The Certificate couldn't be validated because SSL negotiation wasn't successful.

Hello All.

I am all of a sudden experiencing an issue with Outlook 2013 being unable to connect to Exchange Server 2013 via IMAP.

The laptop is running Windows 7 Home and as such is not a domain member hence the need for IMAP.

From the Outlook side when setting up the account, it only says "A secure connection to the server cannot be established." on the incoming mail server, but the outgoing checks out OK.

I checked and re-checked all the settings several times on the server. Blogs and forums mostly cover Lync issues with other errors including this one, but nothing with the exact same description.

The setup is "Exchange Server 2013 on a Windows Server 2012 Standard" SSL 993, TLS 587.

OWA and everything else is functioning properly.

Hopes this helps.

Hoping to hear from you soon.

Thank you in advance.

Hentie Loots


September 2nd, 2015 9:09am

The only odd thing I could find on the server is 2 certificates that have no names.

The main "Microsoft Exchange" certificate is the one that has been assigned to all the Services.


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September 2nd, 2015 9:34am

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