Q&A: how do I fix the "Unable to establish a secure connection ..." issue in Entourage:Mac?

From my open question thread:

When opening my inbox from an Exchange 2007 SP1 server with Entourage 12.2.3 I get a dialog saying "Unable to establish a secure connection to example.com because the correct root certificate is not installed."

There's a few things that you can do to get rid of this dialog.

One option is to ask your admin for a root certificate. After you receive that certificate from your admin, you can install it. If that solves the problem some but not all of the time, open the Microsoft Certificate Manager application (it's in the Office folder) and import the certificate there.

Another option is to uncheck the "This DAV service requires a secure connection (SSL)" box. It's on the Advanced tab in your Account Settings for that Exchange account.

If you're feeling particularly techy, you can check to see if your Exchange server's autodiscover service is set up properly. Amir wrote up some instructions in his blog post SSL warning issue in Entourage 2008. Look down to the note for the instructions that you as a user (and not an Exchange admin) can take to see if it's set up properly. If your autodiscover service isn't set up properly, you can at least inform your Exchange admin about it and ask them to fix it. There's a whitepaper for setting up the Exchange 2007 autodiscover service which has plenty of details for how your Exchange guys can get it set up properly.

For additional troubleshooting without calling Microsoft tech support (for which you get two free calls with your purchase of Office 2008) or any internal tech support that you might have, you might want to try the Entourage public forum.

Comments

• Anonymous
  November 26, 2009
  The comment has been removed

• Anonymous
  November 26, 2009
  Hmmm, let me check with someone else, since you're now past my Exchange expertise.  I doubt I'll get an answer before next week, since some lazy people seem to think that they get both holidays AND weekends off. ;)

• Anonymous
  November 26, 2009
  hmmm...Let me try this one because I am having the same problem "Unable to establish a secure connection" with my server. Thanks!

• Anonymous
  November 30, 2009
  The comment has been removed

• Anonymous
  November 30, 2009
  This discussion in the Entourage support forum is pertinent: http://www.officeformac.com/ms/ProductForums/Entourage/5019 The question is "Is there an override/workaround for manually configuring autodiscover on the client?"

• Anonymous
  December 01, 2009
  The comment has been removed

• Anonymous
  December 02, 2009
  Hello Nathan, In our case the misconfigured server is not providing LDAP or any other Exchange service. It is not the Client Access server. The troublesome domain name is used as an email alias for staff but otherwise has nothing to do with our directory structure. If the order of autodiscover lookups were reversed (i.e. check the most specific entry first, _autodiscover._tcp.example.com) or if there were a way to explicitly set the autodiscover server address or if there were a way to disable the autodiscover behaviour altogether then I could avoid the misconfigured server completely. Autodiscover for our primary domain works perfectly. Having a way to disable or override the autodiscover behaviour would be great.