Microsoft has quietly rolled out ChatGPT’s advanced multi-file analysis support to Copilot on the web and Windows 11. It works without a paid subscription. Copilot already supports up to 20 files uploaded in a single message, but it processes every file individually, and it cannot connect the dots. With GPT’s multi-file support, Copilot finally reads files together.
I asked Microsoft for more details, and it told me that Copilot can now read up to three files together. For example, if you’re planning to switch day jobs and have up to two job listings and a resume, you might want Copilot to go through all three files and connect the dots.
Copilot knows how the files are related to one another. Microsoft says it’s one of the most requested features in the community.
Copilot has most of the features available in ChatGPT for free, including GPT-5 with Thinking. It was quite odd that Copilot did not have the ability to process and read files together while ChatGPT always did.
Since Copilot has GPT‑5 Thinking with limited messages for free users, it can now also reason across up to three files at once.
Similar to the example I shared above, you can use Copilot’s powerful multi-file system to analyze a travel plan. You could upload your budget, travel route, and luggage details to spot gaps or improve the route/strategy to reduce costs.
I tested Copilot’s multi-file system with Study and Learn, and it’s phenomenal
Copilot now has Study and Learn mode. And if you combine it with the new multi-file support, results are even better. To try Study and Learn mode, just select the “+” menu and choose the option.
Once Copilot’s Study and Learn mode, which is an exact replica of ChatGPT’s Study model, is turned on, and you upload three study documents, Copilot can process all these files together to create a practice quiz. I asked Copilot to create flashcards-based quiz using the three documents I uploaded.
As you can see in the above screenshot, Copilot processed the three files together and created a quiz. I can select options within the Copilot interface, and the AI then follows up with a score. In addition, it offers explanations.
Another potential use could be a books read order. For example, if you capture a photo of your friend’s bookshelf or a few book covers you’ve screenshotted, Copilot can help you get the titles/info for each, organize them into themes, suggest a reading order, or even generate summaries and discussion prompts for a book club.
Advanced file analysis feature isn’t the only new addition for Copilot this week. Windows Latest recently spotted a new audio expression feature on Copilot. Unlike ChatGPT, it uses Microsoft’s in-house model and sounds more natural plus personal. In fact, it stands out in our “story telling” tetss and I recommend giving it a try because it’s free.
