SSL on virtual SMTP and Apple

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    Dear all,

    I’m running an Exchange 2003 with a virtual SMTP server listening on port 465 behind a firewall with a chained SSL certificate from Comodo. With “Require secure channel” un-checked (not using SSL), I am able to send out emails using Apple Mail 4.0 on port 465 but with it checked, the process just times out. However, I can send out emails with “Required secure channel” turned on using Thunderbird.

    I also generated a self-signed certificate using the server’s internal name and attached it to the virtual SMTP server and still would just time out but no problem with Thunderbird.

    Hope you can help me troubleshoot this issue.

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