISOs have many strategic and operational fears when it comes to unleashing fully-autonomous agents on tasks and hoping that everything works out. Will the agent start to delete critical files? Will the agent go off on a mission tangent and generate a massive token bill for the team when they return the next morning? Will it be tricked by a state actor and engage in malicious actions?

To help alleviate those concerns, OpenAI announced on Thursday that it has agreed to acquire Ona, a 79 person cloud development environment (CDE) provider formerly known as Gitpod, to accelerate its efforts to make agentic AI enterprise-friendly. 

An OpenAI statement said Ona’s technology “provides secure, persistent environments where agents can access the tools, systems, and context they need to make progress over time. By bringing Ona to OpenAI, we will expand Codex beyond work tied to a single device or active session and help more organizations deploy agents securely in production.”

An Ona statement attributed to CEO Johannes Landgraf shared similar sentiments.

“Ona brings the building blocks agents need for enterprise work: trusted, customer-controlled cloud environments where work continues across devices, inside the systems where software actually lives,” Landgraf said. “OpenAI brings frontier intelligence, product polish, and a scale of research and distribution we could never reach alone.”

Landgraf’s statement did not provide any annual revenue numbers, but did hint, without naming, at some large customers. “Since the beginning of the year, weekly Ona agent sessions have grown 13x in production across some of the world’s most demanding institutions: the oldest bank in the US, one of Europe’s largest pharma companies, one of Asia’s largest sovereign wealth funds and many others,” he wrote. “The largest enterprises out there love the platform and are expanding more rapidly than ever before.”

Arnal Dayaratna, research VP for software development at IDC, said IDC’s figures for Ona put its annual revenue for 2025 at “roughly $7 million.” He speculated that Ona’s revenue for 2026 would be higher: “Let’s say it’s $15 million. I am being generous. Maybe it’s really $10 million or $12 million.”

Dayaratna said if he uses a standard acquisition price of roughly a multiple of 30 times revenue, then depending on the actual 2026 figure, “that comes to $450 million or $500 million or so.”

But IDC sees this being a potentially good move for OpenAI, regardless of the specific acquisition price, given that OpenAI had the classic “buy or build” challenge. 

OpenAI has a substantial Codex effort, Dayaratna said, but what they lack is a safe area to protect enterprise autonomous agent efforts. “This is outside of what OpenAI has now. These are secure environments where agents can have memory and operate securely,” he said. “This is the kind of technology that one would expect to be needed, but I don’t know how good it is, to be honest.”

Gartner’s First Take, published today, noted that the acquisition will bring Codex “the essential scaling capability it lacked,” but also pointed out it forces some difficult decisions on enterprises: “Software engineering leaders must weigh the benefits of a vendor-specific integrated stack against the flexibility of staying vendor-agnostic.”

In addition, Gartner wrote, “This acquisition appears to be OpenAI’s response to Anthropic supporting self-hosted sandboxes in Claude Managed Agents, starting May 2026.”

Tom Findling, CEO of Conifers.ai, said he also sees OpenAI’s fear of Anthropic playing a meaningful role in this deal. 

“It feels like a move to keep pressure on Anthropic, especially as Claude Code gains traction with developers and enterprise buyers,” he said. “So I’d read this less as OpenAI taking out a small competitor and more as OpenAI trying to make sure Codex is enterprise-ready before Anthropic gets too far ahead. In the enterprise market, the battle is not just who has the smartest coding model, but who can make AI agents safe and useful enough for big companies to actually deploy.”

He added, “I don’t think this means OpenAI suddenly needs help making Codex better at writing code. The bigger issue is making Codex work inside real enterprise environments, where security, access controls, persistent cloud workspaces, audit trails, and integration with existing developer workflows matter just as much as the model itself. Ona gives OpenAI some of that missing plumbing.”

Jason Andersen, principal analyst for Moor Insights & Strategy, echoed the concerns about Anthropic.

“To be honest, I think it reinforces what I think, which is that OpenAI and Codex have given a lot of ground to Anthropic and Claude Code, who are winning right now,” he said. “But again, this is not about the market today, I think it’s about how OpenAI will need to position itself as more than just a model as we see the incumbent players, particularly Microsoft, bolster their enterprise coding infrastructure story.”

Andersen said that Moor doesn’t have any strong basis for a guess on the financials, but added, “I am going to assume it was a fairly high multiple, but on a small base. I would not speculate on an amount, but given the enterprise customers that Ona did have, it may be more than we think.”

He also reinforced the idea that OpenAI is going to need help to achieve its own objectives.

“We continue to see that AI adoption is strongest in coding, and other use cases are not as far along,” he said. “So, if you are a general-purpose AI company like OpenAI, you need to double down on development use cases. The meaningful investment and spending on development is happening at the enterprise level, and those customers have more demands for governance, security, etc. than Codex or Claude code can handle.”

That said, he noted, “what you’re seeing is traditional software and cloud plays building out the coding and ops infrastructure around the popular models. That increased competition, while good for selling tokens, is still keeping OpenAI and Anthropic on the outside looking in. So, OpenAI and Anthropic need a stronger enterprise dev story, or they are just another model that could be easily replaced.”

Jeremy Roberts, senior director at Info-Tech Research Group, said that he also sees this as likely a good move for OpenAI.

“OpenAI is growing up a little bit,” and they may be falling behind Anthropic, Roberts said. “I see Ona as a boring company, but not in a bad way. They are not flashy, but absolutely necessary.”

Ona is delivering a workspace for Codex that an enterprise can run in its own virtual private cloud, with governance and persistence and an environment where the company can apply their own controls including log management, credential management and resource access, he said. “It is a bucket for the agents to operate in” where IT can “make sure that access is properly credentialed and is controlled effectively to prevent the model doing what it shouldn’t be doing,” which includes managing read/write protections.

When Pope Leo XIV wrote about the effect that AI is having on our world in his encyclical, Magnifica Humanitas, he may not have imagined the document being referenced in an HR environment.

But, according to a report by Business Insider, Erin Maus, a software developer in North Carolina, used the Pope’s message about the need for vigilance in how AI would be deployed to gain a special exemption from her employer about using the technology for coding.

Maus is not even a Catholic but a Unitarian Universalist, according to the report. However, it said, she maintained that the use of AI didn’t align with her religious beliefs.

Business Insider said that to make her case, she consulted an employment lawyer — a move to be expected — and her local chapter’s minister — which probably wasn’t. Her wishes were reportedly granted last month. “I’m writing my code and reviewing my code by hand, which seems crazy to say,” she told the publication.

She’s certainly not alone in wondering whether AI is always the way forward for techies: a journalist at PC World has also been rethinking its use after reading the encyclical.

It remains to be seen whether this will be the spur for a torrent of claims from Catholic workers, asking to be freed from the demands of using AI or whether Business Insider’s report is an outlier.

Microsoft has open-sourced an AI evaluation framework that converts natural-language requirements into executable tests, expanding its push into enterprise AI governance as organizations struggle to validate agent behavior before production deployments systematically.

The framework, called ASSERT (Adaptive Spec-driven Scoring for Evaluation and Regression Testing), generates evaluation scenarios, datasets, metrics, and scorecards from written specifications, product requirements, and governance documents, Microsoft said in a blog post announcing the release.

“Agents fail in ways that are hard to see,” Microsoft wrote in the blog post. “They drift from policy, produce unsafe outputs in edge cases, and behave differently in production than they did in testing. Generic benchmarks do not catch these failures because they are not built around your policies, your agent, or your use case.”

Rather than requiring developers to manually create evaluation suites, ASSERT translates written intent into reusable tests that can be integrated into AI development pipelines, the company said in the blog post.

With ASSERT, Microsoft is entering an increasingly competitive AI evaluation market that already includes platforms such as LangChain’s LangSmith, Braintrust, Patronus AI, Galileo, Arize AI’s Phoenix, and Promptfoo, which help enterprises benchmark, monitor, and validate large language model applications.

Behavioral testing remains immature

The release comes as enterprises rapidly expand AI agent deployments while formal evaluation practices remain the exception rather than the rule.

“Most organizations, in fact, 99% of them, do not evaluate any AI agents pre-production,” said Anushree Verma, senior director analyst at Gartner.

According to Verma, the industry’s next competitive advantage will depend less on advances in reasoning models than on how effectively organizations simulate and stress-test AI agents before deployment.

“The next competitive moat in agentic AI is not about the sophistication of reasoning models or the underlying architecture,” she said. “It will be about the depth and realism of the training environment through agentic simulation, particularly for mission-critical deployments.”

Gartner estimates that by 2029, more than 75% of domain-specific agents designed without agentic simulation in regulated industries will fail to deliver value.

Forrester sees enterprises moving toward behavioral evaluation but says most organizations have yet to make it a formal production requirement.

“Most enterprises are still in an intermediate stage where behavioral evaluation is inconsistently applied rather than treated as a formal production gate,” said Biswajeet Mahapatra, principal analyst at Forrester.

According to Forrester data, more than 45% of organizations are already using AI agents, and another 25% are piloting them, yet many continue to struggle with scaling because of immature governance and limited operational rigor.

“The net is that behavioral evaluation is becoming important, but for most organizations it is still ad hoc or tool-driven rather than a standardized release gate enforced across the lifecycle,” Mahapatra said.

AI judges still need human oversight

Microsoft said ASSERT uses large language models as judges, with model-generated evaluations agreeing with human reviewers 80% to 90% of the time in the company’s internal validation.

That level of agreement can help automate large portions of AI testing, but should not be treated as a standalone governance mechanism, Mahapatra said.

“An 80% to 90% agreement rate with human reviewers indicates strong alignment but is not sufficient as a standalone control for governance or compliance,” he said.

Instead, enterprises should adopt layered oversight where AI evaluates AI at scale while humans retain supervisory accountability for high-risk, regulated, or ambiguous scenarios. Buyers should also watch for bias, consistency issues, and overreliance on a single model acting as both generator and evaluator, he added.

Open source reduces lock-in, not governance risk

Microsoft released ASSERT under the MIT open-source license, allowing organizations to inspect, modify, and integrate the framework into existing AI development workflows.

But open sourcing a framework does not eliminate questions around evaluation neutrality, Mahapatra said.

“Open sourcing under an MIT license reduces lock-in concerns and enables broad interoperability across model ecosystems,” he said. “However, it does not fully eliminate trust or conflict-of-interest questions because the originating vendor still influences how evaluation criteria, scoring logic, and definitions of acceptable behaviour are encoded.”

Instead of relying on a single evaluation framework, enterprises should validate AI systems against multiple evaluation approaches and retain ownership of internal evaluation policies, he said.

Between 2029 and 2032, every currently supported long-term support (LTS) version of Java will reach end-of-support within a single three-year window: Java 17 in 2029, Java 8 in 2030, Java 21 in 2031, and Java 11 in 2032.

On paper, this looks like a manageable upgrade cycle. In practice, it creates a collision of timelines that most enterprises have failed to forecast. Organizations attempting to modernize incrementally—moving application by application, version by version—are operating on a model that the calendar has already rendered obsolete.

The primary danger here is the illusion of time. Traditional modernization plans rely on sequential upgrades and controlled pacing. However, when every major Java version expires in the same compressed window, sequential planning collapses. By the time this becomes obvious, organizations will be forced into reactive mode, making rushed decisions under extreme pressure.

The modernization illusion

For organizations planning traditional stepwise upgrades—Java 8 to Java 11 to Java 17 to Java 21—this convergence elevates a routine maintenance task into a structural crisis. Enterprises with large Java estates will be forced to upgrade multiple applications across multiple versions simultaneously to maintain security compliance and business continuity. Waiting until the late 2020s to act guarantees a modernization process under emergency conditions.

While modern Java versions maintain strong backward compatibility, they cannot offset the drag of what enterprises are carrying forward: decades of accumulated technical debt.

In large Java environments, technical debt is pervasive. It exists as unused libraries, obsolete logic, forgotten dependencies, and dormant features—quietly inflating the size, risk, and complexity of every modernization effort. In many organizations, a significant portion of the codebase no longer executes in production, yet it still consumes developer attention, security oversight, and planning effort.

As codebases grow older and larger, this drag compounds. What looks like a simple version upgrade on a roadmap becomes a massive operational burden in practice.

Why incremental planning fails

Most modernization strategies assume that upgrades can be sequenced and absorbed gradually. That assumption is now dangerous. When multiple Java versions reach end-of-support in the same narrow window, enterprises don’t face a single modernization project—they face parallel modernization across their entire estate.

This shifts the challenge from engineering complexity to organizational capacity.

Consider a typical enterprise with 100 developers. If even a fraction of their time is spent maintaining, investigating, or working around unused and obsolete code, the organization burns meaningful engineering capacity on work that delivers no business value. Multiply that across dozens or hundreds of applications, and the bottleneck becomes clear: modernization is limited by people, not frameworks.

Parallel modernization requires parallel capacity—something most organizations haven’t budgeted for.

This explains why traditional approaches struggle to scale. Tools that analyze code in isolation cannot distinguish what actually matters in production. Without clear visibility into what code is relevant, organizations default to caution, effectively converting their timelines into risk.

The real bottleneck: developer capacity

The Java modernization crunch is a crisis of resource allocation, not a technology problem.

Every hour developers spend maintaining obsolete code or investigating unused dependencies is an hour lost to modernization. When organizations face simultaneous upgrades across multiple applications, human capacity becomes the limiting factor. Sequential planning and parallel modernization require the time and capacity most enterprises no longer have.

