I currently cannot use encrypted email when sending mail via a talktalk smtp server (smtp.talktalk.net).
Firstly port 25 does not support STARTTLS.
Secondly port 587 supports STARTTLS, but requires the FROM field in the mail data to be the same as the talktalk email address used for authentication.
Please can you update port 25 to accept STARTTLS
or
update port 587 to allow specification of aliases for the talktalk email address used for authentication.
I use a custom email address domain which forwards to my talktalk mail domain.