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?

• Edited by BomBomBomBom 19 hours 39 minutes ago

Would you tell us more about certificate that appears during Certificate error? It's CN/SAN?

Have you tried to run remote connectivity analyzer?

Hello,

1. Check, if there are other certificates also presented. If so, you can remove those safely.

2. Do you have any reverse proxy mechanism like ISA etc? if so make sure that the certificate is imported there too

3. Go to www.testconnectivity.microsoft.com and do an outlook auto config test and see if there are some certificate issues

4. Check the event log of the server and see if there are some errors/warnings etc.