Organizations that delay action are consuming their flexibility rather than preserving it. Each year of inaction increases the volume of code that must be moved, reviewed, secured, and modernized within the same fixed window. By the time deadlines become unavoidable, the only remaining options are compression, shortcuts, and uncomfortable trade-offs.

A different way to think about readiness

The organizations that navigate this transition successfully will prioritize clarity over immediate upgrades.

Modernization at scale requires an accurate understanding of what actually matters in production before attempting to move it forward. Without that visibility, every upgrade effort inherits unnecessary complexity, consumes excess capacity, and introduces avoidable risk.

The goal is not simply adopting better tools, but reducing the structural load enterprises carry into modernization. Leaner systems modernize faster. Simpler estates scale better. Complexity compounds under time pressure.

The timeline is already set

The Java modernization crunch is a timing problem that is already locked in.

Enterprises that treat the next few years as business-as-usual will discover that sequential plans cannot survive compressed timelines. Those that confront technical debt now—before the pressure hits—will find the coming transition difficult but manageable. Those that don’t will face rushed decisions and permanent trade-offs.

By the time 2029 arrives, the window for gradual modernization will have closed. The calendar won’t wait for us to be ready.

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New Tech Forum provides a venue for technology leaders—including vendors and other outside contributors—to explore and discuss emerging enterprise technology in unprecedented depth and breadth. The selection is subjective, based on our pick of the technologies we believe to be important and of greatest interest to InfoWorld readers. InfoWorld does not accept marketing collateral for publication and reserves the right to edit all contributed content. Send all inquiries to doug_dineley@foundryco.com.

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Modern AI systems have evolved beyond the simple chatbots that quickly became popular. Now they use semantic tools to manage workflows and link machines to machines, providing a flexible and effective framework for the next generation of business automation. What you used to build in Microsoft’s Power Platform or construct inside Biztalk is now an agent, built around large language models (LLMs) that can parse both your data and the APIs that you want to use your data with, orchestrating workflows with a level of autonomy that traditional tooling can’t match.

That shift has offered new opportunities, much like those that came with business platforms like Microsoft Dynamics and Salesforce. Here, tools built to solve one set of business problems could be turned into applications that could be sold to other companies. What worked for you to solve one of your problems could now be an added revenue stream, sold through platform marketplaces that helped customers manage installations and customizations.

Agents are business applications now

Modern agents are much like those business applications. Often developed to solve a specific need, but quicky adopted by organizations and refactored to apply enterprise standards (using tools like the Agent Governance Toolkit and frameworks like Microsoft’s Agent Framework), they’re rapidly maturing and are ready to be shared more widely. The process of sharing needs to be curated and controlled, and, if possible, tied to a revenue stream.

There’s certainly some urgency here. Until recently, subsidized tokens have kept costs artificially low. Now companies like GitHub and Anthropic are moving to a more sustainable (for them) pricing model, increasing the cost of inferencing and squeezing companies’ AI budgets. As a result, switching AI projects away from a cost to a revenue source is high on CIOs’ agendas. If those tuned and trained agents can be sold on a marketplace, then that token budget can be justified.

Microsoft has always been a company built on partner relationships, starting with individual developers and working all the way up to the largest software companies and consultancies. That reach is key to helping partners extract as much value as possible from their agents, as it allows Microsoft to integrate its partner sales tools into its own products and services, as well as into other platforms.

Extending the Microsoft Marketplace for AI developers

We’re already familiar with many of Microsoft’s marketplaces, built into individual tools like Teams, into platforms like Microsoft 365 or Visual Studio, or into the Windows Store. Now the company is doing the same for AI developers, extending Microsoft Marketplace to software agents. Announced at Build 2026, the updated Microsoft Marketplace provides ways to publish code—apps and agents—developed across all of Microsoft’s development platforms, including Copilot Studio, opening the marketplace up to traditional and non-traditional developers alike.

Perhaps the most important aspect of this new Marketplace is its own intelligence, using context to expose your code to the right audience. If you’ve developed an agent for use with Microsoft 365, it will be exposed inside the Microsoft 365 Copilot Agent Store; for Visual Studio, in the Visual Studio Marketplace; or for Teams, in the Microsoft Marketplace. All of these are different views on the same back end, using AI to ensure that the relevant agents are displayed.

Replacing search with Intelligent Discovery

This is extended by another new service, Intelligent Discovery, which adds natural language support to search, using AI to infer user intent and highlight the most relevant tools. Building on the familiar metaphor of the search bar, the initial smart search model offers a freeform way to explore the Marketplace. While there are suggested prompts, they’re not necessary. The search tooling allows you to generate comparisons between tools using your own criteria, with the Marketplace AI generating views based on your requirements.

Microsoft’s aim here is to shift discovery from keywords to use cases, so that buyers can quickly get the tools they need without having to evaluate different solutions, before completing a purchase. By handing that aspect of the buying process over to Marketplace’s AIs, customers can go straight to trials or even to buying agents and applications.

For a tool like this to be successful it needs to be trustworthy. By building it on top of the same development frameworks as your agents, Microsoft can take advantage of the AI guardrails built into Microsoft Foundry as well as low-level tooling like the Agent Governance Framework. Restricting the intelligent search to the Marketplace catalogue reduces the risk of hallucination, as output is grounded in Marketplace data and metadata.

A developer-friendly marketplace

Microsoft is providing tooling to help developers get their listings right. According to Cyril Belikoff, Microsoft’s vice president of Commercial Cloud and AI, “We actually have a separate AI tool that we give to software companies to optimize their listings, called a listing optimizer, funny enough, and that listing optimizer reviews their listing and then provides them with particular guidance on how to best improve it, so that it can be best discoverable in today’s search world.”

You can expect the listing optimizer to be tuned to work with the new Marketplace tooling, but for now it still focuses on traditional search. As Marketplace is a B2B platform, there’s a lower risk of spam applications, but even so, Microsoft remains aware of the possibility of a new system being gamed, and will be rolling out Intelligent Discovery carefully, monitoring its performance as more customers get access over time.

Having a new discovery method is one thing; getting quality AI applications in the Marketplace is another. Microsoft is validating all code submitted, though the criteria will differ between target platforms. An agent built for Teams will be treated differently than one built on Microsoft 365’s WorkIQ. It’s an approach that allows Microsoft to support new standards as they become available.

Alongside its agent development tooling, Microsoft is rolling out a new set of guidelines and processes to help developers get ready to sell their agents. Hosted on GitHub, these offer code templates as well as a link to the App Advisor guidance tools.

Still gaps to fill

This first release of Intelligent Discovery is promising, but some key features are missing. With agent token costs an increasing problem for businesses, it would be nice to see tools that help predict costs, integrating with finops tooling. We’re living in an age of shadow AI, and putting the AI we used to buy with credit cards in Microsoft Marketplace is one way to shine a light on those shadows — bringing the necessary control and governance to AI purchases, and maybe even providing support for site licensing.

Microsoft Marketplace is becoming a useful resource for AI application developers. It encompasses the entire development life cycle: offering tools that can help you build agents, the models that you need to power your agents, and finally a way to monetize your work. There’s a longer-term opportunity here, for both the Marketplace and Intelligent Discovery to offer Model Context Protocol (MCP) interfaces, ensuring that tooling and tool discovery become part of the developer workflow, and making developers aware of new tools that might help solve a problem or simplify a task.

The ability for attackers to leverage automatic install script execution in npm will finally come to an end when expected changes arrive from GitHub in July. Coders will still be able to enable the function, but the default setting will block it. 

In V12, default settings are changing, GitHub said in its changelog, noting, “it turns an npm install behavior that runs automatically today into one you explicitly opt into.” 

Specifically, the post said, “allowScripts defaults to off: npm install will no longer execute preinstall, install or postinstall scripts from dependencies unless they are explicitly allowed in your project. This includes native node-gyp builds; a package with a binding.gyp and no explicit install script still gets blocked, because npm runs an implicit node-gyp rebuild for it. Prepare scripts from git, file, and link dependencies are blocked the same way.”

Analysts, consultants, and users generally applauded the change, but said that it would only narrow the exposure to supply chain attacks instead of eliminating it. 

Attacks likely to move elsewhere

Sonu Kapoor, maintainer for CVE Lite CLI in the OWASP Incubator Project, said that this change is likely to force the supply chain attacks that leveraged the automatic execution to move elsewhere.

“This does not eliminate npm supply chain risk, it removes a major automatic execution path,” Kapoor said. “Attackers can still move to other paths: malicious package code that runs at application runtime, compromised maintainer accounts, dependency confusion, typo-squatting, poisoned GitHub Actions workflows, malicious transitive dependencies, or stolen publishing tokens. This closes one very dangerous door, but it does not secure the whole house.”

Still, attacks leveraging the setting have been regularly used in supply chain attacks. 

However Alan Parkinson, director of secure medical device firm Threat Detective, said more sophisticated attackers have already moved beyond this hole. 

“The install script attack vector has been known for years,” Parkinson said. “Most security teams marked it as low risk and moved on to higher risk threats. What raised its profile wasn’t the technical exploitability changing, it was a run of high-profile victims and some threat actors openly chasing notoriety.”

He added, “the pre and post install scripts was never a clever attack vector to begin with. Running code from an install hook is crude and noisy, which is why it caused such visible damage. The more capable actors are already moving to other methods, so v12 mainly shuts the door on less sophisticated threat actors.”

Although GitHub declined an interview, Zach Steindler, a GitHub principal engineer, answered InfoWorld’s questions by email. He said the volume and pace of supply chain attacks forced the default settings change. 

“We’ve seen attackers target these capabilities to quickly propagate attacks from one compromised package to many. Years of security and usability research have shown that it’s not enough to make secure functionality available; the secure path has to be the default in order for it to be widely adopted,” Steindler said.

He added, “we believe that these changes are a great way to provide high impact secure defaults while still providing the option for some users to fall back on functionality they might need in some circumstances.”

Change overdue

Sanchit Vir Gogia, chief analyst at Greyhound Research, said that GitHub was the last of the repositories to make the setting default change. “Rivals moved first: Yarn, pnpm and Bun all block third party install scripts by default in their own ways,” Gogia said. “Npm is not inventing a new doctrine. It is finally adopting one.”

Steindler didn’t dispute Gogia’s comment. 

“It’s not easy being the stewards of the largest package repository in the world. Community consensus on what security capabilities should be standard, and when it’s okay to make breaking changes shifts over time. From our continual conversations with the community, it was clear it was time to make this change,” Steindler said.

“The recent attacks are alarming,” he noted, “but stewarding these package repositories is a multi-decade effort, not just a moment in time. As attacks evolve, so will our defensive security capabilities. We’re in this for the long haul.”

Gogia said that the change, although overdue, is a good one. 

“Npm is removing one of the most comfortable hiding places for software supply chain risk: code that executes the moment a developer types install,” Gogia said. “With npm v12, execution becomes something that must be approved, recorded in the project, and committed for review. That is not a design adjustment. It is a change in control philosophy.”

Bad defaults become infrastructure

Gogia had his own take on why GitHub waited so long.

“Npm waited because its risky default acquired a constituency. As far back as 2016, npm’s own position was that the convenience of install scripts outweighed the worm risk, with an opt-out flag for the cautious. The trade-off was a documented product decision, not an oversight,” he said.

“The trouble with bad defaults is that they become infrastructure,” he added. “Native module builds, browser installers such as Playwright and Cypress, Electron download flows and Husky hooks all grew around automatic execution. Turning it off became less a technical adjustment and more a constitutional reform.”

Liability changed hands

The real pressure for the change, however, came from regulators.

“The deeper answer is that the liability changed hands. Once regulation such as the EU Cyber Resilience Act and securities disclosure rules placed supply chain failure on corporate balance sheets, a documented unsafe default became indefensible,” Gogia said. 

Kapoor agreed that long-used procedures enabled this security hole to survive longer than it should have. 

“The reason this likely was not done long ago is compatibility,” he said. “Install scripts are not only used by attackers. Many legitimate packages use them to compile native modules, download platform-specific binaries, generate files, or complete setup steps. Changing the default breaks assumptions that have existed in the npm ecosystem for years. That is why these security changes often arrive slowly. The safer default is obvious from a security perspective, but painful from an ecosystem compatibility perspective.”

In addition, he noted, “the bigger point is that package managers are moving from implicit trust to explicit trust. That is the right direction. Developers should have to approve which dependencies are allowed to execute code during install. But approval cannot become a blind checkbox. Teams need visibility into which package wants to run a script, whether it is direct or transitive, why it is there, and whether it belongs in the project at all.”

Kapoor added that this change matters because install-time execution often happens in privileged environments with access to tokens, secrets, internal registries, build artifacts, or deployment paths. “Even if the script does not compromise production directly, it may be able to steal enough context to support the next stage of an attack,” he said.

Value in the pain

Cybersecurity consultant Brian Levine, executive director of FormerGov, agreed that the closing of this security hole is a very good thing. 

“It seems like virtually every major supply chain attack of the last decade has had the same original sin: code that ran automatically because the ecosystem let it. Npm finally closing that door by default is overdue, but it’s genuinely significant. This is the package manager for hundreds of billions of downloads a month,” Levine said.

“When npm changes its defaults, it changes the security posture of practically every enterprise dev environment on the planet. It may have been the last large code repository to still allow this kind of automated execution.”

Levine added that this change might not merely stop a security hole, but the new process may meaningfully improve security. 

“There’s actually something valuable buried in this migration pain. Having developers explicitly approve which packages can run code and commit that list to source control is a form of software supply chain governance that many organizations never had,” Levine said. “It creates an auditable record which is meaningful, especially for regulated industries.”

