Hi Rajeev,

That seems to be due to a bogus cert chain on the server side. One of the intermediate expired recently, see the "Not After":

https://letsencrypt.org/certs/lets-encrypt-x3-cross-signed.txt

Presumably Thunderbird is a bit more forgiving and uses another chain of trust but msmtp's TLS stack doesn't.

Another confirmation https://www.hardenize.com/report/smtp.sivalik.com/1616099988#email_certs

HTH,
Simon

On 2021-03-18 3:02 p.m., Rajeev wrote:
Package: msmtp
Version: 1.8.11-2
Severity: normal

Dear Maintainer,

I am able to talk to the smtp server at smtp.sivalik.com:587 to submit email
using thunderbird but msmtp gives error that the certificate has expired. I
have confirmed that the certificate is valid.

I tried to debug using openssl s_client and for the case where msmtp works
(gmail) and the case for which it does not (sivalik). I found that sivalik
server sends a post handshake new session ticket, which msmtp does not seem to
  handle and gives an incorrect error description.

-- System Information:
Debian Release: bullseye/sid
   APT prefers testing
   APT policy: (990, 'testing')
Architecture: amd64 (x86_64)
Foreign Architectures: i386

Kernel: Linux 5.10.0-4-amd64 (SMP w/4 CPU threads)
Locale: LANG=en_US.UTF-8, LC_CTYPE=en_US.UTF-8 (charmap=UTF-8), LANGUAGE not set
Shell: /bin/sh linked to /usr/bin/dash
Init: systemd (via /run/systemd/system)
LSM: AppArmor: enabled

Versions of packages msmtp depends on:
ii  adduser                3.118
ii  debconf [debconf-2.0]  1.5.75
ii  libc6                  2.31-9
ii  libgnutls30            3.7.0-7
ii  libgsasl7              1.10.0-4
ii  libsecret-1-0          0.20.4-2
ii  ucf                    3.0043

Versions of packages msmtp recommends:
ii  ca-certificates  20210119

Versions of packages msmtp suggests:
ii  msmtp-mta  1.8.11-2

-- Configuration Files:
/etc/apparmor.d/usr.bin.msmtp changed [not included]

-- debconf information excluded


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