Thanks!  stunnel works for me, both in Ubuntu hardy and eeepc default Xandros.  I had hesitated to try it because i didn't understand what it does, and thought it would need to be installed on the mail server.  but that was incorrect; i didn;t need to change anything on the server.   I tried the Linux version sof stunnel on both platforms, and couldn't get them to work with pmail.  But I installed the Windows version of stunnel under wine, configured pmail SMTP to send to 127.0.0.1 and the stunnel input port,  edited the stunnel.conf according to the message quoted above, and commented out the stunnel.conf line for a "key" file.  Run stunnel, then pmail, and it works.

I haven't tried ASSP -- it looks interesting, but more than I need right now.

There is no sign of any progress on the longstanding bug that prevents use of encrypted connections to SMTP servers from Pegasus Mail under wine in Linux:

http://bugs.winehq.org/show_bug.cgi?id=14797

http://appdb.winehq.org/objectManager.php?sClass=version&iId=15815

(If you would like to use pmail in Linux, please *vote* for this bug at the link above.)

In the meantime, the simplest workaround I can think of is to install the smallest and simplest possible local SMTP proxy server that can be configured to use an SSL connection to an external SMTP server, even if pmail is sending to the proxy using unencrypted SMTP.  I only need to use a single SMTP server for all outgoing mail, so that could be configured in the proxy.

Can anyone recommend such a small, simple, SMTP proxy that will work for this purpose?  I don;t want to install an entire large nMTA package, if that can be avoided -- just a simple local SMTP proxy. I'm using Ubuntu and the default Xandros on an Asus eeepc, both of which are Debian-based Linux distributions.  A java proxy would also be feasible, if that would be a more "universal" solution or easier to install.

> In the meantime, the simplest workaround I can think of is to install the smallest and simplest possible local SMTP proxy server that can be
> configured to use an SSL connection to an external SMTP server, even if pmail is sending to the proxy using unencrypted SMTP.  I only need
> to use a single SMTP server for all outgoing mail, so that could be configured in the proxy.

I do use Pegasus Mail and Mercury on Ubuntu and Wine sending/receiving via an SSL connection to the GMail server.  All I do is use STunnel for Windows running via Wine to make the connections.  This process has been described in the answers to this bug http://bugs.winehq.org/show_bug.cgi?id=14797 as a workaround.   

 Comment #16 From  Michael Setzer II   2009-06-04 06:57:47

In my opinion, finding a SMTP Proxy server that can do SSL/TLS would be a lot harder that using this solution.

I highly recommend ASSP (written in perl); it will do as you expect and has the added benefit of off-loading threat control from your MTA. It has breathed new life into our SIMS installation (on Solaris) and I run it on a different host in order to offload the mail server and to permit retaining standard port assignments both on the LAN and from the outside.

I like that idea of using an encrypted tunnel from the wine session to the emulator host too, but ASSP has so many added benefits that I would urge you to try it.

Michael