Welcome to the Let's Encrypt Community
I'm going to ask for some help with this one.
I know in the past that these "HTTPSConnectionPool(host='acme-v02.api.letsencrypt.org', port=443): Max retries exceeded with url: /directory
" errors have frequently been associated with IP address blocks. Sometimes they go unsolved or seem to mysteriously resolve themselves without explanation or followup.
Here's a recent, very similar case:
Does the staff have any thoughts here?