We have Similar situation to this. I have EX2013 configured initially with server FQDN in Outlook Anywhere URL (server.domain.internal) and other services as well (Autodiscover, OWA,EWS) with self signed certificate.

Now we have deployed a new certificate to reflect mail.domain.com (Along with Autodiscover.domain.com) as SAN name in it.

After deploying the certificate (Still the URL’s pointing to server FQDN), outlook clients started displaying certificate error.

We have changed the URL’s to match the SAN name in certificate (mail.domain.com)

Do we need to reconfigure the outlook clients again?

We see still clients connects to old URL and showing certificate error, however Auto discover test connects to new URL.

Note: Creating New profile works fine. However old profiles still displays certificate error.

Hi Paul,

We have Similar situation to this. I have EX2013 configured initially with server FQDN in Outlook Anywhere URL (server.domain.internal) and other services as well (Autodiscover, OWA,EWS) with self signed certificate.

Now we have deployed a new certificate to reflect mail.domain.com (Along with Autodiscover.domain.com) as SAN name in it.

After deploying the certificate (Still the URL’s pointing to server FQDN), outlook clients started displaying certificate error.

We have changed the URL’s to match the SAN name in certificate (mail.domain.com)

Do we need to reconfigure the outlook clients again?

We see still clients connects to old URL and showing certificate error, however Auto discover test connects to new URL.

Note: Creating New profile works fine. However old profiles still displays certificate error.

You should probably try a network trace with Fiddler or a similar tool so you can see where the client is connecting. Or open a support case with Microsoft.

It means that machines that don’t have the latest root certificates might not trust your certificate. It’s just a warning that mostly impacts older machines or those that don’t allow root certificate updates.

While running test connectivity i get
The Microsoft Connectivity Analyzer can only validate the certificate chain using the Root Certificate Update functionality from Windows Update. Your certificate may not be trusted on Windows if the “Update Root Certificates” feature isn’t enabled.
Elapsed Time: 2 ms.

Outlook clients will receive the new URL via Autodiscover. It will only impact Outlook Anywhere connections. On the LAN, Outlook uses RPC/MAPI to connect, not Outlook Anywhere, so they won’t be impacted unless you’ve got the config in place that forces them to use Outlook Anywhere all the time.

may be its quite simple question but still want to double confirm, lets say if i change OA url, will outlook clinet affects?
there will be two scenerio as per my understanding,
1. what will happen with outlook clinet which is configured using autodiscover?
2. what will happen where profile is been configured manually?

Thanks in advance!