Figuring out what dirmngr is doing in these cases, can be aided with
cranking up verbosity and logging the output, e.g.:

keyserver hkp://ipv6.pool.sks-keyservers.net
log-file /tmp/tmp.pVKaTIdXs8/.gnupg/dirmngr.log
debug-level guru

Options in $GNUPGHOME/dirmngr.conf. Followed by gpgconf --kill dirmngr.

Whilst plenty of stuff is logged.... it doesn't actually tell me if he
hit things over ipv6 or ipv4. It appears to be resolving a pool and
picking a random thing to connect to.

Note the https://bugs.gnupg.org/gnupg/issue1989

dirmngr supposed to figure out that something is dead, is retry
elsewhere. Does using hkp://ipv6.pool.sks-keyservers.net improve things
for you? That pool should have all servers accessible over ipv6, unlike
the main pool which may have ipv4-only servers.

Could you please crank up the logging, and check if it has excessive
amount of resolving dns pools and messages marking them dead?

** Bug watch added: bugs.gnupg.org/gnupg/ #1989
   http://bugs.gnupg.org/gnupg/issue1989

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https://bugs.launchpad.net/bugs/1625845

Title:
  dirmngr doesn't handle IPv6 properly

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