Hi @Echua ,
My boss has been receiving attachments normally until recently when she got her m365 installed.
Are the boss and you using the same kind of email account(for example, both are Exchange account in the same organization)?
According to your description, the issue only happens after using Outlook 365 desktop client. So, in order to confirm if the issue is related to the Outlook desktop client, it is suggested to check these attachments directly from the web mail and see if the issue has any difference. Or, if possible, you could try to add the problematic email account to those normal Outlook clients and see if this issue could be reproduced.
Any update, please feel free to post back.
If an Answer is helpful, please click "Accept Answer" and upvote it.
Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.