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Re:Show HN: OpenBSD Email Service – A free-email alternative by tux1968 on Saturday February 17, 2018 @01:46AM (#16399419)
You're transiting over their network anyway -- the jig is already up even without relaying via their gateway.
Re:Show HN: OpenBSD Email Service – A free-email alternative by justinclift on Saturday February 17, 2018 @03:16PM (#16402484)
Connecting directly to the remote (non-ISP) mailserver with TLS shouldn't reveal any message contents.

Relaying via the ISP's mail server though (even with TLS) seems like it would disclose the message contents.