troubleshooting Question

Exchange 2019. Outlook clients get warning about certificate

Avatar of Martin_Radbo
Martin_RadboFlag for Sweden asked on
ExchangeOutlookWindows OS
16 Comments2 Solutions179 ViewsLast Modified:
Complete new installation of servers and clients.

One single server with Windows Server 2019, containg AD and Exchange server 2019.
Clients are WIn 10 Pro, joined to domain, with Outlook 2019.

Internal domain name is stsgroup.local, to late we realized that a public domain name is best practice theese days. But now we have an internal one...

When Outlook clients are setup for the first time, the following message are shown:

error.png
As you can see, they try to use the internal domain name and therefor the warning is issued.

The certificate is a SAN, with autodiscover.domain.com,  webmail.domain.com and mail.domain.com. It is installed on the server.

I have changed all of the URL:s for the virtual dir. to https://webmail.domain.com/...  

Split DNS are configured, so in the internal dns autodiscover.domain.com and webmail.domain.com are pointing to the internal ip of the Exchange server, i.e. 192.168.140.40

The external DNS are pointing to the public IP of the Exchange server.

I have read several posts about this, but it still fails.

Please help.
ASKER CERTIFIED SOLUTION
Join our community to see this answer!
Unlock 2 Answers and 16 Comments.
Start Free Trial
Learn from the best

Network and collaborate with thousands of CTOs, CISOs, and IT Pros rooting for you and your success.

Andrew Hancock - VMware vExpert
See if this solution works for you by signing up for a 7 day free trial.
Unlock 2 Answers and 16 Comments.
Try for 7 days

”The time we save is the biggest benefit of E-E to our team. What could take multiple guys 2 hours or more each to find is accessed in around 15 minutes on Experts Exchange.

-Mike Kapnisakis, Warner Bros