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Emails sent from Outlook 2016 are unencrypted - " did not encrypt this message"

Level 2

My mother is using a tpg email that she has owned for quite some time - as emails aren't stored on the TPG server forever, she relies on this account's connection with outlook to keep a copy of her emails.


I realised recently that emails sent from her for the past 2-3 years are unencrypted. My personal email account gives me this warning " did not encrypt this message" for any email sent from her when she uses Outlook.


Note, that if I send an email from the TPG online post office, it is encrypted with TLS/SSL.


It seems that when Outlook connects to the TPG mail server, incoming emails are encrypted with TLS/SSL, but outgoing mail is not. When I try to enable TLS/SSL encryption for outgoing mail, Outlook fails to setup the account. I change these settings in outlook by selecting File > Account Settings > Click her Account > Repair, and then ticking the below options.


I've seen other forum posts about this issue, however they seem to be related to TPG outages and not our connection setup.


I've attached two screenshots - the current connection settings the account uses, and what happens when I try and enable TLS/SSL encryption for outgoing mail.


Please let me know what I need to do to ensure these emails are encrypted.


Hi @em123 . For outgoing mail, try port 25 or 587 with STARTTLS option, if Outlook has it.

Or, port 465 with SSL/TLS.


Level 2

Thanks for the info. It looks like that allowed me to set up the connection with both TLS/SLL and STARTTLS, however when I send myself a test email to my person email (which is a gmail account), I still get the unencrypted warning - " did not encrypt this message". For now, I'll leave TLS/SSL as the selected option as it seems to be the most secure.


Is there anything else I need to do to make sure this is encrypted?