Outlook finally fixes the Mac file attachment bug in latest update

After months of frustration, it’s finally here: Microsoft has rolled out a much-needed fix for Outlook on Mac that tackles the long-standing issue with file attachments. For many, attaching files to emails had become a guessing game of “Will it work today?” or “Do I need to restart my Mac again?” But now, version 16.90.3 of Outlook brings relief to users who’ve struggled with this glitch since it first popped up.

For those blissfully unaware, Outlook on Mac had developed a nasty habit of graying out attachment options, making it impossible to attach files or preview them. Users were forced to restart their Macs just to send a simple email with attachments. Some even resorted to using the Outlook web version as a workaround while switching to Legacy Outlook became a popular quick fix for those who just couldn’t deal with the constant interruptions anymore.

The issue was widespread across various versions of macOS, from Sonoma to Sequoia, and wasn’t limited to specific Mac models. Users across the board, from MacBook Pro owners to iMac aficionados, found themselves unable to perform a basic email function — one that’s critical for anyone who relies on Outlook for work.

With the latest version 16.90.3 of Outlook on Mac, Microsoft has finally addressed the attachment glitch that has been driving users up the wall. The update, now available through the Apple App Store, promises to restore full functionality to the attachment context menu. That means no more grayed-out options, no more restarts, and, yes, it’s safe to say goodbye to Legacy mode (unless you’re one of those who just prefers the classic feel).

The changelog lists this update as a fix for the attachment options being disabled in Legacy Outlook — though the impact goes beyond just the Legacy users. Now, all users, whether they’re on the latest Outlook or had rolled back to avoid the glitch, can enjoy a seamless experience again. Here’s the full changelog:

• Mail: Fixed an issue that may cause users to lose access to Copilot features.
• Mail: Fixed an issue where options in the attachment context menu are incorrectly disabled in legacy Outlook.

For those using Copilot features within Outlook, the update resolves a separate bug that had been causing users to lose access to some AI-powered tools, giving yet another reason to update. Interestingly, there are several other users who simply dislike the idea of Copilot within their Microsoft 365 Apps such as Word and are even exploring ways to disable or completely remove it from their environment.

If you’re ready to say goodbye to file attachment headaches on Mac, updating to Outlook version 16.90.3 is simple. Just open the app, go to “Help” in the menu bar, and select “Check for updates.” Or, for the easiest route, visit the Apple App Store to snag the latest version directly.