I'm stumped on this and can use some help. How could I configure an SMTP relay on a Windows 2000 Pro, 2000 Server, or XP Pro machine which is configured on a workgroup? I have an application which can send email out via SMTP, but does not support SSL encryption. Is it possible for me to configure an SMTP server in the above operating systems, to listen for outbound email on port 25, and to relay those to an SSL SMTP remote server? From what I have been able to gather, this is not possible in Vista. I recently experienced it being done in a Windows 2003 Standard Server domain environment which prompted me to ask this question.
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