On Sat, Sep 29, 2007 at 05:23:29PM -0500, Robert Lambrecht wrote:

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.

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.

stunnel is listening on port 25 *of your machine*, not your isp's. Thus, you need to have BLAT send it to localhost, port 25.

Better yet, to avoid confussion, have stunnel listen on some other port (456 would be a good choice), and have BLAT send to localhost, on that port.

To check you're not sending anything on the clear, install a network sniffer (wireshark is good) and have it show your network trafic to your.isp.com. If you can read the mail in the displayed traffic, you're sending in cleartext ;-)