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Microsoft has spent the better part of three years trying to make AI a core part of everything it does. Windows 11, Edge, Office, Bing, you name it, Copilot is there. And on paper, I guess that makes sense. Microsoft has invested more than $13 billion in OpenAI, plus it has the infrastructure, user base, and platform to reach numbers of users that very few companies can match. If anyone should be winning in AI right now, it’s Microsoft.
But here’s the thing: almost none of it has landed well. The company’s latest announcement, Copilot Cowork, is probably the clearest example yet of what’s going wrong. It’s an enterprise AI agent that can do things like create presentations, pull data into Excel, and coordinate meetings in Microsoft 365. It runs in the cloud within a customer’s Microsoft 365 tenant, has all the enterprise compliance boxes checked, and works with Microsoft’s Work IQ. It sounds impressive and probably is technically competent. The problem is that the entire concept was invented by someone else, and Microsoft’s version is literally built on that other person’s technology.
Copilot Cowork is powered by Claude from Anthropic. From the outside, it looks fundamentally like the same agent harness as Anthropic itself. Claude Coworka product that launched in January 2026. Microsoft’s response was apparently to take the name, license the technology, and slap a Copilot label on it. If that doesn’t sum up Microsoft’s AI strategy in 2026, I don’t know what else does.
Microsoft keeps building things that already exist
And the originals are usually better.
This isn’t a new pattern for Microsoft, and Copilot Cowork is just the most blatant example yet. Microsoft has been doing this across its ecosystem for years, bringing AI into products where no one asked for it or where better alternatives already exist.
For example, take a look at Copilot in Windows 11. When it was first released, it was a sidebar that could answer questions and adjust some system settings. Users quickly realized that it was, for the most part, a Bing Chat wrapper with some system hooks. Satya Nadella himself reportedly told company engineers that Copilot’s integrations with Outlook and Gmail “don’t really work” and “aren’t smart,” which is pretty remarkable for a CEO to say about his company’s flagship AI product.
According The information In a separate report, Microsoft cut sales targets for Copilot by up to 50%, citing weak demand and the fact that, well, it just wasn’t very good. Microsoft has denied the report, but Dell admitted in a Q&A session that consumers “don’t buy based on AI.”
Then there’s Edge. At this point, Microsoft’s browser has apparently become more of a Copilot billboard than a web browser. The sidebar is there whether you want it or not, the address bar sometimes directs you to Copilot instead of the website you’re trying to visit, and on Windows Insider buildsIf you search for ChatGPT or Gemini on Bing, you’ll get an interactive Copilot widget about five times larger than the actual search result.
Imagine walking into a store, asking about a competitor’s product, and having an employee physically block the exit until you try theirs. This is what it feels like to use Bing now. Users have been vocal about it, and the growing consumer consensus seems to be that literally no one asked for all this AI.
Nobody asked for AI in built-in Windows apps
And yet here we are
Microsoft has also been busy integrating AI into built-in Windows apps, and the results have been as useful as you’d expect. Notepad, one of the most beloved tools in Windows precisely because Thanks to its simplicity, it now has built-in write, rewrite and summary functions. You can even choose a tone, from formal to humorous. I’m sure someone is using Notepad to compose formal correspondence with the help of AI, but I can’t really imagine who that person is.
Paint got a similar treatment with AI-powered image generation, generative editing, and even a coloring book feature. Photos have background removal, AI enhancement and generative deletion. These aren’t bad features in isolation, but they already exist in better, more dedicated tools. If I want to edit images with AI, I’ll use something designed specifically for that. If I want generative text, I’ll go to the model directly instead of going through Notepad. The fact that free Microsoft accounts only get a small amount of credits per month for these features makes the whole thing feel less like a value-add and more like an upsell.
In both writing and image editing, Microsoft fell far behind the rest of the industry. And all that without getting into Windows Recall, one of Copilot’s few unique offerings. Announced in May 2024, Recall takes a screenshot of your desktop every few seconds and uses on-device AI to make everything searchable. Never lose track of anything you’ve seen on your computer, that was the pitch.
The reality was a privacy disaster. Security researchers caught it almost immediately. The initial version saved all data in a plain text database, making it trivially easy for anyone with access to your machine to see everything you had done on it. Microsoft delayed the release, accepted it, added encryption, and required Windows Hello authentication. It was finally released in April 2025, and even then, PCWorld’s review basically said, “I like the AI, but I can’t trust it.” Remembering solves a problem that most people didn’t have, in a way that creates problems for most people. definitely I don’t want to.
To its credit, Microsoft seems to be listening at least some of the feedback. Reports from early 2026 suggest that the company is rolling back some of these integrationsremoving Copilot features from built-in apps and focusing on fixing long-standing performance issues in the Start menu, taskbar, and File Explorer. That’s good, but it also begs the question: why did it take so long to realize that people wanted a faster Start menu and a system that actually worked more than they wanted the AI in Notepad?
Copilot Cowork says it all
When your greatest flexibility is someone else’s technology
What makes Copilot Cowork so telling is how loudly it announces that Microsoft can’t solve this alone. The company has invested billions in OpenAI, and yet when it came time to create its most ambitious AI agent product, it turned to Anthropic. Not because of some grand multi-model strategy, but because Anthropic had already built what Microsoft wanted to build, and it clearly worked better than Microsoft could do with OpenAI models alone.
Anthropic’s Claude Cowork launched in January, is available to regular consumers and integrates with tools like Google Drive and Gmail. Microsoft’s Copilot Cowork does pretty much the same thing, but locks it into the Microsoft 365 ecosystem and, for regular use, requires an E7 license level that most organizations don’t have. Microsoft 365 business users will get “some use” at the company’s $30 a month tier, according to Reuters. This is all the same concept as Anthropic’s product but with a different, less accessible and more expensive label. To be clear, that’s not innovation, it’s a licensing agreement with additional steps.
It’s the same playbook every time it comes to Microsoft’s AI strategy. Microsoft sees what works elsewhere, builds its own version within the Microsoft ecosystem, and pushes it aggressively across the platforms it controls. When users resist, the company quietly scales things back and moves on to the next AI integration. Bing Chat became co-pilot. Copilot became Copilot+. Copilot+ became Copilot Cowork. The brand changes, the underlying approach remains the same.
I get it, Microsoft is a platform company. It makes sense that you want AI to be integrated into everything. But there’s a difference between putting AI where it really adds value and bombarding every product with features that exist primarily so Microsoft can say it has them. Right now, the tools that people can use outside of the Microsoft ecosystem are simply better. Microsoft doesn’t need more AI capabilities; It needs fewer and better ones that really solve the problems people have.
