A much-requested feature has arrived in Microsoft Copilot. The AI chatbot can now handle multiple file uploads (including images) at once. This update is already live for all users on the app or in-browser if you want to play around with it right now. Plus, Microsoft is already asking users to share their results over on its Copilot Discord server.

Copilot has had some pretty interesting updates lately, notably adding an expressive mascot with a friendly face as an introduction to its Copilot Appearances feature that was originally shown off earlier this year.

Multi-file upload in Copilot is now available

It feels like AI chatbots are always playing catch-up with OpenAI’s leading ChatGPT feature set, and now Copilot is one step closer to it. There’s even support for the latest GPT-5 model within Copilot. In any case, multi-file upload is a welcome addition – and something that users have been asking for. Microsoft even opens its announcement post with “You asked, we shipped!”.

Copilot now supports multi-file upload This one’s been a popular ask across the community, and it’s now here. You can upload up to 3 files or images at once – Copilot will read across them to give you a more complete answer. Copilot doesn’t just look at them one by one, it can actually connect the dots between them.

Copilot can reason across multiple uploads at once Instead of treating each file like a separate task, Copilot now reads across all three – so it can spot patterns, compare details, and give you a fuller picture in one go.

Quick rundown:

• Upload up to 3 files/images
• Copilot can reason across them, not just separately
• Better image understanding too

Source: Microsoft Copilot Discord

We tasked it with spotting the odd one out from a selection of graphics cards we’ve reviewed, and while it correctly identified that we were looking for the Founders Edition as the odd one out, that’s the RTX 5080 FE pictured – not the 3090. Likewise, it’s an ROG Astral card, not a ROG Strix. Both Copilot’s ‘Quick Response’ and ‘Smart (GPT-5)’ options gave us a similarly inaccurate response. But at least it can separate an FE card from a partner one.

The process is simple. Within Copilot, click the plus icon, click upload, and choose multiple files. You can then accompany this with a message or a question to ask Copilot to do something using the images as a reference. The feature allows the AI to reason across them and compare, rather than separately. A few of Microsoft’s suggestions include using multi-upload to compare job offers, building a moodboard from a few screenshots, or helping you study for a test by uploading notes or textbook excerpts.

About the Author

Jack Goodall

At PC Guide, Jack is mostly responsible for reporting on hardware deals. He also specializes in monitors, TVs, and headsets and can be found putting his findings together in a review or best-of guide.