DHCP issue - sometimes

Done multiple times in the past. In fact each time it used to happen I would reboot the pi - soft reboot but it has been powered down, unplugged and turned back on since as has the router and the devices that have issues.

Any other thoughts on this? If I get a chance I may start the setup from scratch (wipe SD card and start from there) but seems like a nuclear option to fix (if it does) when this only started after updating to pihole 4.2

Your ipv6 setup might be incorrect on the bridge interface.
I dont have enough experience with ipv6 to know what to look for (maybe someone else can?).

If start fresh, try setup with ipv4 only.
And without a bridge at first.
If get this working, add the bridge configuration.
If that works, configure/add ipv6.

Also the dnsmasq-dhcp part is not maintained by Pi-hole (Pi-hole is forked from dnsmasq).
Could post your issue below:

http://lists.thekelleys.org.uk/mailman/listinfo/dnsmasq-discuss

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