Outlook 2016 not sending mail

I have a workstation that has Outlook 2016 loaded, the user has access to two mailboxes, each on a separate domain but running off the same Exchange 2013 server.
Both mailboxes can receive mail just fine, one can send, the other can't. Logging into OWA shows that the problematic mailbox does work as it can send and receive mail without issues. I have recreated the ost file, repaired Office and am still not able to get it to work.

Error attached.
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DJMohrAsked:
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Ashish SinghConnect With a Mentor Data ScientistCommented:
Hi,

There can be many reasons behind this issue. Please check below link to fix your Outlook issue:
https://support.office.com/en-us/article/My-messages-won-t-send-97748418-bbd5-4743-a05b-581f22a466dd

Regards
Ashish
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Jackie ManCommented:
It is very likely to be an SSL cert problem.

Are you using UCC (SAN) cert on the said  Exchange 2013 server?
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DJMohrAuthor Commented:
Recreating all outlook profiles solved the issue.
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