Hands-on With New "Ask M365 Copilot" Feature in Windows 11 File Explorer

Microsoft has found itself in the midst of growing scrutiny by Windows users for adding AI in all parts of the operating system. Thousands of users recently blasted Windows chief for his post on X, where he mentioned “Windows is evolving into an agentic OS.” Despite all the backlash from Windows community, Microsoft isn’t stopping.

At Ignite 2025, Microsoft announced that File Explorer would eventually get the new “Ask M365 Copilot” feature on hover that can help you ask Copilot more about files. Speaking about it, Microsoft mentions that “you can enjoy streamlined file productivity without leaving their current context.” Think of it asking AI what’s in there without having to open long PDFs, images, and more.

Although the company noted that the feature would roll out before the end of 2025, I can confirm it’s out for Windows Insiders. So, how does the feature work, right? Well it’s quite easy. You can simply open the File Explorer and hover on a file, and you’ll see a grayed-out Copilot icon. When you hover on the icon, you see a message, “Ask Copilot about this file.”

Once you click on it, Copilot app opens in the background and as you can see below, you can ask whatever you can. For example, I chose an Xbox’s banner image from yesterday with multiple titles featured on it. Without opening the file, there was no chance I could name all them, but as you can see below, Copilot pulled all the names with utmose ease, and that too without fumbling.

If you are someone who works around bunch of documents on a daily basis, the new “Ask M365 Copilot” feature is definitely handy.

All that said, I am still scratching my head that the “Ask Copilot” option is already there in the context menu, so why this? If this then why not remove that? Well, I guess Microsoft’s obsession of flaunting Copilot everywhere across OS won’t stop soon, thanks to Mustafa Suleyman, who recently took a jab at critics saying “It cracks me up when I hear people call AI underwhelming…. The fact that people are unimpressed….is mindblowing to me.”

Article feature image source: Microsoft