Embedded images in Outlook 365, switching to attachments

[SMR1]

Has anyone seen this issue where when a user is sending an email to either a windows device or another Mac using office 365 and it has embedded images, but the when the other user gets it, it switches to an attachment. It's hit and miss and eventually goes away and we think it's only this one user that has issues. Our exec support is still trying to schedule a time to troubleshoot because it got escalated up and this user is a EA. The user sending the emails is on 16.87 and the user getting the email is on 16.88. 

[AJPinto]

This would be a configuration on the Microsoft/Exchange/Outlook side somewhere. Microsoft has scripting going on with Outlook for all kinds of things to ensure compatibility. You could update Outlook on the EA's device to make sure they all have the same version to try to reduce compatibility issues.

For example with random scripting workflows: If you attach and email a .msg to a Mac, Outlook will reformat the attachment to .eml which macOS can natively open. Seems like it would be easier to add support for the .msg file extension to Outlook, but I digress.