Disable SSL requirement for Outlook clients

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Oliver M

I have an Exchange 2007 server and 2 years ago I ran into the problem that Outlook clients got an SSL certifcate error when trying to connect, due to the difference in the internal and external servername.
I solved this problem by somehow disabling the need to have a SSL certificate on the Exchange 2007 server after which the clients could connect without an error.

I now installed a new Exchange 2010 server and am running into the same problem. How can I disable the SSL requirement to get the same solution?


Using IIS Manager you can remove the require SSL off of the Default Web Site.

In the Features view of the Default Web Site double-click on SSL settings and uncheck the require SSL and click on Apply. This change should propogate down to the other virtual directories.

MCITP: Enterprise Messaging Administrator 2007/2010 | MCITP: Server Administrator | MCTS: Windows Server 2008 Applications Infrastructure, Configuring | MCP | MCDST

Oliver M

Just tried it, but makes no difference.

When a user opens Outlook, they still get the certificate error....


I have to ask the question...why not fix the SSL and configure Exchange the approprate way? Exchange 2010 is designed to work securely in every facet of operation. My advice is to buy a certificate (very cheap) and configure Exchange appropriately.

Jonas Andersson [MCITP]

I agree with Tim, godaddy.com have cheap certificates if you don't want to go for VerisignJonas Andersson MCTS: Microsoft Exchange Server 2007/2010 | MCITP: EMA 2007/2010 | MCSE/MCSA Blog: http://www.testlabs.se/blog

Oliver M

The reason is I really don't understand the use of certificates in Exchange.

- I now have a valid certificate for the IIS service, which assures that the OWA users don't receive a certificate error message. This certificate is isued to mail.externaldomain.com
- I also have a selfsigned certificate for IMAP, POP, SMTP service. This certificate is isued to mail2.internaldomain.com
What do I need to do to assure that Outlook clients won't receive an error message?


So the pop-up you are seeing is for the autodiscover service. Outlook is hardcoded to look for this service with a specific name: autodiscover.smtpdomain.com. The best way to handle this is getting a UC/SAN certificate and including both your mail.externaldomain.com and autodiscover.externaldomain.com. IF you don't want to mess with that, you can get by with a single name certificate, but you need to configure Exchange appropriately and set up some SRV DNS records. This link should help:


Oliver M

The following problem arrises now.

I own a ssl certificate for mail.externaldomain.com, I tried to order a ssl certificate for mail.internaldomain.com but I am not allowed to purchase that because we don't own the *.internaldomain.com.
In order to workaround this problem I changed the autodiscover url to mail.externaldomain.com, and this way the ssl error disappeared, but the clients now have to login everytime they open the Outlook client....
How can I resolve this problem??
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