this post is obsolete
see:
Using Gmail SMTP
Using Office365 SMTP
Using SendSMTPMail
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.
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 that some email servers (notably send.xtra.co.nz) require you to specify port 587 (this port accepts an initial unencrypted connection that uses the STARTTLS protocol to start encryption; The xtra website specifies port 465, but neither this port, nor the default SMTP port 25 will work with sendemail). Specify the server address as send.xtra.co.nz:587.
smtp.google.com will accept a connection on port 25 and negotiate encryption, so you do need need to specify the port as part of the server name.
Update
As of v7.1.8, SendEmail is included in the standard install on Windows as well as Mac