SYMPTOM:
When configuring Strategy Distribution Services to use an SMTP server that requires a TLS connection (such as Google's public SMTP server), emails will are not delivered. Testing the SMTP server by manually sending the email through telnet also does not work, producing the following error: Must Issue a STARTTLS command first.

220 mx.google.com ESMTP 16sm8159642fxm.8 ehlo smtp.google.com 250-mx.google.com at your service, 250-SIZE 35651584 250-8BITMIME 250-STARTTLS 250-ENHANCEDSTATUSCODES 250 PIPELINING mail from:xxx.xxxx@gmail.com 530 5.7.0 Must issue a STARTTLS command first. 16sm8159642fxm.8