Exchange 2003 SMTP SSL and various email clients

Posted by FrancisV on Server Fault See other posts from Server Fault or by FrancisV
Published on 2011-06-25T03:02:34Z Indexed on 2011/06/26 8:24 UTC
Read the original article Hit count: 250

Filed under:

ssl

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smtp

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exchange-2003

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apple

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thunderbird

This Exchange 2003 server sits behind a firewall with a virtual SMTP server listening on port 465 and attached an SSL certificate from Comodo to the virtual server. However, when trying to send from Apple Mail.app 4.x and Outlook 2011 for Mac, it never completes the connection (time out). Oddly though, the same setup works with Thunderbird. My question is:

Does it matter if the friendly name of the certificate is different from the internal hostname? The machine has 2 hostnames: external and internal. The official SSL is using the external name.
When using a self-signed certificate with the same name as the internal, I still can't send from the Mail.app and Exchange clients but I can with Thunderbird.

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