Of all the reasons Python is a hit with developers, one of the biggest is its broad and ever-expanding selection of third-party packages. Convenient toolkits for everything from ingesting and formatting data to high-speed math and machine learning are just an import or pip install away.

But what happens when those packages don’t play nice with each other? What do you do when different Python projects need competing or incompatible versions of the same add-ons? That’s where Python virtual environments come into play.

What are Python virtual environments?

A virtual environment is a way to have multiple, parallel instances of the Python interpreter, each with different sets of packages and different configurations. Each virtual environment contains a discrete copy of the Python interpreter, including copies of its support utilities (such as the package manager pip).

The packages installed in each virtual environment are seen only in that virtual environment and no other. Even large, complex packages with platform-dependent binaries can be corralled off from each other in virtual environments.

Why use Python virtual environments?

There are a few common use cases for a virtual environment:

1. You’re developing multiple projects that depend on different versions of the same packages, or you have a project that must be isolated from certain packages because of a namespace collision. This is the most standard use case.
2. You’re working in a Python environment where you can’t modify the site-packages directory. This may be because you’re working in a highly controlled environment, such as managed hosting, or on a server where the choice of interpreter (or packages used in it) can’t be changed because of production requirements.
3. You want to experiment with a specific combination of packages under highly controlled circumstances, for instance to test cross-compatibility or backward compatibility.
4. You want to run a “baseline” version of the Python interpreter on a system with no third-party packages, and only install third-party packages for each individual project as needed.

Nothing says you can’t simply unpack a Python library into a subfolder of a project and use it that way. Likewise, you could download a standalone copy of the Python interpreter, unpack it into a folder, and use it to run scripts and packages devoted to it.

But managing such cobbled-together projects soon becomes difficult. It only seems easier to do that at first. Working with packages that have binary components, or that rely on elaborate third-party dependencies, can be a nightmare. Worse, reproducing such a setup on someone else’s machine, or on a new machine you manage, is tricky.

The best long-term solution is to use Python’s native mechanisms for creating, reproducing, and working with virtual environments.

How to use virtual environments in Python 3

Python has native tooling for virtual environments that makes the whole process quite simple. This wasn’t always the case, but now all supported versions of Python use the native virtual environment tool, venv.

Create the Python virtual environment

To create a virtual environment in a given directory, type:

python3 -m venv /path/to/venv

For instance, to create the virtual environment in the current directory, using the subdirectory .venv type:

python3 -m venv .venv

On Microsoft Windows, you can use py instead of python3 to reliably access an installed Python version. (See this article for more about using the py launcher in Windows.)

The exact name for the virtual environment directory is arbitrary, but it’s typically .venv.

The whole process of setting up the virtual environment may take a minute or two. When it’s finished, you should see that directory with a few subdirectories in it. The most important subdirectory is bin on Unix or Scripts on Windows, which is where you’ll find the copy of the Python interpreter for the virtual environment along with its utilities.

Note that because each virtual environment contains its own copy of the Python interpreter, it can be fairly large. A Python 3.13 virtual environment will consume anywhere from 14MB to 26MB of disk space, depending on the operating system.

Venvs and version control

If you are setting up a virtual environment in a project directory managed with some kind of version control system (e.g., Git), exclude the environment directory from tracking before you make any commits after creating the venv.

Venvs should not be tracked along with their associated code, as they are meant to be destroyed and recreated as needed. You should, however, track the requirements.txt or pyproject.toml files associated with the project, as those are used to describe what gets installed in the venv for that project.

Activate the Python virtual environment

Before you can use this virtual environment, you need to explicitly activate it. Activation makes the virtual environment the default Python interpreter for the duration of a shell session.

You’ll need to use different syntax for activating the virtual environment depending on which operating system and command shell you’re using.

• On Unix or MacOS, using the bash shell: source /path/to/venv/bin/activate
• On Unix or MacOS, using the csh shell: source /path/to/venv/bin/activate.csh
• On Unix or MacOS, using the fish shell: source /path/to/venv/bin/activate.fish
• On Windows using the Command Prompt: path/to/venv/Scripts/Activate.bat
• On Windows using PowerShell: path/to/venv/Scripts/Activate.ps1

Note that the activated environment only works for the context it was activated in. For instance, if you launch two instances of PowerShell, A and B, and you activate the virtual environment in instance A, that environment will apply only to A, not B.

Many Python IDEs will automatically detect and activate a virtual environment if one is found in the current project directory. Visual Studio Code, for instance, can do this when the Python extension is enabled. Opening a terminal inside Visual Studio Code will automatically activate the selected virtual environment. PyCharm automatically creates a virtual environment for each new project and enables it automatically.

Configure and use the Python virtual environment

Once you’ve activated the new virtual environment, you can use the pip package manager to add and change packages for it. You’ll find pip in the Scripts subdirectory of the virtual environment on Windows, and in the bin subdirectory on Unix OSes.

If you’re already familiar with the way pip works, you’re set. It should be just the same in a virtual environment. Just make sure you’re using the instance of pip that manages packages for the virtual environment in the context where it was activated—e.g., the bash session or Windows CLI/PowerShell session. If you want to verify that you’re using the right pip and the right virtual environment, type pip -V and check that the path it displays points to a subdirectory of your virtual environment.

Note that when you want to upgrade pip in a virtual environment, it’s best to use the command python3 -m pip install -U pip. This ensures the upgrade process is run in such a way that Python doesn’t lock crucial files. The command pip install -U pip may not be able to complete the upgrade properly.

To use the virtual environment you created to run Python scripts, simply invoke Python from the command line in the context where you activated it. For instance, to run a script, just run python3 myscript.py.

With PyCharm, you can use the IDE’s own package management interface to manage the packages installed in your project.

Managing packages in Python virtual environments

When you create a new virtual environment, pip will be installed, but that’s all. You’ll need to install any other packages you want to use in the environment. For projects with complex requirements, it is customary to keep in the root of the project a requirements.txt file that lists the requirements for the project. This way, if you need to recreate the virtual environment, you can reinstall all of the needed packages with the command pip install -r requirements.txt.

More recently, a new project metadata format has emerged for Python projects, called pyproject.toml. A pyproject.toml file contains the package requirements of the project, but also a great deal of other information about it. To install those requirements, you’d run pip install . in the same directory as the pyproject.toml file.

Note that the copy of pip that lives in a virtual environment is local to that virtual environment. Each virtual environment has its own copy, which will need to be updated and maintained independently. This is why you may get warnings about pip being out of date in some virtual environments but not others; pip has to be updated in each virtual environment separately.

Deactivating the Python virtual environment

When you’re done using the virtual environment, you can just terminate the session where you were using it. If you want to continue to work in the same session but with the default Python interpreter instead, type deactivate at the prompt. Windows users on the Command Prompt need to run deactivate.bat from the Scripts subdirectory, but Unix users and Windows users running PowerShell can simply type deactivate in any directory.

Removing the Python virtual environment

Virtual environments are self-contained. When you no longer need the virtual environment, you can simply delete its directory. Just make sure you first close any running copies of Python that use the virtual environment.

Whenever you want to refresh or recreate a virtual environment, you can simply delete the current environment directory and recreate the venv as described above (see “Managing packages in Python virtual environments”). This is typically the easiest way to upgrade a project to a newer version of Python: delete or temporarily re-name the venv directory (in case the new version doesn’t work), then create a new one and install the project requirements into it.

If you have many older projects that aren’t being actively used, you can remove their environments to save space. They can be recreated easily whenever needed, although you will want to note which version of Python was used to create them along with the needed packages (typically recorded in requirements.txt or pyproject.toml).

Relocating the Python virtual environment

It’s tempting to assume a virtual environment can be copied and moved around along with its project. Don’t do this. Virtual environments are tied to the location of the Python installation on the system where they’re created. If you want to move the project to another system, leave out the venv directory, and recreate the venv on the target machine. Do copy and move the requirements.txt or pyproject.toml file with the project, because those files are needed to recreate the venv on the other system.

How to use virtual environments in Python 2

With Python 2, virtual environments aren’t a native feature of the language. Instead, you need to install third-party libraries to create and manage virtual environments.

The most popular and widely used of these projects is virtualenv, which handles creating the directory structure and copying the needed files into a virtual environment. To install virtualenv, just use pip install virtualenv. To create a virtual environment directory with it, type virtualenv /path/to/directory. Activating and deactivating the virtual environment works the same way as it does for virtual environments in Python 3 (see above).

Note that Python 2 should not be used for any new development. Virtual environments in Python 2, like Python 2 itself, should be used only for the maintenance of legacy projects that should eventually be migrated to Python 3.

Virtual environments and the main Python package directory

Normally, when you create a venv, it cannot work with the packages already present in the Python installation that created it. This is by design, as it ensures that packages installed globally don’t interfere with local ones.

You can override this behavior, but only when you first create a virtual environment. If you pass the flag --system-site-packages to venv when you run it, the created venv will have access to the parent Python’s package directory.

Using Python virtual environments with Jupyter notebooks

If you’re using Jupyter notebooks (aka IPython notebooks), and you already have Jupyter installed systemwide, create your virtual environment and activate it. Then, from your virtual environment directory, run pip install ipykernel to add the needed components for IPython. Finally, run ipython kernel install —user —name=, where project_name is a name you want to associate with that particular project. From there you should be able to launch Jupyter and switch to the IPython kernel you installed inside the virtual environment.

Upgrading Python virtual environments

When you upgrade a Python runtime on your system, virtual environments that use that version of Python aren’t automatically upgraded. That’s your responsibility. And that’s by design, because unwitting upgrades to Python versions can break their attendant packages.

If you’ve upgraded an existing Python interpreter with a minor point upgrade—e.g., from Python 3.13.1 to Python 3.13.3—you can upgrade any corresponding virtual environments easily enough. From a command prompt in the project directory, enter:

python -m venv /path/to/venv --upgrade

Don’t activate the virtual environment beforehand, or the upgrade may not work.

Alternatively, as noted above (see “Removing the Python virtual environment”), you could elect to remove the venv completely and recreate it using your requirements.txt or pyproject.toml file.

If you’ve installed a major new version of Python—e.g., you already have Python 3.10 and you now install Python 3.11 alongside it—you’ll need to create a new virtual environment that specifically uses the new major point version. Do not attempt to upgrade an existing virtual environment to a higher major point version of Python.

Too many enterprises remain ignorant of the European Union’s 2024 Cyber Resilience Act, the first elements of which enter force on June 11, according to a new survey.

Two-thirds of respondents to the survey by Open Source Security Foundation said they were unfamiliar with the CRA, which aims to make hardware and software sold in the EU more secure.

As well as the CRA’s demands on vendors, it also has implications for users of open-source software, hence the Foundation’s interest in the topic. Among other measures, the CRA creates the role of open-source steward within the enterprise, with responsibility for ensuring that a security policy is in place for any software being used within the organization.

The first part of the CRA to enter force, on June 11, concerns the designation of conformity assessment bodies by member states. Then, from September 11, manufacturers will be required to begin reporting vulnerabilities in their products to the relevant authorities. The remaining obligations under the Act, which include substantial financial penalties, will apply from December 11, 2027.

The impending sanctions seem not to have concerned businesses: 56 percent of respondents to the OpenSSF survey were unaware that non-compliance fines could reach €15 million or 2.5 percent of global annual turnover.

The lack of knowledge about the implications of the Act surprised OpenSSF CTO Christopher Robinson. “We’ve been speaking on this topic for some time and we’re scratching our heads on why more companies are not aware of the implications of the Act,” he said.

Global concern

He surmised that some companies don’t think EU regulations on hardware and software security apply to them — but such concerns will soon be a global matter. “Other countries, like Japan, are considering similar laws,” he said.

One area of misunderstanding could be that the CRA applies to vendors, and their customers may think that the requirements under the Act didn’t apply to them. He said that this was a misguided approach, particularly when the CRA’s application to open-source software is taken into account.

“There are about 700 million projects in Git Hub. If you work for an organization like a bank, you have little idea which of those projects are being used,” he said.

Under the Act, software companies will have to supply a software bill of materials (SBOM) that has been passed as secure, he said.

Companies that supply US federal government organizations already face this requirement, he said: “If you’re selling to the US government — which is the largest customer on the planet – you should be providing an SBOM.”

Cybersecurity consultant Hans Study said that by addressing the supply chain issue, the CRA is a step in the right direction. “Almost every application has dependencies, whether that is free and open-source software, commercial packages, or some mix of both. The problem has always been responsibility, and the blame game that comes with it. What the CRA does is make it harder for companies to dodge that responsibility when they are building, selling, or placing products with digital elements on the market,” he said.

AI ignorance

According to Michael Callahan, VP of Cyber Strategy at Salt Security, one of the issues that could cause problems in the future is the growing use of AI in the software development process. “The Cyber Resilience Act assumes enterprises know what is in their software. That assumption breaks down when AI coding assistants are generating a significant share of code. An AI assistant has never read your organization’s security policies, your licensing obligations, or your open-source governance standards. The code it produces may contain dependencies, patterns, or vulnerabilities that your security team cannot easily trace back to a specific decision or a specific developer.”

Enterprises are quickly running out time to fix issues and many are pessimistic about their chances. According to the OpenSSF survey, only 41percent of manufacturers expect to be fully compliant by December 2027, while 39 percent do not know when they will be.

It may be that the proposed fines could concentrate minds. Robinson said that it could be like GDPR where a few heavy fines drew companies’ attention to the regulation. The upper limit on fines is per infraction, not per company, he said: “Something like that could wipe out an SME and seriously hit large corporations.” The legislation should be something that all businesses need to be aware of, but there is still a long way to go.

