Outlook clients receiving Security Alert with SSL Certificate


I recently re-keyed the SSL certificate for a Exchange 2010 server because the common name in the certificate was not correct. Upon importing the certificate into the certificate store and enabling it for SMTP, POP, IIS and IMAP, all of the Outlook 2007 and Outlook 2010 clients are now receiving a Security Alert "The name on the security certificate is invalid or does not match the name of the site." They were having to click the Yes to proceed button twice until I followed the procedure to change the autodiscover and other components URLs at Microsoft's site:


The server does not use UM, so I did receive an error when attempting to run the related commandlet.

The clients are still receiving the SSL Security warning when opening Outlook, however they only have to acknowledge the error once before Outlook connects to the server.

Any experts know what else I need to do to resolve this issue?
Who is Participating?
I wear a lot of hats...

"The solutions and answers provided on Experts Exchange have been extremely helpful to me over the last few years. I wear a lot of hats - Developer, Database Administrator, Help Desk, etc., so I know a lot of things but not a lot about one thing. Experts Exchange gives me answers from people who do know a lot about one thing, in a easy to use platform." -Todd S.

Can you please run the following commands and share the output as I would like to check the URLs:

get-ClientAccessServer  | fl
get-WebServicesVirtualDirectory | fl
get-OABVirtualDirectory | fl
You need to update the name being used to answer the requests.

Replace "CAS-Server-Name" with the name of your exchange server that holds the Client Access Server Role.
Replace "mail.example.com" with the name of the mail server URL that you put in your certificate.

Modify the following commands:
Set-AutodiscoverVirtualDirectory -Identity 'autodiscover (default Web site)' -ExternalURL 'https://mail.example.com/autodiscover' -InternalURL 'https://mail.example.com/autodiscover' -BasicAuthentication $true
Set-OABVirtualDirectory -Identity "CAS-Server-Name\OAB (Default Web Site)" -ExternalUrl "https://mail.example.com/OAB" -BasicAuthentication $true -RequireSSL $true 
Set-OABVirtualDirectory -Identity "CAS-Server-Name\OAB (Default Web Site)" -InternalUrl "https://mail.example.com/OAB" -BasicAuthentication $true -RequireSSL $true
Set-WebServicesVirtualDirectory -Identity "CAS-Server-Name\EWS (Default Web Site)" -BasicAuthentication $true -ExternalUrl https://mail.example.com/EWS/exchange.asmx 
Set-WebServicesVirtualDirectory -Identity "CAS-Server-Name\EWS (Default Web Site)" -BasicAuthentication $true -InternalUrl https://mail.example.com/EWS/exchange.asmx
Set-ClientAccessServer -Identity "CAS-Server-Name" -AutodiscoverServiceInternalUri https://mail.example.com/autodiscover/autodiscover.xml

Open in new window

You may also need to change the "(Default Web Site)" to match what is shown in IIS, if you have that customized.
Your issue is related to URL, one you sort it out your issue would be resolved. Please refer to this article:

Creating Active Directory Users from a Text File

If your organization has a need to mass-create AD user accounts, watch this video to see how its done without the need for scripting or other unnecessary complexities.

Mahesh SharmaCommented:
jconklin-ansinc-netAuthor Commented:
amit_gokharu: Thank you. I have already followed that article, and communicated in my initial question. Still does not work as expected and the users are still receiving the Security Alert.

jrhelgeson: Thank you. I tried your solution, replacing "mail.example.com" with the URL for the Exchange servers name indicated as the common name on the SSL certificate. Still receive the Security Alerts.

Mks_: Thank you, but your solution does not address the issue we are dealing with. We are not receiving a message about redirection, but a security alert "The name on the security certificate is invalid or does not match the name of the site" when indeed it does.
Okay then, I need the exact error message they get regarding the SSL certificate.
Does the SSL Cert they are getting an error on match the certificate you purchased?

What can happen with Autodiscover is that it can find sites with no relation to yours. Your exchange server is mail.example.com, but it'll throw an SSL Certificate warning/error for www.someothercompany.com.

Please let me know if this is the case, and what the exact error message is.
jconklin-ansinc-netAuthor Commented:
jrhelgeson: Attached are the error messages, the certificate screenshot and a screenshot showing the SANs.
This certificate does not have a private key.

Please speak to the vendor who issued you the certificate, get a cert with private key and then install the same on your exchange 2010 and assign the services which will resolve your issue.
The error message shown in error.png shows 'exchange.domain-name.com'
However, the certificate you purchased does not have 'exchange.domain-name.com' in the SAN field.

You need to change your exchange server so that it no longer points to exchange.domain-name.com

You need to check your dns for service records that point to exchange.domain-name.com, get rid of cname records, A records, SRV records, all on down the line.  Then make sure you ran the commands I provided above with 'mail.domain-name.com' and not 'exchange.domain-name.com'.

That should then work.

Experts Exchange Solution brought to you by

Your issues matter to us.

Facing a tech roadblock? Get the help and guidance you need from experienced professionals who care. Ask your question anytime, anywhere, with no hassle.

Start your 7-day free trial
It's more than this solution.Get answers and train to solve all your tech problems - anytime, anywhere.Try it for free Edge Out The Competitionfor your dream job with proven skills and certifications.Get started today Stand Outas the employee with proven skills.Start learning today for free Move Your Career Forwardwith certification training in the latest technologies.Start your trial today

From novice to tech pro — start learning today.