UGH! Entourage 2008 and SSL Certificates

[Nathaniel]

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/[email protected] and confirm
that it is actually giving out the remote.domain.com certificate with no
error so...what the fsck.

 

[Corentin Cras-Méneur]

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.

It looks to me like you imported the SSL certificates, but not the root
certificate required for e-mails.
I believe other people reported the same thing here before and once they
installed the proper root certificate for GoDaddy, the problem went
away,


Corentin

 

[Nathaniel]

From the Certificate manager in office or keychain I can follow the
certificates back to the root www.valicert.com. I have all the certs
required.

 

[Corentin Cras-Méneur]

From the Certificate manager in office or keychain I can follow the
certificates back to the root www.valicert.com. I have all the certs
required.

Are you sure the cert is valid *for your mail server*??
They have a page full of certificates:
http://certificates.godaddy.com/repository

Are you sure you picked the right one??

I don't doubt that the certificate you have is valid. I just suspect it
doesn't cover the server you are trying to connect to.


Corentin