Using Classic Outlook on Windows for personal email, calendar, and contact management
Hello, I am having the same issue with a client of mine.
The error message stating the message has expired means 365 has been trying to deliver it. Socket error is probably the destination server dropping the connection. Most likely incorrectly set spam filter. We are getting nowhere with Yahoo. I would try getting a free email account like gmail and set it up in Outlook. Then send the email under the gmail account rather than your domain. That will tell you if it is a spam problem. If it goes through, your domain is blacklisted at Yahoo.
Here is the catches... *You mail sent under gmail will show up as sent by gmail, not your domain.
* Yahoo users Spamhaus. You can go there and look at the blacklist. I did that and domains in question are not there. So, they had to add a new spam filter and it is messing things up. Can't find any information on Yahoo with new spam filtering.
The bounce back does say, SFP and DKIM pass. Those are not the problem.
Still working on the problem, will update if solution is found.
Joel