This article first appeared on CIO.

I’ve been around long enough to remember when deploying an application meant copying a *.exe file from the developer’s machine right into production. I am not making this up. It was that simple, and that fraught with peril. Applications weren’t complex — they were often not anything more than that simple *.exe file — and the process around deployment didn’t need to be anything complex, but it probably should have been.

Proper deployment of an application is something we’ve learned to do over the years. The process of properly building, testing, and deploying an application has grown more complex for two reasons. First, the process must ensure that every deployment succeeds. Deploying complex applications can be convoluted and challenging, and a strict deployment process ensures everything happens properly and runs correctly. Second, the process must thoroughly test the application to make sure that all the moving parts work together to create a properly functioning application. 

Today’s continuous deployment processes were hard-won from many lessons learned. Eventually, these practices became formalized, even to the point where the Sarbanes-Oxley Act was understood to require that IT departments formally document their deployment processes. 

This kind of governance is what separates professional software development organizations from those that, well, don’t know what they are doing. 

Agentic growing pains

Agentic development is headed in this same direction, but it’s all happening a bit more quickly. It was just a few months ago that people began to use AI to write code seriously. At first, most of us were doing it furtively, having Claude Code find and fix bugs, and then quietly checking in the solutions. Maybe we were a bit hesitant to mention that we had done this, but then we felt guilty about doing it and taking credit, and eventually we mentioned it. But it soon became apparent — like “within a week” soon — that Claude Code was up to the task, and we became pretty open about it. 

Very quickly, it not only became accepted but actually encouraged, and we were off to the races. In a month, everyone was tokenmaxxing.

It almost seems a bit out of control. Sure, there is a lot of code being generated and non-trivial amounts of money being spent, but it isn’t quite clear if the results are worth the effort. I’m not at all sure if anyone can say that the money spent is returning the value needed.

At some point, as an industry, we are going to have to get control of all of this. I fear that there will be a rush to impose governance over the whole thing. This, like deploying an .exe directly, is also fraught with peril. Right now, there appears to be little control over what tools are being used where, how much is being spent for what purpose, and what that spending is actually getting us. 

The governance over our deployment processes was successful and useful because it arose organically. The accepted, codified procedures arose from the lessons that practitioners learned by actually building and deploying applications. We all should work to ensure that a similar process happens with agentic coding.

Developers know best

Because agentic coding is happening so quickly and so furiously, the danger is that a governance process will be imposed over the top just as quickly and furiously. I want to encourage us all to take a deep breath, slow down a bit, and take a close look at what we are doing, and more importantly, how we are doing it. 

Agentic coding will be governed in some manner. It’s critical that we practitioners take the lead in providing that governance, or we’ll have governance forced upon us. We are the ones that know what matters and how the tools should be used. We are the ones with skin in the game and the ones keeping pace with the technology. 

Top-down governance of a technology moving this fast will never be able to keep up. Or as Uri Haramati, co-founder and CEO of Torii says, “The person closest to the tool usually understands why it’s being used, and governance works better when it includes those people instead of trying to control them.”

Copying that *.exe file into production is comically reckless. We don’t do that anymore because we know better. It took time, but we learned the right way to deploy software. Right now, we are in the “copying the *.exe” phase of agentic coding, and we need to figure out the right way to do it before someone comes along and does it for us.

AI-generated code is riddled with security flaws, yet enterprises are shipping more of it than ever before. Why? Perhaps they’re over-confident, lack true visibility into security risks, or are simply choosing to ignore the problem and hope it goes away.

It’s a dangerous game to play at the dawn of the agentic AI era, as underscored in a new report from app security company Checkmarx.

The survey of thousands of security leaders exposes an underlying naivete about AI-built code and its vulnerabilities, even as tools like Anthropic’s Mythos are uncovering security flaws orders of magnitude faster than any human security team could ever hope to.

“Mythos-class models collapse the window between a vulnerability existing and a working exploit being available from months to minutes,” the report notes. Enterprises relying on traditional security tools and methods, it says, “cannot survive this reality.”

Security as an afterthought

Checkmarx’s survey of 2,350 CISOs, AppSec managers, and developers across 14 countries focused on how much AI-developed code enterprises are deploying, the vulnerabilities it introduces, how it impacts developer workflows, and overall sentiment about AI code and security posture.

Today, nearly half of production code is AI-generated, and the majority of enterprises also report that at least half their codebase is made up of open-source components, according to the report.

But the more AI-generated code that is pushed out, the more vulnerabilities are exposed. Enterprises who said 81% – 100% of their code is built by AI ship vulnerable code 3.4 times more often than businesses using AI more conservatively, relying on 20% or less AI code.

Additionally, 70% of developers said that AI code generation created vulnerabilities in 2025, and almost all enterprises surveyed (93%) had at least one security breach as a direct result of in-house developed apps.

Still, risk is becoming “normalized,” the report notes, with three-quarters of enterprises knowingly deploying vulnerable code as they face increased pressure for ROI. Startlingly, about 30% of respondents admitted they ship compromised code and hope the vulnerability won’t be found. Similarly, more than a third of organizations leave half of their known vulnerabilities unfixed for 90 days or more.

The report points out that the organizational bottleneck isn’t detection, “it’s the human decision to ship anyway, suppress the finding, or defer to the next sprint.”

Along with this, AppSec teams are often limited to reactive incident response as they deal with tool sprawl. And developers only continuously secure code a small percentage of the time (18%), even though nearly all are equipped with security tooling.

Ultimately, developers are “set up to fail,” the report contends. They face significant pressure to deliver, and are forced to choose quantity and speed over security. Yet, even as they face significant consequences when it comes to post-mortems, performance reviews, escalation, and blocked releases, the tools that contribute to security issues, delivering low-value findings, unclear guidance, or late feedback, continue to go unfixed.

“Developers remain accountable for outcomes, even when systems and workflows are not aligned to support them,” the report notes.

Overconfidence, outdated practices

Alarmingly, many enterprises seem to be deluded when it comes to their security posture. Of those that rate themselves as “highly mature” AI organizations, 42% often ship the most vulnerable code, and have breach rates “barely distinguishable” from other enterprises.

“Confidence isn’t protecting them,” the report notes. “It’s blinding them.”

Underscoring this, only 22% of organizations have formal AI governance, and developers still rely on manual code reviews to ensure their code meets compliance standards.

The result is a mismatch between the speed of software creation and the speed of governance, the report notes. “Compliance frameworks are evolving, but many organizations are still attempting to govern AI-scale development with processes designed for a slower era of software delivery.”

Strategic imperatives for enterprises

Enterprises do seem to have wised up (a bit) after Anthropic’s Mythos proved capable of not only discovering vulnerabilities across major operating systems and browsers, but exploiting them 100 times faster than previous Claude models. And the subsequent Project Glasswing almost immediately surfaced thousands of previously-unidentified security flaws.

Checkmarx’s survey, which, it should be noted, was conducted a month prior to Mythos’ arrival, found that enterprises are finally taking proactive measures, focusing more heavily on AI security threats overall, and investing more in DevSecOps practices, automation, and developer training.

The report emphasizes the importance of prioritizing risk over code volume; vulnerabilities should not be considered isolated incidents. Also, it’s critical to embed security into developer workflows rather than treating it as a checkpoint. Enterprises must have systems that reduce noise, provide clear guidance, and allow them to take action when an issue arises.

Security “must be integrated directly into how developers write, test, and ship code within the IDE, pipelines, and AI-assisted workflows where development now happens,” the report notes.

Similarly, enterprises would benefit by reducing fragmentation and tool sprawl and defining ownership of the AI tools. By simplifying security stacks, they can align responsibilities and ensure consistent tool use, according to the report.

Further, AI needs strong governance, and teams must move beyond outdated manual triage and “human-gated remediation.” AI can fight AI in a strong system built to prioritize, remediate, and resolve risk “without waiting for a human to approve each step,” the report notes.

Ultimately, it says: “Progress depends on embedding intelligence directly into workflows, enabling risks to be prioritized, remediated, and resolved, all within the systems that they operate in.”

This article originally appeared on CIO.com.

Of all the reasons Python is a hit with developers, one of the biggest is its broad and ever-expanding selection of third-party packages. Convenient toolkits for everything from ingesting and formatting data to high-speed math and machine learning are just an import or pip install away.

But what happens when those packages don’t play nice with each other? What do you do when different Python projects need competing or incompatible versions of the same add-ons? That’s where Python virtual environments come into play.

What are Python virtual environments?

A virtual environment is a way to have multiple, parallel instances of the Python interpreter, each with different sets of packages and different configurations. Each virtual environment contains a discrete copy of the Python interpreter, including copies of its support utilities (such as the package manager pip).

The packages installed in each virtual environment are seen only in that virtual environment and no other. Even large, complex packages with platform-dependent binaries can be corralled off from each other in virtual environments.

Why use Python virtual environments?

There are a few common use cases for a virtual environment:

1. You’re developing multiple projects that depend on different versions of the same packages, or you have a project that must be isolated from certain packages because of a namespace collision. This is the most standard use case.
2. You’re working in a Python environment where you can’t modify the site-packages directory. This may be because you’re working in a highly controlled environment, such as managed hosting, or on a server where the choice of interpreter (or packages used in it) can’t be changed because of production requirements.
3. You want to experiment with a specific combination of packages under highly controlled circumstances, for instance to test cross-compatibility or backward compatibility.
4. You want to run a “baseline” version of the Python interpreter on a system with no third-party packages, and only install third-party packages for each individual project as needed.

Nothing says you can’t simply unpack a Python library into a subfolder of a project and use it that way. Likewise, you could download a standalone copy of the Python interpreter, unpack it into a folder, and use it to run scripts and packages devoted to it.

But managing such cobbled-together projects soon becomes difficult. It only seems easier to do that at first. Working with packages that have binary components, or that rely on elaborate third-party dependencies, can be a nightmare. Worse, reproducing such a setup on someone else’s machine, or on a new machine you manage, is tricky.

The best long-term solution is to use Python’s native mechanisms for creating, reproducing, and working with virtual environments.

How to use virtual environments in Python 3

Python has native tooling for virtual environments that makes the whole process quite simple. This wasn’t always the case, but now all supported versions of Python use the native virtual environment tool, venv.

Create the Python virtual environment

To create a virtual environment in a given directory, type:

python3 -m venv /path/to/venv

For instance, to create the virtual environment in the current directory, using the subdirectory .venv type:

python3 -m venv .venv

On Microsoft Windows, you can use py instead of python3 to reliably access an installed Python version. (See this article for more about using the py launcher in Windows.)

The exact name for the virtual environment directory is arbitrary, but it’s typically .venv.

The whole process of setting up the virtual environment may take a minute or two. When it’s finished, you should see that directory with a few subdirectories in it. The most important subdirectory is bin on Unix or Scripts on Windows, which is where you’ll find the copy of the Python interpreter for the virtual environment along with its utilities.

Note that because each virtual environment contains its own copy of the Python interpreter, it can be fairly large. A Python 3.13 virtual environment will consume anywhere from 14MB to 26MB of disk space, depending on the operating system.

Venvs and version control

If you are setting up a virtual environment in a project directory managed with some kind of version control system (e.g., Git), exclude the environment directory from tracking before you make any commits after creating the venv.

Venvs should not be tracked along with their associated code, as they are meant to be destroyed and recreated as needed. You should, however, track the requirements.txt or pyproject.toml files associated with the project, as those are used to describe what gets installed in the venv for that project.

Activate the Python virtual environment

Before you can use this virtual environment, you need to explicitly activate it. Activation makes the virtual environment the default Python interpreter for the duration of a shell session.

You’ll need to use different syntax for activating the virtual environment depending on which operating system and command shell you’re using.

• On Unix or MacOS, using the bash shell: source /path/to/venv/bin/activate
• On Unix or MacOS, using the csh shell: source /path/to/venv/bin/activate.csh
• On Unix or MacOS, using the fish shell: source /path/to/venv/bin/activate.fish
• On Windows using the Command Prompt: path/to/venv/Scripts/Activate.bat
• On Windows using PowerShell: path/to/venv/Scripts/Activate.ps1

Note that the activated environment only works for the context it was activated in. For instance, if you launch two instances of PowerShell, A and B, and you activate the virtual environment in instance A, that environment will apply only to A, not B.

Many Python IDEs will automatically detect and activate a virtual environment if one is found in the current project directory. Visual Studio Code, for instance, can do this when the Python extension is enabled. Opening a terminal inside Visual Studio Code will automatically activate the selected virtual environment. PyCharm automatically creates a virtual environment for each new project and enables it automatically.

Configure and use the Python virtual environment

Once you’ve activated the new virtual environment, you can use the pip package manager to add and change packages for it. You’ll find pip in the Scripts subdirectory of the virtual environment on Windows, and in the bin subdirectory on Unix OSes.

If you’re already familiar with the way pip works, you’re set. It should be just the same in a virtual environment. Just make sure you’re using the instance of pip that manages packages for the virtual environment in the context where it was activated—e.g., the bash session or Windows CLI/PowerShell session. If you want to verify that you’re using the right pip and the right virtual environment, type pip -V and check that the path it displays points to a subdirectory of your virtual environment.

Note that when you want to upgrade pip in a virtual environment, it’s best to use the command python3 -m pip install -U pip. This ensures the upgrade process is run in such a way that Python doesn’t lock crucial files. The command pip install -U pip may not be able to complete the upgrade properly.

To use the virtual environment you created to run Python scripts, simply invoke Python from the command line in the context where you activated it. For instance, to run a script, just run python3 myscript.py.

