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 [] 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 [] 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.

2 Comments   [ + ] Show comments
  • The first thing I am noticing is the SSL verify error. Does the working queue get that error as well? - jonniipalos 2 years ago
    • Yes it does. I almost wanted to take that out because I'm not sure if it has anything to do with the email not working. - caitlynmcorey 2 years ago
  • I fixed the issue. It was the password. I can't explain it. I used the same password to log into outlook and it worked. Reset the password and now it's firing off emails again. Go figure. - caitlynmcorey 2 years ago

Answers (3)

Answer Summary:
Posted by: SMal.tmcc 2 years ago
Red Belt

it does not like microsofts cert any longer

see this article "Microsoft to Bid Farewell to SHA-1 in February"


  • Good to know for the future since we'll be implementing Service Desk pretty soon. - jonniipalos 2 years ago
  • This appears to be old. I got excited when I saw February because Feb 2019 is when it stopped working but I'm not sure this issue has anything to do with the email not working. - caitlynmcorey 2 years ago
    • have you tried to restart the kbox to see if it helps
      also what version of kbox? - SMal.tmcc 2 years ago
      • I believe we have. Last week we upgraded so I assume it would have been restarted then. The problem occurred long before the upgrade and is still a problem after the upgrade. - caitlynmcorey 2 years ago
      • have you tried to run a connection test on the Service Desk › Configuration › Service Desk Queue Email Settings page to see what results you get? - SMal.tmcc 2 years ago
      • Weird it won't let me reply to your other comment. Yes I did try the connection test.

        Connection Test SMTP
        [Wed Sep 25 11:15:54 CDT 2019] Starting SMTP connection test to smtp.office365.com:587.
        [Wed Sep 25 11:15:54 CDT 2019] Sending SMTP test email to myEmail.
        [Wed Sep 25 11:15:56 CDT 2019] Test email was successfully sent.
        [Wed Sep 25 11:15:56 CDT 2019] SMTP Connection test is successful. - caitlynmcorey 2 years ago
Posted by: caitlynmcorey 2 years ago
White Belt

Top Answer

I fixed the issue. It was the password. I can't explain it. I used the same password to log into outlook and it worked. Reset the password and now it's firing off emails again. Go figure.

  • FM
    at least you got it going again. Does someone else have access to this area? Something like unchecking and rechecking the smtp setting box could reset that. I have seen little things like that change stuff it should not. If you do not have history tracking enabled I would turn it on, that helps to track "unknowns" you can track settings changes that way - SMal.tmcc 2 years ago
    • Where is the history tracking setting? - caitlynmcorey 2 years ago
      • I have multi orgs so it is in system and each org separately. In the left column click on settings and you will see history under that. Subscriptions settings configures what setting changes to track and reporting lets you see the history You can also track asset and object changes under the other buttons - SMal.tmcc 2 years ago
    • Looks like we have history enabled forever. But I'm not sure when it was enabled. Everything looks new like it was just enabled when we upgraded. - caitlynmcorey 2 years ago
      • I only keep a month so I don't know if the 10 upgrade clears that as part of its house keeping or not, been on 10 since June (beta) - SMal.tmcc 2 years ago
Posted by: caitlynmcorey 1 year ago
White Belt

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. 

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