Update: after a lot of discussion with Mitch Burton on the Landscape
team, he was able to demonstrate this working with a self-signed
certificate. We think that this may actually not be strictly an issue
with the self-signed SSL, but rather that the name in the cert is not an
FQDN, and instead is just the bare hostname.

Upon further testing myself, I swapped the hostname on my test instance
from landscape-2310-jammy to landscape-2310-jammy.lxd just as a test. I
then updated my /etc/hosts file, the certificates configured in Apache,
and imported the newly generated cert into ca-certificates. After this
dput worked just fine.

dput lds:ubuntu/jammy/upload hello.changes

D: Splitting host argument out of  lds:ubuntu/jammy/upload.
D: Setting host argument.
Checking signature on .changes
gpg: /root/hello.changes: Valid signature from 5E1E964200F3EA3D
Uploading to lds (via https to landscape-2310-jammy.lxd):
  Uploading hello_2.10-2ubuntu4+esm1_amd64.deb: done.  
  Uploading hello.changes: done.
Successfully uploaded packages.

This seems to confirm that the issue is not necessarily with dput
directly, but in how python's urllib is checking the domain/cert on the
connection. This may be something that can be worked around in dput to
allow for a bare hostname that is not an FQDN, but either way figured it
would be relevant to add this information.

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https://bugs.launchpad.net/bugs/2055450

Title:
  Uploading package to server with self-signed certificate on https
  fails despite adding cert to trust-store

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