Strange as "openssl s_client -starttls smtp -connect mail.cvut.cz:587" works for me, can you try that yourself in case there's any different config for local clients and that fails for you? (It's also possible they have fixed the server by now :-)

LibreSSL doesn't support SSL, only TLS, so attempts to set SSLv2/3 won't do what you want for sure.

Compiling against OpenSSL is tricky, you have to make sure it uses the correct headers (and sometimes relevant you have to avoid linking against any library that uses LibreSSL).

--
 Sent from a phone, apologies for poor formatting.
On 29 August 2020 18:59:41 Jan Stary <h...@stare.cz> wrote:

This is mutt-1.14.6v3-sasl in 6.7-current/amd64.
Recently, my institution's mail has been moved to
220 mail.cvut.cz Microsoft ESMTP MAIL Service

Trying to send mail through it fails with

SSL failed: error:1404B42E:SSL routines:ST_CONNECT:tlsv1 alert protocol version

I enabled all the following to also enable the older ssl/tls protocols
in case the server needs one that is not enabled by mutt by default
as "tlsv1 alert protocol version" would suggest:

set ssl_starttls  = yes
#set ssl_force_tls = yes
set ssl_use_sslv2 = yes
set ssl_use_sslv3 = yes
set ssl_use_tlsv1 = yes
set ssl_use_tlsv1_1 = yes
set ssl_use_tlsv1_2 = yes
set ssl_use_tlsv1_3 = yes

It made no difference, the error message is the same.

What's strange is that when connecting to the same server via IMAP
(to read mail as opposed to send mail), mutt reports

TLSv1.2 connection using TLSv1/SSLv3 (ECDHE-RSA-AES256-GCM-SHA384)

and I can read my INBOX; that makes me think
that ssl/tls connections to the server generally work.

After rebuilding mutt from source --with-gnutls instead of --with-ssl,
(and checking with ldd that it is indeed linked against gnutls and
not linked against libssl and libtls), the error becomes

gnutls_handshake: An unexpected TLS packet was received.

Suspecting that the server might be discriminating on the
exact version string (if there is such a thing), I also tried
to compile against the openssl port, i.e. the ssl/tls in /usr/local,
but I couldn't do it: the mutt build system alwasy picks the lib
in /usr/lib, whoch is LibreSSL, not OpenSSL.

Can I debug the details of the attempted tls connection?
(Recompiling --with-debug and running with -d 10 doesn't reveal anything.)

Is anyone seeing the same?

Jan


FWIW, with NetBSD's Mutt 1.11.4 (2019-03-13), the error is
SSL failed: error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown protocol

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