With PyCharm, you can use the IDE’s own package management interface to manage the packages installed in your project.

Managing packages in Python virtual environments

When you create a new virtual environment, pip will be installed, but that’s all. You’ll need to install any other packages you want to use in the environment. For projects with complex requirements, it is customary to keep in the root of the project a requirements.txt file that lists the requirements for the project. This way, if you need to recreate the virtual environment, you can reinstall all of the needed packages with the command pip install -r requirements.txt.

More recently, a new project metadata format has emerged for Python projects, called pyproject.toml. A pyproject.toml file contains the package requirements of the project, but also a great deal of other information about it. To install those requirements, you’d run pip install . in the same directory as the pyproject.toml file.

Note that the copy of pip that lives in a virtual environment is local to that virtual environment. Each virtual environment has its own copy, which will need to be updated and maintained independently. This is why you may get warnings about pip being out of date in some virtual environments but not others; pip has to be updated in each virtual environment separately.

Deactivating the Python virtual environment

When you’re done using the virtual environment, you can just terminate the session where you were using it. If you want to continue to work in the same session but with the default Python interpreter instead, type deactivate at the prompt. Windows users on the Command Prompt need to run deactivate.bat from the Scripts subdirectory, but Unix users and Windows users running PowerShell can simply type deactivate in any directory.

Removing the Python virtual environment

Virtual environments are self-contained. When you no longer need the virtual environment, you can simply delete its directory. Just make sure you first close any running copies of Python that use the virtual environment.

Whenever you want to refresh or recreate a virtual environment, you can simply delete the current environment directory and recreate the venv as described above (see “Managing packages in Python virtual environments”). This is typically the easiest way to upgrade a project to a newer version of Python: delete or temporarily re-name the venv directory (in case the new version doesn’t work), then create a new one and install the project requirements into it.

If you have many older projects that aren’t being actively used, you can remove their environments to save space. They can be recreated easily whenever needed, although you will want to note which version of Python was used to create them along with the needed packages (typically recorded in requirements.txt or pyproject.toml).

Relocating the Python virtual environment

It’s tempting to assume a virtual environment can be copied and moved around along with its project. Don’t do this. Virtual environments are tied to the location of the Python installation on the system where they’re created. If you want to move the project to another system, leave out the venv directory, and recreate the venv on the target machine. Do copy and move the requirements.txt or pyproject.toml file with the project, because those files are needed to recreate the venv on the other system.

How to use virtual environments in Python 2

With Python 2, virtual environments aren’t a native feature of the language. Instead, you need to install third-party libraries to create and manage virtual environments.

The most popular and widely used of these projects is virtualenv, which handles creating the directory structure and copying the needed files into a virtual environment. To install virtualenv, just use pip install virtualenv. To create a virtual environment directory with it, type virtualenv /path/to/directory. Activating and deactivating the virtual environment works the same way as it does for virtual environments in Python 3 (see above).

Note that Python 2 should not be used for any new development. Virtual environments in Python 2, like Python 2 itself, should be used only for the maintenance of legacy projects that should eventually be migrated to Python 3.

Virtual environments and the main Python package directory

Normally, when you create a venv, it cannot work with the packages already present in the Python installation that created it. This is by design, as it ensures that packages installed globally don’t interfere with local ones.

You can override this behavior, but only when you first create a virtual environment. If you pass the flag --system-site-packages to venv when you run it, the created venv will have access to the parent Python’s package directory.

Using Python virtual environments with Jupyter notebooks

If you’re using Jupyter notebooks (aka IPython notebooks), and you already have Jupyter installed systemwide, create your virtual environment and activate it. Then, from your virtual environment directory, run pip install ipykernel to add the needed components for IPython. Finally, run ipython kernel install —user —name=, where project_name is a name you want to associate with that particular project. From there you should be able to launch Jupyter and switch to the IPython kernel you installed inside the virtual environment.

Upgrading Python virtual environments

When you upgrade a Python runtime on your system, virtual environments that use that version of Python aren’t automatically upgraded. That’s your responsibility. And that’s by design, because unwitting upgrades to Python versions can break their attendant packages.

If you’ve upgraded an existing Python interpreter with a minor point upgrade—e.g., from Python 3.13.1 to Python 3.13.3—you can upgrade any corresponding virtual environments easily enough. From a command prompt in the project directory, enter:

python -m venv /path/to/venv --upgrade

Don’t activate the virtual environment beforehand, or the upgrade may not work.

Alternatively, as noted above (see “Removing the Python virtual environment”), you could elect to remove the venv completely and recreate it using your requirements.txt or pyproject.toml file.

If you’ve installed a major new version of Python—e.g., you already have Python 3.10 and you now install Python 3.11 alongside it—you’ll need to create a new virtual environment that specifically uses the new major point version. Do not attempt to upgrade an existing virtual environment to a higher major point version of Python.

There is no ordained path. The hope that we were converging on some kind of consensus in web development has been eradicated by recent, ingenious developments that point in almost every direction. Yet, if there is a central theme uniting these efforts, it is the desire to mitigate the layers of liturgical embellishment that have grown up around the reactive canon. How can we look at things differently to attain the power that we need, without the heavy intricacy?

Here are eight cutting-edge web development tools that point the way.

Front-end maestro

If you put a bunch of classical musicians in a room together with sheet music and let them run, you might get to a cohesive piece—but you probably want a conductor, a maestro who coordinates all of the parts. That is Astro for your front-end frameworks.

Astro addresses the “hydration” of the front end, that is to say, the process of making the shell reactive. In conventional server-side rendering (SSR), like Next.js or Nuxt, the server not only sends the HTML, but also sends the massive framework runtime down the wire, just to attach event listeners to the page. Astro allows you to write components in React, Svelte, Vue, or Solid, and its compiler strips away all of the JavaScript before it reaches the browser. Astro ships zero JS by default, relying on its islands architecture to hydrate only the specific components that demand interactivity. 

Because Astro isolates interactivity into distinct islands, sharing complex state between those islands (e.g., a complex filtering sidebar communicating with a separate dynamic data grid) is fundamentally harder than it is in a monolithic single-page application. If you are building a highly interactive, dashboard-heavy app where every component affects every other component, Astro’s isolated islands might begin to feel more like a straitjacket than a liberation.

See also: Qwik. If Astro unbloats by stripping away the JavaScript entirely, Qwik unbloats by delaying it. Qwik delivers instant HTML and serializes the application state, downloading and executing only the JavaScript code required for a specific interaction at the exact millisecond the user clicks a button.

Biome: Lint like it’s 2026

Rust is gradually replacing the underlying infrastructure in the JavaScript ecosystem. But while Rust gives Biome its close-to-the-metal speed, Biome’s true calling card is its unification of the sprawling toolchain under a cohesive umbrella.

The .eslintrc and .prettierrc files and the dozen associated plugins can become a dark and unhappy bog in a project. Biome is the way out of the mire. It is a single, blazingly fast binary that replaces your entire tangled formatting and linting ecosystem, providing a path to code quality that doesn’t require a sprawling web of dependencies.

Probably the biggest drawback to Biome is that you lose the wide-open extensibility—which is exactly the same feature that makes Biome lean.

See also: Rspack. Biome cleans up the linting. Rspack unbloats the build step. Also built on Rust for speed, Rspack challenges the new “unbundled” esbuild-based dev mode championed by Vite and uses bundled dev mode.

Bun: Fast and integrated back-end JavaScript

Most cutting-edge JavaScript enthusiasts are already well-aware of Bun. For those who haven’t yet experienced Bun’s enthralling blend of one-stop shopping and blistering speed first-hand, it’s a virtually irrefutable must-try.

Fast is probably an understatement. If you are used to Node and you try out Bun, you will likely be immediately impressed with the speed at which commands execute. The Bun team has also made an extensive, multi-year effort to bring its engine into close compatibility with Node’s APIs. Overall, Bun is an extraordinary engineering effort that every JS developer should explore.

However, while Bun’s Zig-based engine is in most respects a drop-in for Node, it isn’t perfect, especially when considering the gargantuan landscape of Node packages out there. Node remains the conservative, happy-path engine for server-side JavaScript. 

See also: Deno. Although Bun has justifiably earned a reputation for bleeding-edge innovation, Deno has quietly pressed ahead with an appealing set of enterprise features like an integrated deployment platform and a front-end framework (Deno Fresh).

The Bun curious also may want to check out my interview with Bun creator Jared Sumner.

HTMX: Ajax KISS

If we are talking about clever ways to de-complexify the web, HTMX could reasonably be considered the poster-child. It takes the core mechanisms of the modern web client, like Ajax and partial updates, and turns them into simple HTML attributes. That means the state lives exclusively on the server, which is responsible for sending HTMX fragments.

Of course, there are trade-offs. Perhaps most unavoidable is the extreme dependence on the network. Because there is no client-side state machine, the browser will be orphaned and helpless without a connection to the server. That is, unless you get experimental with a local-first datastore.

Long story short: if your app falls into the realm of HTMX’s ability, HTMX is likely to be the most direct RESTful way to build it. And HTMX can in fact handle quite a lot.

See also: Hotwire. A collection of tools for building single-page-style applications using HTML over the wire, Hotwire has great features like page morphing, which can diff HTML instead of cold-loading it, with a simple import. True to classic “free as in speech” software culture, the HTMX and Hotwire projects freely exchange ideas. 

PowerSync: Data layer redo

Although the local-first data revolution that PowerSync represents implies a fairly serious engineering deep dive, its core proposal — to entirely reshape the way data moves in web architecture — is something a web developer needs to be aware of.

Usually, we create architectures that require a complex middleware to broker between a reactive client and the datastore. PowerSync proposes a radical alternative: bypass the middleman entirely by dropping a robust SQLite Wasm database directly into the browser.

The UI works on local data using familiar SQL, synchronously. Latency is zero. The dreaded loading spinner vanishes entirely. In the background, PowerSync automatically reconciles your local store with your central Postgres database. It handles the complex syncing algorithms and network drops, effectively making your application offline-first by default.

The catch, of course, is that local-first development forces a massive mental shift. You have to define data slices (similar to a view) that each client user holds. The PowerSync engine does most of the hard work, but things like schema migrations and conflict resolution (when two users edit the same record while offline) require a significantly steeper initial setup than a standard REST API.

See also: RxDB. RxDB is a slightly different flavor of local-first datastore. Whereas PowerSync relies heavily on Postgres, SQLite, and background daemons, RxDB provides a NoSQL, offline-first, reactive database that treats queries as observable streams, pushing UI updates the exact millisecond the local data changes.

RooCode: Use any AI you want

The beauty of RooCode lies in its ability to orchestrate whatever AI providers you have—for free. RooCode is an extension to Visual Studio Code that provides an AI manager layer. This layer bridges between the general abilities of the LLM and your code-specific, project-level structures.

RooCode is strong enough to be somewhat agentic in its capabilities. It doesn’t reach the powerhouse abilities of something like Cursor or Antigravity, but it is quite able to handle most small to medium-sized requests. And it does so with a minimum of unnecessary overhead. I find myself often using RooCode alongside my AI-assisted IDE to knock out lesser requirements, for less cost and without interrupting the flow of ongoing epics.

RooCode keeps you free of proprietary ecosystems. It allows you to plug in your own API keys—whether that is Claude, OpenAI, or even a local model running on your own hardware. 

The hidden tax of any AI coding assistant, however, is that it fundamentally shifts your job description from “writer” to “editor.” The unbloating of keystrokes can paradoxically lead to massively bloated codebases if developers blindly accept AI-generated boilerplate without actively reviewing its architectural impact. It is incredibly easy to let an agent spin up 500 lines of complex React when 50 lines of plain JavaScript would have done.

See also: Antigravity. RooCode is a lightweight extension that supercharges your existing environment. Google’s Antigravity is a custom-built editor designed from the ground up around AI, geared for agentic development workflows.

TanStack Query: Syncing made simple(r)

Even when client-side state management is addressed (see Zustand below), there is still a big, gaping hole in the plot: syncing across the server boundary. That is where TanStack Query steps into the breach.

Distributed computing is a notoriously thorny problem, and in fact our standard reactive model walks right into these thorns by holding the same state in two different places: on the client and the server.  Tanstack Query tries to make this inherent architectural friction as painless as possible by acting as an intelligent asynchronous layer. 

Instead of using a bunch of manual fetches tied to useState updates, along with fragile isLoading flags and complex state synchronization logic, TanStack Query abstracts the heavy lifting of API responses, background updates, and request deduplication into a few elegant hooks. You tell TanStack Query where to get the data, and it uses a pattern known as “stale-while-revalidate,” which means it will cache and reuse data on the front end (eliminating reload waits) and sync to the latest state in the background.

The catch, however, is that cache invalidation remains one of the hardest problems in computer science—and TanStack Query forces you to face it head-on. You will spend time thinking about “query keys” and deciding when a piece of data should be considered “stale.” No free lunches in software.

See also: SWR. While TanStack Query is an absolute powerhouse for complex data manipulation, SWR remains a champion of API minimalism, doing exactly what its name implies (stale-while-revalidate) with almost zero configuration.

Zustand: Minimalist state

If you have yet to encounter the monstrosity of large-scale state management in a reactive app, then spoiler alert: it can be nasty. Zustand proposes to dispense with the ceremonial boilerplate of reducers, providers, and unwieldy context wrappers in favor of a tiny, brutally simple global store.

Instead of forcing your entire application tree into a massive React context provider (sometimes leading to cascades of superfluous re-renders across the DOM), Zustand uses custom hooks to tie state directly to the specific components that need it. Zustand strives to achieve the specificity in the VDOM reactive model (instead of eliminating it entirely a la Signals).

