A Microsoft file hosting and synchronization service.
Dear Charlie1008
Good day! Thank you for posting in Microsoft Community. We are happy to help you.
Based on your description, it seems that when the ai file synced to the Mac folder, you can't open the file on Mac, but you can open it OneDrive website on Mac.
Given this situation, to narrow down if the behavior is related to OneDrive app on your Mac, please kindly sync another file from PC to your Mac then check the behavior.
Besides, please try the following steps to check the behavior:
- Unlink OneDrive by click OneDrive icon, choose Preferences, then About, click **Unlink>**sign-in back again ad see the outcome.
- Remove the OneDrive account credentials on your Mac then to sign in again to check the result
- Open Finder> Applications> Utilities> Keychain Access.app
- Search for Microsoft Office> Delete all the items that contain MicrosoftOffice… by right-clicking on it.
- After removing Office credentials, press Command + Shift + G (while Finder is opened)> enter ~/Library, search OneDrive.
- Delete all folders and files which names include com.microsoft.OneDrive.
- After performing each step above, restart your Mac> Launch Word application> Sign-in.
- Reset OneDrive on your Mac then see the outcome, for your reference: Reset OneDrive (microsoft.com)
Besides, to help you better, we would like to collect more detailed information you're experiencing so that we can have a further investigation:
- Does only the specific .ai file have this behavior or all files have this behavior when sync from pc to Mac?
- Can you tell us your OneDrive version? On the menu bar at the top of the screen, select the cloud icon. Help & Settings > Preferences.Select About, and share the screenshot to us.
If there are any misunderstanding or unclear, you can post back in your free time. We’re looking forward to your reply and will continue to help you all the time!
Your understanding and patience will be highly appreciated. I hope that you are keeping safe and well!
Sincerely,
Stacey | Microsoft Community Moderator