In part 1, I talked about how we were able to use Google’s servers for SMTP without SSL, so that our firewall appliance would be able to send logs and notifications.

The upside to the approach in part 1 is that it required nothing but using a different SMTP server name and port. The downsides, however, are that the messages are being sent over the wire “in the clear” (unencrypted), and that the account being used to send mail doesn’t record the outgoing messages in its Sent Mail folder (which is handy for confirming that messages are being sent, if there is a problem with receiving them).

So, for the next network-enabled device that we encountered that lacked SSL support for SMTP, I took a different route.

On an internal server, I set up stunnel – an SSL tunneling proxy. With it, I was able to make this server act as a go-between for this networked device and Google’s SSL-requiring SMTP server.

Here’s the relevant section of the stunnel.conf file, which creates port 225 on the server and establishes the SSL tunnel to Google’s SMTP server:

# in /etc/stunnel/stunnel.conf
accept = 225
connect =

On the device doing the sending, I filled in all configuration settings as normal for using Gmail’s SMTP (authentication, etc), but changed the SMTP server address to my tunneling server’s IP address on our internal network, and set the port number to the port I opened with stunnel (225, in the above instance).

I fired up the stunnel daemon on the server, and the SSL-challenged device was able to send mail at will. It was pretty surprising how relatively painless the setup was (the only issue I encountered was the stunnel.conf being very touchy about syntax), and how transparent the solution was once in place. Frankly, I forget that it’s there until I do something else on that server and see the daemon running.

So, there’s another solution for using Gmail/Google Apps’ SMTP service on non-SSL capable devices. This one requires a server to be online and running the stunnel daemon at all times that you want the ability to send mail, but you regain the benefit of having your outgoing mail going over the wire from you to Google through an encrypted connection.