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Dear Tim,
Thanks for providing the further information helping us further confirm the scenario in your environment.
May I know whether the users experiencing the issue in both Outlook Web App and the Outlook desktop clients in their environments? If they encounter the issue when using the Outlook desktop clients currently, I suggest you let them try Outlok Web App to do a test and let us know the result.
May I know whether they can go the the SharePoint Online libraries where the attachments are saved and open and edit the attachments normally. If yes, the permission factor can be excluded for this issue. If it is convenient, I suggest you let them use the OneDrive sync clients to sync the attchments and click on Browse this computer>select the local sync folder to attach teh files in an email in the Outlook desktp clients to see and let us know the outcome as well.
Meanhilw, please check whether they are using the same version number of the Outlook desktop clients as the users who aren't experiencing the issue and upload a full screenshot of the Account page in the Outlook desktop clients they are using for our reference.
Note: Remove any private information before uploading the screenshots.
Thanks for your effort and time.
Cliff