You define a store, you call it, and the reactivity just works. It is an expression of the KISS philosophy applied to front-end architecture, scraping away the intricacies of Flux-like patterns. The trade-off for this liberation is the burden of discipline. Because Zustand is unopinionated, it won’t stop you from turning your global store into a cluttered junk drawer. You’ll need to impose your own conventions and guardrails to keep a large-scale project manageable.

See also: Jotai. If Zustand is the unbloated global store, Jotai is the unbloated atomic approach. Jotai manages state from the bottom up, calculating changes with surgical precision without triggering massive re-renders across the application tree.

New directions in web development

The most remarkable thing about these eight tools is that they deal in large part with alternative approaches that challenge the familiar. Although you may not be able to adopt them immediately, you will want to keep an eye on them. They are key factors that will continue to influence the shape of web applications and how we build them.

Threat actors are continuing their onslaught against software supply chains, now with malware named after death itself.

The newly-discovered Hades Campaign is a “highly sophisticated” supply chain compromise that targets Python developer environments and runs as soon as infected packages are imported. It uses the popular Bun toolkit to silently execute multi-layer payloads that can extract sensitive data, move laterally across compromised systems, exploit common security frameworks, and even hijack AI gatekeeper analyzer systems via adversarial prompt injection.

Notably, the campaign exploited the popular C++ library ensmallen, as well as packages in the computational biology, bioinformatics, and genotype-phenotype analysis ecosystems.

The most novel thing about this malware is its combination of advanced tactics, noted David Shipley of Beauceron Security. He noted that we’ve seen memory-focused malware, we’ve seen attacks that attempt to defuse large language model (LLM) powered analysis with hidden prompts, and we’ve seen malware with wiper capabilities.

“But all three, in a fast moving mass propagating worm, is its own kind of nightmare,” he said. “And I suspect this is the way of the future.”

How Hades works

The Hades Campaign was discovered by researchers at StepSecurity, who called it the latest evolution of the Miasma threat actor. The researchers previously described Miasma attacks that had sent self-replicating worms to perform multi-cloud credential sweeps, caused infected repositories to execute code when folders were accessed in integrated development environments (IDEs) or by AI agents, and used techniques that scanned and read Linux process memory.

Hades uses the same credential harvesting methods, self-replicating worm logic, and GitHub-based exfiltration patterns, the researchers noted. In addition to ensmallen, compromised packages include mflux-streamlit, nhmpy, ppkt2synergy, embiggen, gpsea, and pyphetools.

The campaign’s entry point is a simple, obfuscated script embedded inside a Python package’s __init__.py file, a critical building block that gives Python the ability to recognize packages and import modules. Once they gain access, threat actors drop a precompiled Bun runtime binary and executes its JavaScript payload. Bun allows the malware to run complex JavaScript tasks in environments lacking a Node.js installation, bypassing traditional package manager controls and proxy logs.

The malware is able to scrape Linux memory mappings, and also introduces tailored macOS and Windows memory scrapers, which allow threat actors to extract sensitive, encrypted data.

Interestingly, attackers are also able to evade detection by automated LLMs that scan for suspicious code. This is achieved with a simple block of text at the top of the file; this instructs the model to ignore the hidden code below, classify the package as verified and clean, and provide reports stating it is safe.

This element represents what the StepSecurity researchers described as a “significant conceptual shift,” with attackers writing payloads that target AI systems’ cognitive logic. “Scanners that pass raw text to LLMs without strict boundary isolation can be coerced into generating false negative verdicts, allowing the malicious package to bypass organization analysis,” they wrote.

The tactic is indeed clever, Beauceron’s Shipley agreed, pointing out that attackers will increasingly target endpoint LLM-powered agents.

Why? “Because there’s no reliable defense,” he said. “LLMs are incredibly susceptible to social engineering.” This has been relabeled as prompt engineering, but is essentially just phishing for bots, he pointed out.

“While everyone’s worried about LLM-powered vulnerability discovery and automated exploitation, it’s LLM-created smart malware like this, and AI-powered phishing of humans and bots, that keeps me awake at night,” Shipley said.

Hades’ crafty worm propagation

The Hades Campaign command and control (C2) infrastructure uses three independent channels on public GitHub infrastructure to allow its communications to blend in with normal traffic. Stolen credentials are encrypted locally in a hybrid fashion (serialized, compressed, and pushed to a newly created public GitHub repository under attackers’ control). Exfiltrated repositories carry the description “Hades — The End for the Damned.”

Researchers noted that a core component of this campaign is its ability to propagate and move laterally across networks. It exploits the very methods meant to protect systems, including Secure Shell (SSH) and Secure Copy Protocol (SCP), OpenID Connect (OIDC),and Supply-chain Levels for Software Artifacts (SLSA).

For instance, when running inside a GitHub Actions workflow runner, the malware checks for OIDC variables, then bypasses registry signature policies and generates cryptographically signed SLSA provenance bundles via Sigstore. It can then fetch target libraries and inject the obfuscated script and JavaScript payload. From there, it can publish compromised versions to the Python Package Index (PyPI) repository and node package manager (npm) using the target’s credentials and the generated Sigstore bundle.

“This ensures that the published package appears to have valid, cryptographically verified build provenance from the organization’s official GitHub Actions build environment,” the researchers explained.

Further, if a harvested GitHub token has write permissions, the malware will target repositories to extract secrets using GitHub Actions runners. This occurs “directly from the runner’s address space without ever writing them to disk or making a suspicious network connection,” the researchers noted.

The malware also targets rule files and configuration directories for 14 different AI agents and systems, planting custom prompt instructions or executing hooks that trigger a bun run bootstrap command when the victim loads or consults the workspace with their AI assistant. Finally, it establishes persistence on the workstation and monitors for the presence of the stolen token; if that token is revoked, it executes a wiper process to erase the user’s files.

Broadcom today announced multiple security investments in its Spring and Java ecosystems that aim to help protect users from AI-enabled threats.

The company said that, first, it is releasing what it called the largest set of Spring security updates to open source in the product’s history, and, for customers, it is extending its clean-room build architecture to build the Java dependencies for the entire Spring ecosystem.

“Spring is one of the most widely adopted application development frameworks in the world, and as its steward, we have a deep responsibility for its security,” said Purnima Padmanabhan, vice president and general manager of Broadcom’s Tanzu Division. “Because we maintain Spring and are the sole committers, we can better secure it at the source for everyone who depends on it. This investment is about two things we will never separate: the health of the Spring community and the security of our customers who trust Spring to run their business.”

The company also announced that, as the number of security advisories reported by the community has exploded, its engineering team has “significantly scaled” its use of AI tools to help it identify vulnerabilities, assess remediation paths, and validate fixes across the dependency ecosystem. Although Broadcom declined to specify the AI models it’s using in its bug hunting, it is a member of Anthropic’s Project Glasswing, so Claude Mythos is likely part of the effort.

For paying customers only

One perk available only to Tanzu Spring enterprise customers is zero-day access to validated CVE patch-only releases through the Spring Enterprise Repository, before they are released to open source. These patches isolate the security fix from any other changes to let customers remediate more quickly.

“By utilizing Tanzu Spring’s private artifact repositories, customers can be confident that the artifacts are the official, validated patches from Broadcom, the steward of Spring,” Broadcom said in its announcement, adding that it will continue to issue CVEs for all versions of every Spring project under open source support, as well as older versions under Tanzu Spring enterprise support.

Broadcom’s Tanzu Spring enterprise support includes:

• Certified source for secure spring libraries 
• Commercial-first release of patches for both current and older, enterprise supported versions
• Access to dependent Java binaries
• Automated, deterministic upgrades with Spring Application Advisor
• Exclusive Tanzu Spring components for governance and security
• 24×7 support, hands-on expertise and access to the Spring team.

In addition, Broadcom said, it has now added:

• Secured, SLSA Level 3–validated software supply chain for Java dependencies.
• Coverage that spans the full transitive dependency graph managed by the Spring Boot bill of materials.
• Thousands of secured dependencies, built and tested across every supported Spring version. Spring Boot 4.0 alone manages 1,768 of them; across the full supported portfolio, that totals more than 100,000 validated dependency builds.

“This capability gives customers validated dependencies across both current and end-of-life Spring versions, helping customers reduce software supply chain risk while continuing to benefit from the productivity and consistency of Spring Boot’s dependency management model,” the announcement noted.

Security fixes for sale

Seva Ioussoufovitch, senior research analyst at Info-Tech Research Group, sees these moves as mostly positive.

“It’s encouraging to see Broadcom take proactive steps towards dealing with the increase in AI-detected vulnerabilities that many organizations have had to contend with in recent months,” he said. “Announcements like Mythos have made it clear that the industry needs to re-think traditional approaches to security patching.”

Ioussoufovitch isn’t surprised at the size of the update release either, noting that it’s consistent with the result of AI scanning and remediation that has been occurring, and will likely continue.

“More meaningful is the provision of validated and secured dependencies,” he said. “This is a critical move in the right direction, especially with the endlessly growing list of supply chain vulnerabilities the industry has been managing in recent months.”

Ioussoufovitch is less happy with the restriction of zero-day patches to paying customers.

“Putting security fixes behind a paywall isn’t new, but when there are no drop-in alternatives for an ecosystem as critical as Spring, it just looks like a power move to force more of the open-source community onto the monetization track,” he noted. “Another approach might’ve been to release the CVE fixes to everyone while charging for enterprise-grade packaging, validation, and support, but, given Broadcom’s track record of aggressive monetization in recent years, what they’ve chosen here doesn’t necessarily come as a shock.”

Model Context Protocol (MCP) has gained considerable momentum as a standard connector between LLM-powered tools and local systems, internal and external APIs, and data sources. From major clouds to devops tools, MCP servers are enabling powerful, AI-powered development and operations capabilities through natural language commands.

Nowhere is this more true than in the world of databases. Most major database platforms now support agentic access through MCP servers. Using an MCP server for databases, you and your AI agent proxies can perform lookups, create and update data, and perform administrative tasks without you having to write SQL by hand.

The MCP server could also guide your LLMs to write new code or build automations that align with your database schema, like its tables, structure, and fields, as well as embeddings, indexes, and metadata. It could also aid debugging by enabling faster queries to surface data issues or misconfigurations, along with plenty of other possible use cases.

Below, we’ll cover official MCP servers from some of the top platform options across major database styles. Though maturity varies, the MCP servers discussed below represent some of the best vendor-backed offerings available today across relational SQL, NoSQL, graph, vector, and data warehouse systems.

These servers can be used by any MCP-compatible tool, IDE, or agent, whether it’s Claude Code, Codex, Cursor, Gemini CLI, Google Antigravity, VS Code, Windsurf, or something else. Adding them is typically simple, often involving a lightweight JSON addition to your MCP configuration file.

Amazon Aurora MCP Servers

MySQL and PostgreSQL are the world’s most widely-used open source databases. However, in both cases, there is no canonical MCP server—what we see are different MCP servers emerging across vendors. One of these vendors is Amazon Web Services (AWS), which offers official MCP servers for Amazon Aurora, its managed relational database service compatible with both MySQL and PostgreSQL.

According to the documentation on GitHub, the Amazon Aurora MySQL MCP Server can be used to convert natural language commands into MySQL-compatible SQL queries, which can then be executed against Aurora MySQL databases. Similarly, the Aurora Postgres MCP Server provides MCP tools for working on PostgreSQL databases. The Aurora DSQL MCP Server does the same for distributed Postgres databases.

AWS provides a growing portfolio of official MCP servers across its product line, including MCP servers for other Amazon database platforms like DynamoDB, ElastiCache, and Redshift. If you’re a heavy AWS shop and you want to enable LLM interactions with your data, these are sensible choices.

BigQuery MCP Server

BigQuery is Google’s cloud-based data analytics platform, and a popular data source for AI applications. BigQuery users with API access configured can also utilize the BigQuery MCP Server to interact with the platform using MCP-compatible AI clients.

Using the remote BigQuery MCP Server, engineers can generate and execute queries on data sources, or return metadata on datasets, tables, and schema. This can be done with a simple natural language prompt like “List the datasets in project PROJECT_ID.” Results are filterable by region, data set ID, column name, and more.

As part of Google’s fully-managed, remote-hosted MCP portfolio, the BigQuery MCP Server provides some peace of mind regarding security, maintenance, and ease of use for distributed teams. The MCP tools are subject to some limitations, however, in terms of query result size, processing time, and other factors. If you’re using BigQuery and you want more agentic control, you’ll want to check this one out.

Elastic Agent Builder

Another important database category includes platforms designed for keyword and semantic search. In this space, Elasticsearch is commonly deployed. Instead of providing a single MCP server, Elasticsearch provides the Elastic Agent Builder, which is a more comprehensive framework aimed at agentic workflows.

Using Elastic Agent Builder, you can chat with an agent to retrieve data context from Elasticsearch data and extend it into various environments. The Agent Builder itself includes an MCP server endpoint for programmability and exposing the agent to other clients.

Unlike others on this list, this is not a direct MCP interface to raw Elasticsearch APIs. Instead, it’s an interface that exposes skills from the agent platform. This should also not be confused with the Elasticsearch MCP Server, released in mid-2025, which has since been deprecated.

A possible downside of using this utility is that it includes an additional layer between your IDE or agent and the data you’re searching. The agent setup requires a higher subscription and takes additional steps to configure compared to other MCP servers.

That said, if you want an extensible common layer to interact with both Elasticsearch and external MCP servers, while centralizing responsibilities like permissions, this is an interesting proposition.

