[I log in with my chromebook and able to connect to internet.]
Actual Behaviour:
[Chromebook cannot connect to internet. When running the diagnostics on the chromebook, it says "DNS: No functioning DNS server available.]
Additional details:
I have many other devices that connect without issue. I am running on a raspberry pi 4 via this command: curl -sSL https://install.pi-hole.net | bash
On my router's configuration, I have it set to use my pi hole as the primary DNS on the DHCP Server settings.
On the chromebook, I have disabled "Use secure DNS". What is interesting is that when I look at the wifi settings on the network I am connected to, it is set to use "Automatic name servers" which point at my pi hole. If I switch it to "Google name servers", I can then connect to the internet but obviously isn't using my pi hole. Then, I can tell it to use "Automatic name servers" and I can connect to the internet and it is using my pi hole. However, every time I boot up, I have to go through this. Has anyone else seen this? Any suggestions/ideas? I apologize if this is already in the Help section - I did a search, but did not see anything that matched what I am seeing.
So basically you distribute Pi-hole's IP via DHCP and your Chromebook does report No functioning DNS server available after reboot if "Automatic name servers" is enabled. You you switch to "Google name servers" and then back to "Automatic name servers" it's working as expected?
Sounds like a bug in the Chromebook OS. Are you blocking DNS servers other than Pi-hole on your local lan?
Are there any queries after a reboot to the Pi-hole at all? I could image the Chromebook is doing some lookups which might be blocked by Pi-hole making the OS think there is no valid DNS resolution. Switching to google's servers does resolve the domains and afterwards the checked domains are not checked again making it work with Pi-hole as well.
I do not see any queries offhand. When I look at the chromebook, it says what it's IP address is. I don't see anything in the pi hole logs after I reboot the chromebook.
Some additional info: Chrome gives error DNS_PROBE_FINISHED_BAD_CONFIG. It allows me to run diagnostics. In the DNS diagnostics, it says "Attempting to resolve hostname: ccd-testing-v4.gstatic.com". Then it says "DNS server returned problem status code -137".
I tried adding "ccd-testing-v4.gstatic.com" to the whitelist, but that didn't seem to help. If it comes to it, I can live with the workaround of just switching DNS servers when I boot up.
So it failed to resolve ccd-testing-v4.gstatic.com. Try to use the long-term database and make sure that queries for that particular domain never made it to the Pi-hole. If this is the case, we can rule out Pi-hole as the point of failure.
Then it is something with your Chromebook not honoring the DNS settings.