Important - As of v188.8.131.52, this is no longer required as Drive Bender handle SSL natively.
When setting up the SMTP server for email notifications, Drive Bender will automatically enable SSL/TLS if either port 587 or 465 is specific.
If you have specified either of these ports and you are receiving the following error "Port 465/587 requires SSL support", your server does not have the required components to create the SSL/TLS connection. There are a number of SSL/TLS packages about, one being the OpenSSL Tool Kit (http://www.openssl.org/).
Installing the OpenSSL binaries.
1) Head to http://www.microsoft.com/en-us/download/confirmation.aspx?id=29 download and install "Microsoft Visual C++ 2008 Redistributable Package (x86)"
2) Head to https://slproweb.com/products/Win32OpenSSL.html, then the "OpenSSL for Windows" link. From here download and install "Win32 OpenSSL vX.X.X Light" (the first item in the list).
Once done, the server should now support SLL/TLS.
Note is you are attempting to connect to the Gmail SMTP server, specify port 465.
Now the legal stuff - The above information is supplied "AS IS", and anyone installing the OpenSSL Toolkit does so at their own risk.