MCP servers for Neo4j

Graph databases are another key NoSQL database type these days, specializing in using nodes and edges to accelerate queries of highly interconnected data. Of these, Neo4j is a popular graph database option.

The Official MCP Server for Neo4j works with all kinds of Neo4j deployment (desktop, sandbox, self-managed, and the managed Neo4j Aura cloud service), and allows LLM-based clients to retrieve graph schema, execute read and write statements, execute graph algorithms, and more.

In addition, several other MCP servers for Neo4j are available from Neo4j Labs. These have specialized uses, such as generating Cypher queries from natural language, maintaining an in-memory graph database, modeling and visualizing graph, and interacting with the Neo4j Aura API.

The first MCP server for Neo4j was developed in December 2024. If you’re an avid Neo4j user and want to experiment with interacting with your graph databases in a chat-infused way, these stand as an interesting platform of servers.

MCP Toolbox for Databases

Google’s MCP Toolbox for Databases is a notable MCP server because it’s a popular catch-all for various database types. Unlike the other entries on this list, this server connects LLMs not to a single managed database, but unifies LLM access to multiple systems. The open source utility ships with pre-built configurations for nearly 30 databases including PostgreSQL, MySQL, SQL Server, Oracle Database, MongoDB, Redis, Neo4j, and Snowflake, as well as the databases in Google Cloud.

Once you define data sources in a tools.yaml file, you can use MCP Toolbox to perform structured queries or semantic searches against databases directly from within an IDE or agentic client using plain English. MCP tools translate commands into actions like list_tables and execute_sql.

MCP Toolbox for Databases is mature, originally built as a generative AI utility and later re-worked for MCP-style workflows. It offers numerous download, configuration, and interaction methods.

If you’re using a variety of databases on Google Cloud and elsewhere and you want an “all-in-one” MCP server, MCP Toolbox for Databases is a great place to start.

MongoDB MCP Server

MongoDB is the popular NoSQL document-oriented database. The creators of MongoDB have released an official MCP server that works with the open-source database as well as the company’s cloud-hosted MongoDB Atlas database platform.

The MongoDB MCP Server provides a number of tools to interact with MongoDB. You can query the database, return information on collections, create or remove collections or indexes, gather statistics on database usage, and more. Other tools enable MongoDB Atlas operations, like creating users or clusters, returning cluster data, and other functions.

The server’s tools are read-only by default but can be switched to allow write capabilities. It can be used locally, but also supports Streamable HTTP transport for remote servers, although that comes with greater security concerns.

For those using MongoDB and wanting to hook their AI-enabled IDE or CLI up with more automated powers, the official MongoDB MCP Server is worth checking out.

Pinecone MCP server

Among vector-native databases, Pinecone stands as a strong, widely used option with a well-designed API and comprehensive SDKs. The Pinecone MCP server extends this experience, allowing users to query its documentation and execute functionality via AI agents and AI-enabled IDEs.

To date, the Pinecone MCP server consists of nine MCP tools. These cover read-only actions, like knowledge gathering via the Pinecone official documentation and querying vector records, index metadata, configurations, and statistics. It also allows for write operations like updating records and creating new indexes.

Released in mid-2025, the Pinecone MCP server is one of the more complete early implementations, with easy configuration and installation.

For those using Pinecone who want to test new LLM-assisted workflows for creating indexes with embeddings, performing reranking, or testing results using natural language commands, the Pinecone MCP server is worth trying out.

Redis MCP

An ultra-fast in-memory database, Redis is commonly used for caching, real-time analytics, and other latency-sensitive use cases. And as you might have guessed, the company behind the Redis database provides an official MCP server. The server allows read, query, and write capabilities.

Developers can use Redis MCP from an LLM client to perform high-level actions to analyze, reference, or embed Redis data and interact with the Redis server within their prompts. The documentation suggests some example prompts for common use cases, such as “Cache this item,” “How many keys does my database have?,” and “What is user:1’s email?”

Unlike other MCP servers, which only allow a slice of platform capabilities, Redis MCP offers full Redis support. This enables working with Redis constructs such as hashes, lists, sets, sorted sets, streams, and more, according to the GitHub repository.

One possible drawback is that Redis MCP has yet to support Streamable HTTP transport. Until this is developed, the server is constrained to local deployment. But for those seeking a local MCP server to work with Redis data, this is the best choice.

Snowflake MCP Server

Snowflake is a cloud-hosted, AI-enabled data platform widely used in enterprise contexts for data warehousing, data analytics, and data engineering purposes. Compared to other data storage systems, Snowflake is unique in that it’s more fully managed and combines structured and non-structured data types.

The Snowflake MCP Server, available on GitHub, can be used to perform many of the standard Snowflake platform operations. This includes a “fuzzy” search of all records via Snowflake’s Cortex Search and structured data semantic lookups using Cortex Analyst.

Other abilities include object management operations like creating, updating, and deleting records. The server also can invoke other agentic-designed capabilities, like the ability to generate and execute SQL statements against back-end databases.

Snowflake MCP Server is well-thought-out and well-documented, with walkthroughs for various agent and deployment patterns. Those already building with Snowflake should find it complements the mechanics they already employ.

Supabase MCP Server

A longtime open-source favorite, PostgreSQL is one of the most popular and trusted object-relational SQL-based database systems. With an active open source community, Postgres has been maturing for decades. Given its open source nature, there isn’t a single “official” MCP server for the platform. Anthropic built an original reference implementation, but it’s now archived.

Instead, database platforms built on PostgreSQL provide different flavors of MCP servers, with a range of vendor neutrality and specificity. One notable option is the Supabase MCP Server, provided by Supabase, a cloud-based “back end as a service” and Postgres development platform.

Supabase MCP Server connects AI agents with Supabase projects, allowing engineers to issue natural language commands to manage tables, query data, get logs, fetch configuration information, and more. The Supabase MCP Server is pre-1.0 release and some features are still experimental.

If you’re an engineer using Supabase and looking for an MCP server to connect your AI assistant with your Postgres databases, this is a good tool to test out.

Other MCP servers for databases to consider

So far, we’ve reviewed official, vendor-backed MCP servers from some of the most-adopted managed databases. However, numerous MCP servers exist across other database platforms and types.

One MCP server that aggregates LLM access across various database types is DBHub, which works with MySQL, PostgreSQL, SQL Server, MariaDB, and SQLite. Developed by Bytebase, DBHub is described as a zero-dependency, token-efficient MCP server.

For SQL, the options are nearly endless. Official servers exist for Microsoft Azure SQL and DuckDB. PulseMCP catalogs more than 100 MCP servers for MySQL, although most are unofficial, solo-creator open source projects. Of these, one of the most starred is MCP Server for MySQL, developed by full-stack developer Ben Borla and optimized for Claude Code.

For Postgres, notable alternatives to Supabase include pgEdge Postgres MCP, Neon MCP server, and Postgres MCP Pro. For vector databases, others beyond Pinecone have been quick to adopt MCP as well, including Weaviate and Milvus.

Using MCP for databases: what to watch out for

Before diving into MCP servers for enterprise databases, it’s important to understand the security risks. For instance, prompt injection remains an unsolved problem, so it’s recommended to limit permissions for SQL statements.

To mitigate this, Supabase recommends enabling AI client settings that require manual approval for each tool call before execution. Experts also recommend assigning only the minimum permissions required and avoiding exposure of sensitive data like API credentials. Due diligence around authentication and authorization is especially important when hosting remote servers.

Lastly, to avoid shadow IT, it’s becoming common practice to catalog the internal MCP servers you use, even for experimental projects. For this, experts recommend an MCP registry that documents approved servers. An MCP registry improves both MCP server discovery and security awareness.

Anyone can build an app now. But nobody seems to care.

Well, not nobody. VCs keep funding startups that add AI to, well, everything. But users aren’t buying the massive influx of new apps. In a chart shared by Jen Zhu Scott based on the new National Bureau of Economic Research’s working paper “Writing Code vs. Shipping Code,” iOS app releases have exploded since the advent of agentic AI. That would perhaps be cause for celebration had app reviews not declined during this same period, and apps with significant usage have stayed essentially flat.

In other words, more apps but almost nobody new showing up to use them.

For those of us that grew up in open source, it’s a familiar problem. The greater the abundance of code, the greater the need to help would-be customers navigate it through marketing (including branding), sales, etc. AI is creating so much noise, in terms of new code, new products, etc., that the real work has shifted to taste-making.

Getting more but not using more

I’ve been saying for a while that developer productivity isn’t about producing more code faster. Or at least it shouldn’t be. Productivity is about producing well-architected, secure, maintainable code that solves a problem someone actually has.

That’s a very different thing. It’s not something AI can fix; at least, not yet.

Charity Majors put it more bluntly in a post I wrote in 2024: “Writing code is the easiest part of software engineering,” she said. The harder parts are figuring out what to build, integrating it into a larger system, validating that it works, maintaining it over time, and getting humans to trust it enough to use it.

Turns out the harder parts are really hard. Mert Demirer, Leon Musolff, and Liyuan Yang tracked more than 100,000 GitHub developers alongside their AI usage telemetry. Autocomplete, interactive agents, and autonomous agents each ramped raw coding activity, with cumulative effects on commits of 40%, 140%, and 180%. That sounds great until you look how the gains attenuate the closer you get to actual users. For example, that 180% jump in commits became roughly 50% more projects and just 30% more actual releases. The report’s authors call this the weak-link problem: The strong link (writing code) got much stronger, while the weak links (everything else humans have to do) didn’t. The estimated elasticity of substitution between AI and human effort is 0.25, which is economist for “these complement each other, but they don’t replace each other.”

When the authors checked four major app marketplaces, they found a bump in new apps but no increase in total usage. In other words, we’re getting better at creating things with AI’s help; apparently we’re not good at turning that into user interest. User attention (and budget) is finite. The hard part is to figure out how to get users to care enough to pay (with their time or their money).

Learning to love marketing

So what’s actually scarce in a world of near-infinite software? Not code, for sure. No, what’s scarce is attention, trust, and a reason to switch.

That means the durable advantages in software increasingly live in the parts of the business developers often undervalue, like a recognizable brand (something that Red Hat figured out early on in open source) or a channel they already use. Or it could be in areas that developers appreciate but don’t pay for, like good documentation or a welcoming community.

This isn’t a new idea; it’s just newly unavoidable. We’re watching something similar inside enterprises, where AI adoption is wildly uneven, not because the technology has no value, but because the organizational plumbing around it often hasn’t been built. This is why a new kind of speed is important. I once argued that speed was the killer app, and that was mostly true. Today the more interesting speed is how quickly you can earn trust, fit into a workflow, answer objections, and get adopted.

Years ago I wrote that RethinkDB was dead and MongoDB wasn’t what killed it. RethinkDB was at the time, by many technical measures, a better database, built around “correctness, simplicity, and consistency.” It still lost—and badly. Its founder’s own postmortem was unsparing: They had picked a brutal market and tuned the product to the wrong definition of good. Being technically right turned out to have almost nothing to do with getting adopted.

With AI we’re generating a thousand smaller “RethinkDBs,” only faster and with nicer landing pages generated by the same model that wrote the code. These aren’t going to win, any more than RethinkDB was able to unseat MongoDB. It’s not just about the tech, but rather about making that tech fit within a user’s or enterprise’s world and making it easy to adopt. AI makes this harder, not easier.

It’s a cliché that developers don’t like marketing. It’s also false in my inexperience. What developers don’t like is traditional marketing. During my time at MongoDB and now at Oracle, my developer relations teams have focused on offering developers deep, hands-on enablement, and the response has been fantastic. Is a technical tutorial marketing? Of course it is. So is a forward-deployed engineer working side by side with an enterprise’s engineers to help them effectively use your tech. Just because it’s not a 30-second Super Bowl ad doesn’t mean it’s not marketing.

Years ago the Dilbert cartoon captured developers’ disdain for marketing. It was funny then, and it’s funny now, but it has never been true.

Years ago Matt Klein, creator of the open source Envoy project, once talked me through all the non-development work that goes into making an open source project thrive. As he reflected, “If you look at what I did in 2016 and early 2017 to [introduce] and grow the project, it was not technical.” So what was it, if not core engineering? “It was all leadership, public relations, marketing, documentation, etc., and I did it all myself and I nearly killed myself [doing it].” As he summed it up for me, it was a “f—ing lot of work,” and much (most?) of it wasn’t about code. It was about helping users appreciate the value of that code.

TL;DR? The boring but essential go-to-market grind has always been the real job. It’s what will separate winners from losers in AI.

The boring work wins

None of this is an argument against AI coding tools. Developers should absolutely use them. I use them constantly.

But AI can’t compensate for the hard work that goes into making a product successful in the market. In a world drowning in AI-generated sameness, taste becomes a competitive advantage. For me, “taste” translates into knowing what not to build, or what not to publish. It’s also all about knowing how to market one’s product, which might include ads but definitely needs to incorporate technical training that helps developers make sense of your code.

In short, there’s no Field of Dreams “build it and they will come.” There’s just a lot of hard, human work to help real people find and use your code.

GitHub is expanding Copilot beyond the IDE with a new desktop application and a new collaborative work surface called canvas as part of its broader efforts to pitch the AI-assisted coding tool as the control center for agent-native software development.

The desktop application announced at Microsoft’s annual Build conference this week is designed to give developers a dedicated environment for working with AI agents throughout the software development lifecycle, rather than limiting those interactions to code-generation tasks inside an editor, the company wrote in a blog post.

