Ok, thanks for the suggestion there Dimitri.

I ran a wireshark to see what happened when I pinged the hostname which
would inevitably fail, and I got nothing in wireshark. What I think is
happening and makes most sense is that the stub resolver is eating up my
DNS lookup and not forwarding it onto my nameserver. This is why there
is no network traffic for the ping as the resolve just fails inside the
stub resolver.

Is the nsswitch.conf a clue here?

hosts: files mdns4_minimal [NOTFOUND=return] dns

Does that mean that if there is not hostname found, it returns and not
forwards to dns?

After the failed wireshark, I switched the /etc/resolv.conf to not point
to the stub-resolv.conf and all is well again.

I would still like to help fix this issue though.

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https://bugs.launchpad.net/bugs/1779438

Title:
  Cannot resolve names using systemd-resolved stub resolver

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