I posted a new debug token!
You can try disabling the DHCP option on the Macs and enter the desired IP, usually the one already setup at the router if you have DHCP reservations there, and also manually enter the DNS server there. This way, the Mac won’t try to assign itself a different IP/DNS servers when they lose connectivity. Sometimes they do, and when the PiHole comes back up, they don’t automatically switch to back to using PiHole or respecting router DHCP Settings. But, you also have to remember that this can also work against you. For instance, you’ll have to re-enable DHCP on the Mac if you lose connectivity when the PiHole goes down. Also, the router is pointing all DNS queries to the PiHole, so if the PiHole goes down, unless you have backup DNS servers, all devices will temporarily lose connectivity till you change DNS at the router or the PiHole comes back online.
still no success 
I would prefer not to tamper with the dhcp settings as you suggested.
any other ideas maybe?
I unfortunately still did not manage to fix this issue.
Please upload a fresh debug token. The older tokens have expired.
done in the first post!
Debug logs expire in 48 hours.
Yes I updated the first post with a new debug today.
i am still struggling. in case anyone has a tip I am super grateful!
debug is updated again!
thanks a lot!
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