I deployed a fresh resolute vm server, and chrony was installed. I then
changed the date to 2000-01-01, which would make it impossible to use
NTS with the standard servers.

And indeed it complains about the *standard* server (not the bootstrap
one):

Jan 01 00:00:00 r-chrony systemd[1]: Started chrony.service - chrony, an NTP 
client/server.
Jan 01 00:00:00 r-chrony chronyd[4429]: Added pool 1.ntp.ubuntu.com
Jan 01 00:00:00 r-chrony chronyd[4429]: Added pool 2.ntp.ubuntu.com
Jan 01 00:00:00 r-chrony chronyd[4429]: Added pool 3.ntp.ubuntu.com
Jan 01 00:00:00 r-chrony chronyd[4429]: Added pool 4.ntp.ubuntu.com
Jan 01 00:00:00 r-chrony chronyd[4429]: Added pool ntp-bootstrap.ubuntu.com
Jan 01 00:00:02 r-chrony chronyd[4429]: TLS handshake with 185.125.190.122:4460 
(1.ntp.ubuntu.com) failed : Error in the certificate verification. The 
certificate is NOT trusted. The certificate chain uses not yet valid 
certificate.
Jan 01 00:00:06 r-chrony chronyd[4429]: Selected source 91.189.91.113 
(4.ntp.ubuntu.com)
Jan 01 00:00:06 r-chrony chronyd[4429]: System clock wrong by 833292561.695228 
seconds
May 28 14:09:27 r-chrony chronyd[4429]: System clock was stepped by 
833292561.695228 seconds
May 28 14:09:27 r-chrony chronyd[4429]: System clock TAI offset set to 32 
seconds
May 28 14:09:28 r-chrony chronyd[4429]: System clock TAI offset set to 37 
seconds

The error about 1.ntp.ubuntu.com is CORRECT and is what we want. That's
where the ntp-bootstrap.ubuntu.com server comes in, and looks like it
worked, as it should. There is no error referencing it, and the time was
updated.

Could you guys perhaps be missing the /etc/chrony/conf.d/ubuntu-nts.conf
file with the setting "ntstrustedcerts 1 /etc/chrony/nts-bootstrap-
ubuntu.crt"?

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https://bugs.launchpad.net/bugs/2152270

Title:
  nts-bootstrap-ubuntu.crt missing CN=ubuntu CA cert, NTS sync fails on
  fresh install

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