E-mail sending not working after upgrade

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Here are four runs within Docker:

root@foo-app:/# openssl s_client -connect mail.foo.com:587 -starttls smtp
CONNECTED(00000003)
139861698753664:error:1425F102:SSL routines:ssl_choose_client_version:unsupported protocol:../ssl/statem/statem_lib.c:1922:
---
no peer certificate available
---
No client certificate CA names sent
---
SSL handshake has read 320 bytes and written 353 bytes
Verification: OK
---
New, (NONE), Cipher is (NONE)
Secure Renegotiation IS NOT supported
Compression: NONE
Expansion: NONE
No ALPN negotiated
Early data was not sent
Verify return code: 0 (ok)
---
root@foo-app:/#
root@foo-app:/#
root@foo-app:/# openssl s_client -connect mail.foo.com:587 -starttls smtp -tls1_1
CONNECTED(00000003)
140427988595840:error:1425F102:SSL routines:ssl_choose_client_version:unsupported protocol:../ssl/statem/statem_lib.c:1922:
---
no peer certificate available
---
No client certificate CA names sent
---
SSL handshake has read 320 bytes and written 174 bytes
Verification: OK
---
New, (NONE), Cipher is (NONE)
Secure Renegotiation IS NOT supported
Compression: NONE
Expansion: NONE
No ALPN negotiated
SSL-Session:
    Protocol  : TLSv1.1
    Cipher    : 0000
    Session-ID:
    Session-ID-ctx:
    Master-Key:
    PSK identity: None
    PSK identity hint: None
    SRP username: None
    Start Time: 1568985038
    Timeout   : 7200 (sec)
    Verify return code: 0 (ok)
    Extended master secret: no
---
root@foo-app:/#
root@foo-app:/#
root@foo-app:/# openssl s_client -connect mail.foo.com:587 -starttls smtp -tls1_2
CONNECTED(00000003)
140184139936896:error:1425F102:SSL routines:ssl_choose_client_version:unsupported protocol:../ssl/statem/statem_lib.c:1922:
---
no peer certificate available
---
No client certificate CA names sent
---
SSL handshake has read 320 bytes and written 258 bytes
Verification: OK
---
New, (NONE), Cipher is (NONE)
Secure Renegotiation IS NOT supported
Compression: NONE
Expansion: NONE
No ALPN negotiated
SSL-Session:
    Protocol  : TLSv1.2
    Cipher    : 0000
    Session-ID:
    Session-ID-ctx:
    Master-Key:
    PSK identity: None
    PSK identity hint: None
    SRP username: None
    Start Time: 1568985044
    Timeout   : 7200 (sec)
    Verify return code: 0 (ok)
    Extended master secret: no
---
root@foo-app:/#
root@foo-app:/#
root@foo-app:/# openssl s_client -connect mail.foo.com:587 -starttls smtp -tls1_3
CONNECTED(00000003)
write:errno=0
---
no peer certificate available
---
No client certificate CA names sent
---
SSL handshake has read 262 bytes and written 278 bytes
Verification: OK
---
New, (NONE), Cipher is (NONE)
Secure Renegotiation IS NOT supported
Compression: NONE
Expansion: NONE
No ALPN negotiated
Early data was not sent
Verify return code: 0 (ok)
---
root@foo-app:/#

I’m am seeing an error message “protocol unsupported” when forcing TLS other than 1.3 (using additional arguments to the openssl command, see below), and “write:errno=0” only when forcing TLS 1.3. With your command (not forcing TLS) I’m not seeing any specific version being used/attempted.

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