Using Classic Outlook on Windows for personal email, calendar, and contact management
I just got Microsoft on the phone (I called into 800-865-9408, waited about 30 minutes for someone) and this is what they had me do to fix this issue:
Login to https://admin.microsoft.com
On the left pane, click Show All > Settings > Domains
My main domain had an issue under the Status column to show that we were having a problem
Click the 3 dots and choose Manage DNS
Click Continue twice and it will take you to your domain setup. I had a handful of SPF records listed and it says that you can only have one. This was my problem.
I logged into my DNS Server (my host uses cPanel) and went into the section where the TXT and CNAME entries are (I think it's called Zones in cPanel)
I looked through and found all of the SPF entries (literally just ctrl+F SPF to find them) for the main domain - sub-domains didn't matter for me.
I went to Chat GPT and asked it to help me combine the SPF records and copy/pasted all of the ones I had in there (YMMV with Chat GPT). I used the output and pasted it into a TXT entry and deleted the others.
I went back to Microsoft and it recognized that I only had the one SPF record and it looks fixed now.
Hope this helps someone!