Yes!

For PingPlotter:

PingPlotter uses OpenSSL to do STARTTLS conversations. In PingPlotter, we don't ship this, by default, because of the low demand for this option, plus the fact that it would add around 550kb to the install.

If you need STARTTLS support to send email, download this file:

http://www.nessoft.com/downloads/OpenSSL098g.zip

Once downloaded, extract the contents of this archive to your PingPlotter install directory (example: for PingPlotter Pro, this might be "c:\Program Files\PingPlotter Pro\").

Now, go to Edit -> Options, Email Setup. You'll see a new option for "Use STARTTLS encryption if server supports it". Turn on that option. Don't forget to change your SMTP server port (probably 465 or 587).

If you're using GMail, follow the instructions from GMail to set the right port, username, password and SMTP server as well.

If you have any problems or questions, please contact us at support@nessoft.com.

Note that this requires PingPlotter Standard 3.20.1s or higher, or PingPlotter Pro 3.20.1s or higher.

For MultiPing:

MultiPing starting with version 2.10.0 has support for STARTTLS built into the installer.

Go to Edit -> Options, Email Setup. You'll see an option for "Use STARTTLS encryption if server supports it". Turn on that option. Also, make sure you change the SMTP server port to match your server's needs (probably 465 or 587).

If you're using GMail, follow the instructions from GMail to set the right port, username, password and SMTP server as well.