ECTool is very nice shareware application for the email-chess player. Worth mentioning that while it is Windows program, it works without any problems under Linux (using wine emulator).
Article below explains how to use ECTool with email server, which require SSL connection (not handled by ECTool itself).
Download stunnel
Download stunnel (it is easiest to use precompiled windows binary) and install it.
Configure stunnel
Edit stunnel.conf file using any text editor (there even is link to open this file in created Start menu folder). For the purpose of using ECTool it should contain:
; Some performance tunings
socket = l:TCP_NODELAY=1
socket = r:TCP_NODELAY=1
; Use it for client mode
client = yes
; Service-level configuration
[pop3s]
accept = 110
connect = my.pop3.server:995
[ssmtp]
accept = 25
connect = my.smtp.server:465
Remember to replace my.pop3.server and my.smtp.server with the name of email server you use. In case it uses non-standard ports, replace 995 and 465 with those ports.
Finally, select Service install option from the stunnel start menu folder, follow it with Service start. Stunnel will be running as window service, providing SSL to your email connections.
Configure ECTool
In the ECTool configuration window enter localhost as both SMTP and POP3 Server. Enter your normal username and password where needed. In case your mail server does not use SSL-enabled SMTP, you can enter normal SMTP address, leaving only POP3 directed to localhost.
Test whether everything work - download your email, create some test message and send it to yourself. And enjoy.
How does it work?
Simple. When you want to download email, ECTool connects to port 110 (POP3 port) on your own computer (localhost). Stunnel listens on this port and whenever something connects here, it creates SSL connection to configured place (here, your real mail server). So, for ECTool it looks like there is non-SSL mail server on loal machine, at the same time for your mail server it looks like SSL-enabled client is connecting.