Failure dns name resolution and unrecognized service dnsmasq

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Expected Behaviour:

dns resolution should be happening from raspberry pi command line. It's not.
-operating system
Raspbian 11 bullseye
-hardware]_
Raspberry pi 3

Actual Behaviour:

error message failure in dns name resolution. Network is setup as Location A: raspberry pihole within tailscale environment. Locate B: ubuntu computer also within tailscale environment. They can communicate with each other. Cannot ping fully qualified domain names from within pihole raspberry pi.
Everything was working for weeks and then when I tried to update/upgrade getting failure in name resolution.

Debug Token:

I can't upload the token because inside raspberry pi unable to do name resolution to get to your support area. I do have a copy of it though. Should I post it here?

This will temporarily reset the nameserver on the Pi to bypass Pi-Hole DNS.

sudo nano /etc/resolv.conf

Edit the nameserver line to nameserver 9.9.9.9 or your preferred third party DNS service, save and exit

Run

pihole -d

and upload the debug log.

Thanks!

https://tricorder.pi-hole.net/iqClvo4h/

Any luck with the debug log?

Uploaded the requested file. No response. Should I close this request and try other sources? Still looking for a solution.

We are all volunteers here, and frequently get busy with other activities in our lives. Upload a new log and post the token URL. Your old one has expired.

Thanks. No pressure just asking. Here is a link to the log. Very much appreciate the help offeredy by the volunteers. I know everyone has activities and am not pressuring.

https://tricorder.pi-hole.net/s6GvBSBT/

Your debug log is normal. Your Pi-hole appears to be working normally.

*** [ DIAGNOSING ]: Name resolution (IPv4) using a random blocked domain and a known ad-serving domain
[✓] a407.casalemedia.com is 0.0.0.0 on lo (127.0.0.1)
[✓] a407.casalemedia.com is 0.0.0.0 on eth0 (192.168.1.92)
[✓] a407.casalemedia.com is 0.0.0.0 on tailscale0 (100.80.184.80)
[✓] doubleclick.com is 142.251.40.206 via a remote, public DNS server (8.8.8.8)

"unrecognized service dnsmasq"

This part of your post title was not addressed in your comments. What are the specifics of this part of your problem?

That is the message I would receive on the command line when ssh'ing into the raspberry pi running pihole and try to ping a fully qualified domains name. It would work if, for example, I tried to ping the ip address but not the domain name.

Perhaps this is related to another issue with the pihole. In Ubuntu network manager I've always input the ip address of the pihole as the DNS under the IPv4 tab. I find that if I input the local pi address of the pihole, i.e., 192.168.8.12, for example, then upon startup I can only ping ip address, not fully qualified domain names. I then input 192.168.8.12, 9.9.9.9, in that same field and things then work. However, I don't think that's the way it should be.

As well, the /etc/resolv.conf keeps re-setting to a pihole on a remote internal network in tailscale. Even though I've input into Network Manager to use the local pi-hole, upon ubuntu startup the local computer resets to the remote pihole within a tailscale environment. This happened after an Ubuntu update/upgrade yesterday.

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