>UPDATE: Spoke too soon…
The problem discussed here turned out to be specific to Little Snitch 6.1 and not a general issue in macOS. It will be fixed in an update of Little Snitch later today.
New title from source: Warning: DNS encryption in Little Snitch 6.1 may occasionally fail
> @dang is a no-op. The only way to get reliable message delivery is to email hn@ycombinator.com
> Warning: DNS encryption in Little Snitch 6.1 may occasionally fail