As of v7.1.8, MoneyWorks includes the sendEmail tool as part of the standard install, so TLS support is available on Windows (as well as Mac) out of the box. Blat is also still included, but will no longer normally be used.
Previous version of this FAQ:
The standard MoneyWorks install on Windows includes a tool called blat (http://www.blat.net) for sending emails via an SMTP server. This is used when you select and configure the SMTP email option in MoneyWorks Preferences.
While it is light weight, blat does not support secure TLS connections to SMTP servers (such as smtp.gmail.com) that require them. If you need to send via TLS, you can install sendEmail.exe in the MoneyWorks executable folder. If this tool is detected, it will be used preferentially to blat.
Sendemail is available here: http://caspian.dotconf.net/menu/Software/SendEmail/ . Be sure to get the full binary with TLS support compiled in. Download sendEmail-v156.zip and unzip into (e.g.) C:\Program Files (x86)\MoneyWorks Gold\
BTW, the standard Mac install of MoneyWorks includes the perl version of sendEmail within the MoneyWorks app package, so you don’t need to install anything further to support TLS SMTP on Mac.
Note: Requires MoneyWorks version 7.1.4 or later