I use a mail client that does not directly support SSL. I can use stunnel to provide the security layer when I connect to a SSMTP and/or POP3S server (under windows). This works fine, whether I run stunnel as a background application or as a Windows service.

I'd like, however, to be able to connect to multiple mail servers over SSL. I'm not sure how I might achieve this?

What would be nice would be get stunnel to forward POP3/SMTP communication on different local ports to POP3S/SSMTP on different remote servers. Can I do this?

It appears to be possible to run multiple copies of stunnel as applications, and to get each copy to take its configuration from a different stunnel.conf file, so that different copies of stunnel could listen on different local ports and each could proxy the traffic it receives to a different remote server (I haven't tried this -- and it's not an ideal solution -- but it looks as though it should work).

It does not appear to be possible, however, to create two instances of the stunnel service running with different configuration files.

Is it possible to set up multiple listening ports proxying to different remote servers in a single configuration file? If so, what's the syntax for that?

Cheers, Daniel.