https://bugs.exim.org/show_bug.cgi?id=2104
--- Comment #1 from Jeremy Harris <jgh146exb@???> ---
Up until 4.89 using a continued-TCP-connection for TLS involves dropping
the TLS (in the old transport process) and starting up a new TLS connection
on the same TCP connection in the new transport process (you should be able
to see that sequence in the debug trace).
I'm not sure whether or not the 1.0.2 OpenSSL version is relevant, but it
does appear to be the new TLS startup that's the problem.
Testcase 2113 ("TLS client: multiple messages over one connection")
in the testsuite looks relevant - and that appears to be passing on your
buildfarm machine, which has 1.0.2k. Are you in a position to compare debug
output of that vs. your failing case?
Possibly another direction of investigation would be a packet capture of
a failing case, looking specifically at the TLS startup sequence after that
second STARTTLS.
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