Entourage 2008 has a pop up about unable to establish a secureconnection

[Alison.L.Murphy]

We click ok and can use the client but can't stop this pop up from
happening.

The error is "Unable to establish a secure connection to Heroix.com
because the server name or IP address does not match the name the name
or the IP address on the server's certificate."

Heroix.com is our domain name and we have a certificate for
exchange.heroix.com, autodiscover.heroix.com and then our internal
names for our exchange server. These certificates are on our exchange
server. We also tried putting some certificates on the mac after
reading some articles online about it. Nothing is working...

Any thoughts?

 

[Diane Ross]

The error is "Unable to establish a secure connection to Heroix.com
because the server name or IP address does not match the name the name
or the IP address on the server's certificate."

Heroix.com is our domain name and we have a certificate for
exchange.heroix.com, autodiscover.heroix.com and then our internal
names for our exchange server. These certificates are on our exchange
server. We also tried putting some certificates on the mac after
reading some articles online about it. Nothing is working...

My understanding it has something to do with the certificate. As of SP1,
Entourage looks for the AutoDiscover xml file. If you take a look in the
Exchange 2007 AutoDiscover whitepaper, you'll see it uses two URLs to look
for the autodiscover xml file. Both URLs are based off your SMTP address in
your email address - it doesn't matter what server you connect to.

You can take a look at the AutoDiscover whitepaper here:
http://technet.microsoft.com/en-us/library/bb332063.aspx

Here is an example for Joe Blow.

In this case, all email addresses from Joe's server end with @blow.net. This
means we will connect to autodiscover.blow.net and blow.net looking for the
xml file. If Joe's server happened to host another email domain and gave out
email addresses ending in @joesfriends.com, then Entourage would connect to
autodiscover.joesfriends.com and joesfriends.com looking for the
Autodiscover xml file. The actual urls that we connect to in this case are:

https://autodiscover.blow.net/autodiscover/autodiscover.xml
https://blow.net/autodiscover/autodiscover.xml

Since the first one doesn't exist (no DNS record), we try the second one.
But the cert at that the second location does not have "Blow.net" on the
cert, thus you get a host name mismatch error and Entourage shows the
dialog.

The fix in this case would be to:

1) Add Blow.net to the cert located at: https://blow.net

2) Create a DNS record for autodiscover.blow.net and point it at the same
server as rapier.blow.net as well as add autodiscover.blow.net to the
certificate as well as rapier.blow.net.

Let me know if this helps.