UGH! Entourage 2008 and SSL Certificates

I know I'm doing something wrong but I can't get this setup correctly. I'm
ripping my hair out.

I have a SBS2008 server with Exchange 2007 on it with a Godaddy certificate
(remote.domain.com) installed (in keychain's login section) and the
intermediate certificate as well installed all working for IMAPS and RPC
over HTTPS for Outlook 2003/2007. I setup Entourage 2008 with Exchange on a
10.5.6 macmini in the following manner and all is working:
http://blog.dastrup.com/?p=58 (I used the FQDN (remote.domain.com) for
LDAP/HTTPS/Public Folder locations)

However setting up the fscking certificates is not working for me. I did
this for the last job and it was a no brainier but I guess since I'm using a
SBS 2008/Exchange 2007, Entourage 2008 and OSX 1.5 instead of Exchange
2003/Entourage 2004 and OSX 10.4 everything I know to work is thrown out the
window.

I followed the instructions from the Help option when I get the "Can not
establish secure connection...." error message. I double clicked on the
intermediate certificate and installed it into the login second and click
OK. I then installed the remote.domain.com certificate and put it also into
the login section. It never prompted me for my credentials or to ever trust
it (I guess since it was valid and the intermediate cert was there). I
closed keychain. Entourage bitched. I closed Entourage.

I went into my login keychain and set them all (2x Intermediates and the
remote.domain.com certs) to Always trust and gave my password. Closed
keychain and relaunch Entourage. It bitched about the same thing.

I hit up https://remote.domain.com/exchange/username@xxxxxxxxxx and confirm
that it is actually giving out the remote.domain.com certificate with no
error so...what the fsck.


.

Relevant Pages

  • Re: 2008; Certificate problems
    ... Have never setup a certificate, using Intermedia.net as an Exchange 2007 provider, no problem with Entourage 2004, or 2008. ... The Exchange server SSL certificates ...
    (microsoft.public.mac.office.entourage)
  • Re: Entourage 2004 and Exchange 2003: Getting rid of that Root Certificate Warning
    ... The certificate is titled SERVER.COM. ... .COM, but when I change the Exchange Server name, Entourage will re-download ...
    (microsoft.public.mac.office.entourage)
  • Re: can I ignore root certificate error?
    ... > Entourage and Exchange. ... > root certificate installed when I launch Entourage 2004? ... Clicking on it will install the details into your keychain. ...
    (microsoft.public.mac.office.entourage)
  • Re: Root Certificate
    ... > certificate is not installed issue and Entourage won't connect to Exchange. ... > Would a host name mismatch in the certificate terminally affect Entourage to ...
    (microsoft.public.mac.office.entourage)
  • Re: Problems logging into Exchange account with Mac clients
    ... Once I login through OWA then Entourage ... I suspect it is an exchange issue because with the same software ...
    (microsoft.public.mac.office.entourage)
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