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Random Certificate Popup (Outlook 2013 / Exchange 2013)

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Hi everyone,

Any help would be gratefully received!!

Quick summary

Exchange Server Name: SERVER.DOMAIN.NET

External Host Name: MAIL.DOMAIN.COM

SSL Certificate: MAIL.SERVER.COM / AUTODISCOVER.DOMAIN.COM / OWA.DOMAIN.COM.

All Virtual Directories have both internal and external URLs set to MAIL.DOMAIN.COM

During the AutoDiscover process there is no certificate prompt, however after a short while it does appear with name mismatch. Clicking do not accept doesn't take Outlook Office and performing a Test Email Configuration (which would normally bring it up if it was an autodiscover problem) doesn't make it appear.

It just simply appears after a couple of minutes saying the internal name doesn't match the certificate.

I've configured the SVR Record internally for Autdiscover which by all accounts should resolve it (if that was indeed the issue) but it hasn't.

I can't for the life of me find what Outlook 2013 is actually doing to see this internal hostname over SSL to receive this prompt. Has anyone got any suggestions or come across anything similar?




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