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mmj1Flag for United States of America

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Outlook 2016 - security certificate issue when opening outlook

I have Office365 locally installed on a PC with the email account setup as IMAP.  All was working ok but now have a few issues:
1) When opening Outlook frequently (not always) getting a send/receive error - usually a reboot will correct
2) Yesterday - started getting the following message:  "Internet Security Warning" - The server you are connected to is using a security certificate that cannot be verified..... do you want to continue using this server.

I have two different email accounts setup in Outlook (one goes through Yahoo servers and the other through Total Server Solutions (previously Hands On Webhosting) - both accounts are setup as IMAP.

Any help is appreciated!  Thank you.
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Scott Kunau
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Avatar of David Favor
My guess is this relates to a broken load balancer or proxy.

Better to test + know, than guess.

Provide the hostname of the IMAP server you're connecting to for testing.

If you must do this yourself, what you're looking for is if the IMAP instance has a fixed IP or an IP pool.

What you describe sounds like an IP pool, where one or more IPs have some config which is incorrectly serving your cert.
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ASKER

Thank you both for your input.  After further review, we think this issue with the "Internet Security Warning" is due to a site we are navigating to that needs to renew the SSL certificate - that is being worked on so I'll know once they renew it if that was the problem.   I am going to close this question and award you both points for your assistance.  If the cert issue is not resolved by the renewing of the cert I may need to log another question.  Thanks again.