OK. After much frustration I finally have Entourage making an SSL connection to an Exchange server in Mac OS X Leopard after performing the OS installation from scratch.
All that is needed is your root certificate - no private key, no digital identity, no microsoft intermediate junk or any of that hullabaloo - just the root certificate only.
Now do the following:
1. Put the root certificate in your home folder.
2. Open a terminal.
3. Type the following:
sudo certtool i root_certificate.cer v k=/System/Library/Keychains/X509Anchors
Obviously replacing "root_certificate.cer" with your certificate filename.
The last line of output should read "...certificate successfully imported." If you get an error saying that the certificate is in the wrong format and needs to be in PEM format, then use the Microsoft Cert Manager to convert the certificate format by importing then exporting as PEM.
Ha - beat ya Microsoft! I'm a single guy that fixed this. You're a massive company with squillions of $$$ and hundreds if not thousands of people and you can't even fix this after 1 week! Why exactly should people buy or even use your crappy products for OUTRAGEOUS prices!?!?!!?
C'mon people, try get your boss / IT administrator etc. to switch to something else, preferably supporting an open standard file format - that way no-one will ever be tied down to using a particular vendors product.
Why did it break?
As it turns out, the X509Anchors file, as of Leopard, has been made obsolete - but not entirely... It can (and is) still read from, but cannot be written to - at least not with any GUI interface like Apple Keychain or Microsoft Cert Manager.
As Entourage looks at this X509Anchors file for the Root Certificate and not in the new SystemCA/RootCertificates.keychain files, of course it's not going to find it! This also explains why people that upgraded rather than fresh installed did not encounter this age old problem again.
So Microsoft, if you're still in the complete darkness and have no clue what i'm going on about, to fix this problem from your end, send out an update that makes Office for Mac look in the SystemCACertificates.keychain and SystemRootCertificates.keychain files for root certificates and don't remove the parsing of the X509Anchors file just yet either or you'll break it again! People need time to make the switch...
All that is needed is your root certificate - no private key, no digital identity, no microsoft intermediate junk or any of that hullabaloo - just the root certificate only.
Now do the following:
1. Put the root certificate in your home folder.
2. Open a terminal.
3. Type the following:
sudo certtool i root_certificate.cer v k=/System/Library/Keychains/X509Anchors
Obviously replacing "root_certificate.cer" with your certificate filename.
The last line of output should read "...certificate successfully imported." If you get an error saying that the certificate is in the wrong format and needs to be in PEM format, then use the Microsoft Cert Manager to convert the certificate format by importing then exporting as PEM.
Ha - beat ya Microsoft! I'm a single guy that fixed this. You're a massive company with squillions of $$$ and hundreds if not thousands of people and you can't even fix this after 1 week! Why exactly should people buy or even use your crappy products for OUTRAGEOUS prices!?!?!!?
C'mon people, try get your boss / IT administrator etc. to switch to something else, preferably supporting an open standard file format - that way no-one will ever be tied down to using a particular vendors product.
Why did it break?
As it turns out, the X509Anchors file, as of Leopard, has been made obsolete - but not entirely... It can (and is) still read from, but cannot be written to - at least not with any GUI interface like Apple Keychain or Microsoft Cert Manager.
As Entourage looks at this X509Anchors file for the Root Certificate and not in the new SystemCA/RootCertificates.keychain files, of course it's not going to find it! This also explains why people that upgraded rather than fresh installed did not encounter this age old problem again.
So Microsoft, if you're still in the complete darkness and have no clue what i'm going on about, to fix this problem from your end, send out an update that makes Office for Mac look in the SystemCACertificates.keychain and SystemRootCertificates.keychain files for root certificates and don't remove the parsing of the X509Anchors file just yet either or you'll break it again! People need time to make the switch...
