Hi @bimmerdriver ,
Welcome to Microsoft Q&A forum.
Before going further, the AutoComplete list for Outlook is specific to Outlook and is not shared by Outlook Web App (OWA). OWA maintains its own AutoComplete list. So, the AutoComplete feature in OWA might not be useful for us to troubleshoot our client issue.
As you have mentioned, the "empty the auto-complete list" method and the "delete the Outlook Roam Cache" are both common method for AutoComplete issues in Outlook client. Since it could indeed work for a while, so we might be able to refer that the issue should be related to the AutoComplete cache in your computer.
It’s possible to create an email or meeting invitation for “both” of these users, but Outlook will automatically remove whichever one I entered second after a few minutes.
Are both the "normal" and "abnormal" AutoComplete entries all real-existed user's email address? Or the "abnormal" one is an empty email address?
According to my tests in my Outlook 365, when sending emails to both valid email address and invalid email address, Outlook will not automatically remove any entries in the "To" list, we will just receive a NDR messages about the invalid email address but all the addresses are still remained in the "To" list. As I know, there could be some add-ins in your Outlook client that influence your AutoComplete cache and cause issues like this, so it is suggested to empty your AutoComplete list and start your Outlook in safe mode (Press Win + R, type “outlook /safe”, press Enter.) and see if the issue continues.
By the way, are you using Outlook desktop client along with other third-party programs? Antivirus software and other third-party programs might also cause issues like that. So, if possible, please try to empty your AutoComplete list and exit your Antivirus software to see if this issue could still be reproduced.
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