I have setup Exchange 2013 and bought an SSL certificate which I installed on the server and is working with my OWA URL.

The issue is with autodiscover which is resolving the incorrect URL meaning I'm getting SSL error. This is my current setup:

Registered working SSL: exchange.domain.com

DNS setup:

email domain: @domain.net

MX: exchange.domain.com

CNAME: autodiscover.domain.net points to exchange.domain.com

When setting up email clients using autodiscover or testing RCA the autodiscover is resolving to  autodiscover.domain.net and not exchange.domain.com resulting in the SSL error. I've setup the external URL in exchange to exchange.domain.com but still getting the error.

Error: host name mismatch - Host: "autodiscover.domain.net" - Certificate: "exchange.domain.com"

Hopefully someone can help out with this.

thanks,

LJ

• Edited by ljac20 14 hours 12 minutes ago

A couple of questions come up in this case:

1. If the email domain is "@domain.net" and you are not using "@domain.com", why do you configure "autodiscover.domain.com"? You need only "autodiscover.domain.net".
2. Is the internal AD domain different from the e-mail domain "@domain.net" (ex. "domain.local")?
3. Are you using a multiple domain certificate or a single domain one?

• Edited by NetoMeter Screencasts 13 hours 41 minutes ago

Thanks for your reply.

1. I will be migrating the domain.com to the same server later on and it will be the primary email. I'm guessing I'll have the same issue there as it will be looking for autodiscover.domain.com and resolving the exchange.domain.com certificate despite the autodiscover CNAME record pointing to exchange.domain.com

2. yes the internal domain is completely different 

3. It's a single domain certificate.

• Edited by ljac20 13 hours 20 minutes ago