Microsoft has quietly introduced ChatGPT’s advanced multi-file analysis support to the web and Windows 11 versions of its Copilot app. This feature is available without a paid subscription. Copilot previously supported uploading up to 20 files in a single message, but it processed each file individually and was unable to correlate the files. With GPT's multi-file support, Copilot can finally read multiple files simultaneously.
Microsoft confirmed that Copilot can now read up to three files simultaneously. For example, if you're changing jobs and have up to two job postings and a resume, you might want Copilot to be able to read all three files simultaneously and concatenate the information.
Copilot knows how files are related. Microsoft says this is one of the most requested features in the community.
Copilot has most of the free features of ChatGPT, including GPT-5 with Thinking. Oddly, Copilot is unable to process and read files at the same time, something ChatGPT has always had.
Since Copilot offers limited-message GPT-5 thinking to free users, it can now also perform inference on up to three files simultaneously.
For example, you can use Copilot's powerful multi-file system to analyze travel plans, uploading budgets, travel itineraries and baggage details to identify deficiencies or improve routes/strategies to reduce costs.
Copilot now has a "Learning" mode. It gets even better when combined with the new multi-file support feature. To try "Learn" mode, just select the "+" menu and select the appropriate option.
Once you enable Copilot's "Learn and Learn" mode (which is exactly the same as ChatGPT's learning model) and upload three learning documents, Copilot can combine all of them to create a practice quiz. I asked Copilot to create a flashcard-based quiz using three documents I uploaded.
As you can see in the screenshot above, Copilot combined the three files and created a quiz. I can select options in the Copilot interface and the AI will give me a score. Additionally, it provides explanations.
Another potential use is in book reading order. For example, if you take a photo of a friend's bookshelf, or screenshot a few book covers, Copilot can help you get the title/information for each book, organize them by topic, suggest a reading order, and even generate summaries and discussion prompts for book clubs.
Advanced file analysis capabilities aren't the only new addition to Copilot this week. The latest version of Windows recently discovered a new audio expression feature on Copilot. Unlike ChatGPT, it uses an internal Microsoft model that sounds more natural and personal.