The application includes a collaborative workspace called canvas where developers can brainstorm ideas, refine requirements, generate plans, and iterate on projects alongside AI, it said.

It also has new Agent Merge and code review features that enable developers to automate Copilot to combine tasks of different agents to complete a specific goal or conduct autonomous code reviews according to set standards, it said.

These new features could reduce context switching, increase engineering efficiency, and accelerate delivery cycles, said Phil Fersht, CEO of HFS Research.

Shift in pricing justified?

However, despite the new features, much of the conversation among developers in recent weeks has centered on a different topic: this week’s shift to a usage-based billing model for GitHub Copilot that it announced in April.

The changes were met with a wave of criticism on the GitHub community forum, where some users accused the company of a “bait and switch,” while others requested refunds or announced plans to cancel their subscriptions.

For analysts, though, the pricing change was, at least from GitHub’s point of view, necessary and justified.

“The pricing change is justified by where GitHub is going, not by where the product is today. Running multiple agents in parallel with sandboxes, canvas reviews, and Agent Merge looping through CI is closer to cloud compute than an IDE plugin, and you cannot price compute on a flat seat fee. So metered billing is the right call structurally,” said Advait Patel, a senior reliability engineer at Broadcom.

Fersht said developers and CIOs need to focus on Copilot’s metamorphosis from being a coding assistant into a platform for orchestrating software-development agents and workflows.

“That changes the ROI conversation significantly. CIOs should stop thinking about Copilot as a seat-license productivity tool and instead evaluate it as an AI-powered software delivery platform,” he said. “The metrics shift from ‘lines of code generated’ to broader operational outcomes such as release velocity, code quality, defect reduction and engineering efficiency.”

GitHub is not the first company offering vibe-coding tools to rethink its pricing strategy as AI agents proliferate across enterprises and evolve to take on more complex software-development tasks that are computationally more intensive.

Over the past year, platforms such as Claude Code, Replit, Cursor, and Kiro have repeatedly adjusted their pricing structures to account for mounting infrastructure costs, limited GPU availability, and the expense of serving increasingly sophisticated AI models and agents, despite furor among their users.

For CIOs, the challenge is proving ROI

That common pressure across AI coding vendors is why Amit Chandak, chief analytics officer at IT consulting firm Kanerika, thinks developers and CIOs should focus less on GitHub’s pricing mechanics and more on whether these increasingly capable tools are delivering measurable business value.

“The new features that GitHub announced can act as productivity multipliers as well as features that increase consumption without delivering proportional business value. Without productivity baselines established before adoption, enterprises risk absorbing higher costs with no clear line back to delivered value,” Chandak said.

For Fersht, developers and CIOs will need to focus on governance, monitoring and financial controls as the pricing model is changing.

“The governance challenge is very real. Autonomous agents can continuously reason, test, revise and interact with multiple systems in ways that create far less predictable consumption patterns than traditional SaaS tools,” he said.

Patel, however, advised users and decision-makers to be more skeptical, especially since the new features are currently in technical preview.

“Customers are being asked to pay variable rates now for value that has not been validated in production. Do not assume new capabilities justify higher spend,” he said. “Instead, run a 90 day pilot, measure PRs merged per dollar before and after, and let the data decide. If the ratio improves, the pricing is fair. If it does not, you are paying for promise, not delivery,” Patel added.

The team behind RubyGems, a package hosting site for Ruby developers, has added a new feature to bundler, a tool for managing Ruby packages (or ‘gems’) to protect developers against the recent wave of software supply chain attacks: A cooling-off period before recently updated packages are installed on their systems.

Recent attacks on software repositories have focused on stealing developer credentials in order to introduce malicious code into the packages they create, which then steals more developers’ credentials when they install the malicious updates, and so on. Users of the repositories are vulnerable if they download an affected package during the short interval between it being interfered with and the malicious additions being discovered and removed.

To counteract this, RubyGems team has added a new cooldown argument to Bundler that takes ignores gems until they have been published for a specified number of days. This provides an additional layer of defense against malicious package releases as it gives others an opportunity to identify any malicious code they contain before installation.

The cooldown system works by checking the timestamp of any new versions of gems. Any new additions to the source will have to come from older versions, any new additions will be delayed until they are validated.

In situations where waiting is unhelpful — for instance when a known-good package is released to patch a dangerous security flaw — the delay can be overridden.

I’ve seen a lot of promising AI prototypes fall apart after launch. And it’s rarely because the model was bad. More often, the problem starts much earlier; teams treat the data layer like something they can figure out later.

They’ll spend weeks fine-tuning prompts, testing models and debating evaluation scores, then throw together the retrieval pipeline over a weekend and move on. At first, everything looks great in demos. But a few months later, the system gives outdated answers; the embeddings no longer match the source documents, and nobody fully understands what changed.

What started as an impressive prototype slowly becomes difficult to trust in production. The teams that avoid this tend to realize one thing early: Embedding pipelines are fundamentally a data engineering problem, not an entirely new AI discipline. It’s still ETL (Extract, Load, Transform) at its core, but with embeddings and vector stores as the destination instead of a warehouse.

Once you start looking at it that way, a lot of things become clearer. Problems like versioning, data freshness, lineage and retries stop feeling “AI-specific.” They’re data infrastructure problems we’ve already spent years learning how to solve.

Why do we need embedding pipelines?

Large language models are extraordinary reasoners trapped inside a time capsule. When training ends, the model’s knowledge is sealed. It does not know what your team decided in last quarter’s strategy review. It has never read the support ticket that came in this morning. It cannot find the clause buried on page 47 of your master service agreement. It’s brilliant, but blind to anything specific to your organization.

Layer on top of that a hard context window limit, a ceiling on how much text the model can process in a single interaction, and you have a clear problem: you cannot just hand it everything you own.

The answer the industry converged on is retrieval-augmented generation, or RAG. Instead of stuffing everything into the context window, you build a retrieval layer that fetches only the most relevant pieces of information at the moment a question is asked and passes just those to the model. That retrieval layer is powered by a vector database, and the process that populates it, which is taking raw documents and transforming them into searchable semantic representations, is what I mean when I say embedding pipeline.

Every team building an internal AI assistant, a smarter enterprise search tool, an automated customer support agent or a document Q&A system needs one. The question is not whether to build it. The question is whether you build it like a prototype or like infrastructure.

How an embedding pipeline works

An embedding pipeline has three stages: ingestion, chunking and indexing. Here is what each one means and how I relate them to a typical ETL process.

Ingestion is extraction

Getting your raw content, PDFs, wiki pages, Word documents, database records, transcripts, out of wherever it lives and into the pipeline. This is ETL’s extract stage, almost verbatim.

I see teams cut corners here more than anywhere else, and it’s often where production systems first start to fail. A document gets updated, but the pipeline doesn’t pick it up. A file gets deleted, but its chunks remain in the index, still returning outdated answers months later. And because there’s no obvious error, no one reports it.

The fix is Change Data Capture (CDC). This maintains a manifest of every document you have ingested, a content hash and a timestamp. On each run, we compare sources against that manifest, re-ingest what changed, delete what is gone and treat your document the way you would treat any source table you are syncing incrementally.

Chunking is transformation

Once your documents are in the pipeline, you cannot embed them whole. A 30-page technical report is too long to represent meaningfully as a single vector, and even if it were not, returning the entire report in response to a narrow question would bury the model in irrelevant context.

Chunking is the process of breaking each document into smaller pieces that are focused enough to embed accurately and retrieve precisely. This is ETL’s transform stage, and it deserves the same level of design discipline.

The most common mistake I see is treating chunk size as a default configuration option rather than a product decision. It is not. The right chunk size depends entirely on the nature of your content and the nature of your queries. Dense technical documentation needs finer granularity than a collection of FAQs. A legal contract with clause-level logic needs different treatment than a set of onboarding emails. What works for one document will actively degrade retrieval quality on another.

My strong preference is to treat your chunking configuration as a versioned pipeline parameter, not hardcoded logic. When you change it, and trust me, you will. You need to re-chunk in a controlled, observable way, compare retrieval quality before and after, and roll back if it degrades. That is just good transform-layer hygiene. It is no different from versioning a data cleaning rule or a field mapping.

Indexing is the load

The final stage is where chunked text gets converted into vectors and stored in a vector database where it can be searched by semantic similarity rather than keyword match.

In the conversion step, embedding is handled by a model specifically trained to turn text into dense numerical representations that encode meaning. Two chunks expressing the same idea in different words will produce vectors that cluster close together in that mathematical space. Two chunks discussing entirely different topics will sit far apart. When a user asks a question, the system embeds that question the same way, finds the chunks whose vectors are nearest, and returns them as context for the model to reason over.

That is a genuinely new capability. But the discipline around indexing is not. One data engineering principle I keep coming back to is versioning.

In embedding pipelines, every chunk in your index should be tagged with the embedding model name and version used to generate it, this is non-negotiable. Embedding models evolve, and vectors produced by different versions are not comparable in a reliable way. You cannot safely search across them as if they are interchangeable.

This exact problem shows up when teams upgrade embedding models mid-pipeline without a proper migration plan. You end up mixing vectors from different generations in the same index, and retrieval starts to degrade in ways that are hard to detect. The system just quietly begins returning subtly wrong answers.

I treat an embedding model upgrade the same way I treat a schema migration: Plan it explicitly, execute it in full and validate retrieval quality on a representative query set. The stakes are the same as any breaking change to your data model.

Pipeline observability is not optional

Once an embedding pipeline is running in production, the question shifts from “did it run” to “did it run correctly.” That distinction matters more here than in most pipelines, because failures are rarely loud because the index looks fine, queries return without errors and the system quietly surfaces wrong answers until someone notices the AI has stopped being useful.

The same observability discipline that makes any data pipeline trustworthy applies directly here. Once you treat embedding pipelines as production systems, you stop thinking in isolated steps and start thinking in signals. For example, chunk counts per document become a simple but powerful health check, a sudden drop is usually not a model issue, but a sign of broken ingestion or upstream parsing failures.

You also need a “golden set” of queries with known-good outputs. This runs after every pipeline change, much like data quality checks after a transformation. This is how you catch regressions that don’t show up as explicit failures.

On top of that, you can track lineage: Which embedding model version produced which chunks, and when each document was last ingested. That makes it possible to trace retrieval issues back to specific changes instead of guessing.

And finally, freshness becomes a first-class signal. If documents start going stale beyond an acceptable threshold, that should surface in monitoring long before users experience degraded results.

The metric that ties it all together is retrieval quality over time. Treat it like any other pipeline SLA, measured, tracked and owned.

Summary

Embedding pipelines definitely come with a lot of new language, new tools and a genuinely different capability in the semantic layer. But the funny thing is, the principles that actually make them reliable in production are not new at all.

We have versioning, freshness, quality checks and monitoring. These are problems data engineering has already spent years solving.

The real work is taking that same discipline and applying it to a pipeline that just happens to output vectors instead of rows in a table. Once you start seeing it that way, a lot of the chaos around AI systems becomes much easier to reason about.

That’s the difference between building a cool AI demo and building something people can actually depend on. One is a prototype, whereas the other is infrastructure.

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Microsoft has announced Coreutils, a new Windows 11 feature that allows developers to run many popular Linux command line utilities natively on Windows from a single binary.

Revealed at this week’s Build 2026 developer conference in Seattle, Coreutils is about reducing what Microsoft terms the “cognitive load” faced by developers when moving between Windows and other platforms.

Currently, accessing the Linux command line utilities that are considered essential in many CI/CD development environments on Windows requires a kludge that involves either opening an emulation such as Git Bash, or a virtualized Windows Linux Subsystem (WSL) terminal.

Both are time-consuming and inefficient. As Microsoft’s announcement puts it: “Developers constantly move between platforms, but familiar commands don’t work consistently, forcing workarounds, lost speed and context switching.”

Coreutils removes the need for this back and forth, allowing developers to run most Linux commands straight from the Windows CMD command prompt, PowerShell, or Windows Terminal.

“Whether you’re moving between Linux, macOS, WSL, containers or cloud environments, the commands and workflows you’ve built over years just work in your Windows environment,” Microsoft said.

Most utilities, but not all

Installed as a single executable (via WinGet: install Microsoft.Coreutils), Coreutils for Windows itself is a Rust rewrite of the GNU uutils/coreutils project that provides commands that are universal across Linux distros.

Fundamental to making Coreutils efficient to manage is the fact that individual Linux commands run from a multi-call executable which maps via NTFS hardlinks pointing to each command. The advantage of this approach is that there’s only one binary to install, one binary to sign, and one binary to patch or update.

Microsoft lists 75 Linux utilities supported by Coreutils, including commonly-used commands such as ls, cp, find, grep, find, rm, du, hostname, and uptime.

However, some Coreutils commands clash with existing CMD or Powershell commands, or are otherwise not possible to execute; Microsoft provides a compatibility table listing conflicts. This means that some commands are not available, specifically: dir, expand, kill, more, timeout, and whoami.

There are also some commands omitted from Coreutils because a command relies on a POSIX Unix/Linux feature that Windows doesn’t implement in a compatible way; some examples are chmod, chown, id, stty, and chroot.

In other cases, the command will execute in one context, CMD, but not in PowerShell. Microsoft explained the complex order of precedence:  “Whether the Coreutils version runs depends on the shell, the PATH order, and (for PowerShell) the alias table.”

As well as Coreutils, the Build 2026 developer conference also saw Microsoft announce WSL containers CLI and API to deploy Linux containers on Windows, a new framework for autonomous agents with open source governance tools, and Microsoft Scout, an AI agent designed to automate tasks in Microsoft 365.