I want to send mail by DO with smtp.live.com.
But i have an error 530 5.7.0 must issue a STARTTLS command first.
It looks like SSL connection. I am not sure if DO supports this.
You might find stunnel - stunnel.org/ may help - it is free. I needed it to get my email system to talk to my ISP mail servers which changed to using TLS encryption.
Roger