This situation is somewhat unique and maybe it's too much work for to little gain but it was a situation I couldn't solve in a simpler way. Maybe someone will shine some light on me.
Problem
The problem I had was to enable the emailing features of a instance Bugzilla which is installed on a Windows 2000 machine behind a proxy server. I wanted to use a external email account (in this case a gmail account) to send all bug email messages.
Approach
Having not found a piece of software that managed this I' decided for the complex approach which was to devide the problem in two parts, the SMTP Authentication and the Proxy Server.
Sending Email with SMTP Authentication
To send all email I'm using Fake Sendmail. This allows me to use a SMTP account with authentication, something that Bugzilla doesn't provide.
In the sendmail.ini file configure 127.0.0.1 as the SMTP Server defined is so all emails are sent through the SMTP tunnel (seen next).
Pass through the Proxy
To pass through the Proxy Server I'm behind I use the mailFISH: Free HTTP tunnel for POP3 and SMTP.
Conclusion
Sendmail connects to the SMTP proxy providing SMTP authentication information which mailFISH doesn't manage and the latter tunnels the request through the HTTP Proxy.
Hopes this helps someone else.
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