/.well-known/acme-challenge/<challenge> does not make it to the web server; /.well-known/<challenge> does - has anyone seen this before?

Yeah, I agree with Rudy and Peter this is most likely a Palo Alto Networks firewall causing a problem. We have seen several different symptoms from their recent (last few months) changes to their default rules.

The first set of symptoms is shown here:

Later variations of this are to see a response but with a certain set of response headers for requests to your server. But, that is not your case. Another variation is to only happen when using a user-agent that matches the Let's Encrypt servers. Your tests show this is not your variation.

In short, you are suffering from the "Classic" Palo Alto block :slight_smile: (almost certainly)

Look for an Application Rule about "acme protocol" in your firewall.

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