If you have a firewall enabled on your Pi open port 443 if you get timeouts, it might help

[MrD]

Hey Alexandros,

we have discussed the issue of changing IPv6 prefixes extensively in this forum. Have a look whether you can enable ULA addresses in your network.

More information is available in this FAQ article:

Use IPv6 ULA addresses for Pi-hole

Many users have reported that frequently changing IPv6 addresses cause page load to be slow or even prevent from working at all. The issues can be fixed by updating the IPv6 address in /etc/pihole/setupVars.conf followed by a run of pihole -g. However, this solution turns out to be very inconvenient since it might be necessary to change the IPv6 address on a regular basis (maybe even multiple times a day). An alternative approach we are currently looking into is the usage of ULA addresses which…