How to enable upload files to Copilot word

Erwin Stedronsky 0 Reputation points
2026-09-09T22:21:01.93+00:00

Microsoft 365 Personal subscriber on Mac. Word version 16.95.4 (25040241). Copilot is available and Connected Experiences are enabled. In Copilot, "Upload file" is visible but always grayed out, even in a new blank document. I am signed in as the subscription owner.

Microsoft 365 and Office | Word | For home | MacOS

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  1. Xavier-D 12,515 Reputation points Microsoft External Staff Moderator
    2026-09-10T03:18:56.82+00:00

    Hello Erwin Stedronsky

    I can see that you are having issue with Copilot in Word

    You listed the version, the license, and the settings, which saves a lot of back and forth, and it is understandable to be puzzled when a button is visible but permanently disabled.

    For a home Copilot account, referencing a file is only available when using Word for the web. If that applies to your Personal subscription, no amount of resetting the Mac desktop app will enable the button, because the capability is not offered there.

    Two things worth trying next:

    • Open the same document at office.com in Word for the web, signed in with the same account, and check whether the file option becomes selectable there. If it works on the web but not on the desktop, then the web version is the workaround for now.
    • In the Copilot chat pane, type / and begin typing a document name instead of using the upload button. This is a way to point Copilot at a file, and it sometimes works when the upload control does not.

    One more thing to rule out: Copilot in the Microsoft 365 apps on a Personal plan uses monthly AI credits and feature limits. Sign in to your Microsoft account and open Services and subscriptions to see whether your allotment has been used up for this cycle, since exhausted credits can leave Copilot controls unusable.

    Please let me know what happens in Word for the web, since that result tells us whether this is a plan limitation or something specific to your Mac install.

    Feel free reply back to this post and update me on this issue, I'll be happy to help.

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