Starttls, in both SMTP and IMAP, can be mitm'd (injection of refusal). We 
should not be using them any more.
Paul Vixie

Feb 26, 2026 17:57:47 John R Levine <[email protected]>:

> On Wed, 25 Feb 2026, Dan Wing wrote:
>> One approach would be take idea of 
>> https://datatracker.ietf.org/doc/html/rfc8314 and extend it include SMTP 
>> itself, which would bring QUIC along doing a happy eyeballs-like attempt at 
>> QUIC falling back to TLS-over-TCP falling back to TCP-port-25-STARTTLS 
>> falling back to TCP-port-25 plaintext, or as Martin suggested have DNS 
>> optimize those choices.
> 
> The problem with that is that SMTP doesn't do the TLS handshake at startup, 
> only after a STARTTLS command in the TCP session.  But see next message.
> 
> R's,
> John

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