I am using a command line mailer (BLAT) from a batch file to notify me when errors occur. My ISP requires SSL however still allows non-SSL traffic on Port 25 as well.

Here is my scenario:

I use BLAT to send an SMTP message on Port 25 to my ISP. This works but I must send my userid and password which I don't want to do.

I then use Stunnel with the following config:

[smtps]

accept = 25

connect = smtp.isp.domain.net:465

Port 465 is the SSL port for my ISP.

I run Stunnel as a service in Vista.

I then have BLAT send an SMTP message on Port 25 to my ISP. This works.

My question is, everything seems to work but how can I test this?

I'm trying to figure out if it really worked (I sent the message with SSL to port 465) or I am still just sending a message on Port 25. Since both of these cases work, it is hard for me to tell.

I've tried to telnet to these ports; however, since I basically have to specify port 25 in either case for the test, I'm not sure that I am successful.

Any thoughts on how to make sure my messages are going through SSL?

Bob