Maybe it does? It could be serving plaintext HTTP ("why would we encrypt our logo.png file?"), or the client library could be configured to accept any valid SSL cert because they don't want to deploy good certs to every ephemeral host they spin up.
Agreed. In my mind, if the server is using plain HTTP, and the attacker has control over parts of the network, then plain-old DNS is not the only attack model. The attacker does not need to hack DNS, they can just manipulate the content on the wire.
EDIT:
Specifically: https://letsencrypt.org/docs/challenge-types/
It won't give you a wildcard certificate, but you don't need one for the type of attack we're talking about.