Using Classic Outlook on Windows for personal email, calendar, and contact management
I have been back-and-forth with Microsoft Support with this same issue for the past month.
I have tried many different fixes, some recommended by Microsoft and some from my own online research, but none have worked.
It only seems to happen when sending from the Outlook application in Windows 11, but not Outlook Live in Chrome, or the Outlook App on the iPhone.
It also only seems to happen when sending from my ...hotmail.com account, and not from my ...outlook.com account.
It also does not happen every time. Sometimes the From entry resolves to my name (as detailed in my Contacts), sometimes it remains as the full email address, and sometimes is jus remains as the ORGANIZATION/OU=... text.
Possibly unrelated, but it has been happening around the same time, is that Outlook requests that I re-enter my password several times per day (I have created a new Profile several times, but to no avail).