Email stopped working months ago for just 1 queue
The queue that is sending emails uses smtp.office365.com and port 587. I used the exact same settings for the new queue and it worked at first but back in February it just stopped sending emails. I've verified the password is correct and was able to log into the email.
The Exim Main Log is as follows:
2019-09-24 14:13:29 1iCqFd-000DOT-Ps <= Email@Domain.com U=www P=local S=923
2019-09-24 14:13:29 1iCqFd-000DNt-1s => Email <Email@Domain.com> R=helpdesk T=helpdesk_pipe
2019-09-24 14:13:29 1iCqFd-000DNt-1s Completed
2019-09-24 14:13:30 1iCqFd-000DOI-MO [18.104.22.168] SSL verify error: certificate name mismatch: DN="/C=US/ST=Washington/L=Redmond/O=Microsoft Corporation/CN=outlook.com" H="lyh-efz.ms-acdc.office.com"
2019-09-24 14:13:36 1iCqFd-000DOI-MO auth_login authenticator failed H=lyh-efz.ms-acdc.office.com [22.214.171.124] 535 5.7.3 Authentication unsuccessful [BN6PR2001CA0018.namprd20.prod.outlook.com]
2019-09-24 14:13:44 1iCqFd-000DOI-MO == myEmail@Domain.com R=smart_route T=transport_587 defer (-42): authentication required but authentication attempt(s) failed
2019-09-24 14:22:06 Warning: purging the environment.
it does not like microsofts cert any longer
see this article "Microsoft to Bid Farewell to SHA-1 in February"
In case I stumble on this question again in the future, this issue happened again. I tried resetting the password and used a random generator come up with one. I could authenticate and login to the outlook app manually but emails were not sending. I manually created a less complex password and suddenly the emails were sending again. So perhaps there is a password limitation somewhere on the pipeline that limits characters.