This is just a hack, but hopefully this helps someone else. As others have mentioned in this thread, while the tutorial sets the serve command as: tailscale serve -bg https://127.0.0.1:11000, what worked for me was using tailscale serve -bg --https=443 http://127.0.0.1:11000. This ensured that the Nextcloud container properly spun up and was reachable using https://server.my-tailnet.ts.net. However, Nextcloud Office was still not loading, with logs from the collabora container indicating that it couldn't reach my Tailscale domain. I edited the /etc/hosts file on the collabora container with a reference to the domain and the Tailscale IP address (usually 100.x.x.x): docker exec -u root nextcloud-aio-collabora sh -c "echo '100.x.x.x server.my-tailnet.ts.net' >> /etc/hosts" Validate that this worked using: docker exec -it nextcloud-aio-collabora cat /etc/hosts, and you should see an entry with the tailnet URL. After this, I was able to create/edit files. I added this command as a user script to run whenever the array starts as well.