Mac: Unable to connect to pihole

Caprischoso · February 26, 2025, 10:22pm

Please follow the below template, it will help us to help you!

If you are Experiencing issues with a Pi-hole install that has non-standard elements (e.g you are using `nginx` instead of `lighttpd`, or there is some other aspect of your install that is customised) - please use the Community Help category.

Expected Behaviour:

MacOS Studio 15.3.1

Expected to see pihole gui interface

Installed The official Pi-hole Docker image from pi-hole.net via docker desktop 4.37.1. For ports set 70,71,72,73.

Actual Behaviour:

when connect to ipaddress:70
Safari: "the server unexpectedly dropped the connection"
Chrome: "this page isn't working ... err empty response"
Firefox: "The connection to the server was reset while the page was loading."

Fing shows that the ports are in use
70 gopher
71 netrjs-1 Remote Job Service

Debug Token:

(https://tricorder.pi-hole.net/GokXTqza/)

rdwebdesign · February 27, 2025, 12:48am

Please upload a debug log and post just the token URL that is generated after the log is uploaded by running the following command from the Pi-hole host terminal:

docker exec -it <pihole-container-name-or-id> pihole -d

where you substitute <pihole-container-name-or-id> as required.

Also, include the compose file or docker run command used to start the container.

Caprischoso · February 27, 2025, 2:17am

Didn't I already upload the log? The debug token in the original post did not work?

Got an error after running your command and saying yes to upload:

** The debug log can be uploaded to tricorder.pi-hole.net for sharing with developers only.*

[?] Would you like to upload the log? [y/N] y

- Using curl for transmission.*
- curl failed, contact Pi-hole support for assistance.*
- Error message: curl: (22) The requested URL returned error: 400*

[✗] There was an error uploading your debug log.

- Please try again or contact the Pi-hole team for assistance.*
- A local copy of the debug log can be found at: /var/log/pihole/pihole_debug.log*

What's next:

Try Docker Debug for seamless, persistent debugging tools in any container or image → docker debug pihole*
Learn more at docker debug | Docker Docs*

Don't know how to upload to tricorder.pi-hole.net. Went to that webpage and it was blank.

Also, include the compose file or docker run command used to start the container.

I guess that is a YML file? Have no idea how to find it.

This is from the "copy docker run" in the containers section:

docker run --hostname=59fb53649f45 --env=PATH=/usr/local/sbin:/usr/local/bin:/usr/sbin:/usr/bin:/sbin:/bin --env=DNSMASQ_USER=pihole --env=FTL_CMD=no-daemon --network=bridge --workdir=/ -p 70:443 -p 71:53 -p 72:53/udp -p 73:67/udp --restart=no --label='org.opencontainers.image.created=2025-02-24T18:11:26.797Z' --label='org.opencontainers.image.description=Pi-hole in a docker container' --label='org.opencontainers.image.licenses=NOASSERTION' --label='org.opencontainers.image.revision=29b604af3f1e65523dbb0971749efed236e151fa' --label='org.opencontainers.image.source=https://github.com/pi-hole/docker-pi-hole' --label='org.opencontainers.image.title=docker-pi-hole' --label='org.opencontainers.image.url=https://github.com/pi-hole/docker-pi-hole' --label='org.opencontainers.image.version=2025.02.6' --runtime=runc -d pihole/pihole:latest

Caprischoso · March 1, 2025, 7:08am

Spent a bit of time looking at similar posts. Some of the diagnostic things they mentioned:

strong text/ # sudo pihole-FTL --config webserver.port
80o,443os,[::]:80o,[::]:443os

/ # nslookup pihole
Server: 192.168.65.7
Address: 192.168.65.7#53

My network is 10.0.0.x so have no idea what this is referencing

Does Pihole running under docter run its own webserver?

Bucking_Horn · March 1, 2025, 8:40am

Remapping ports 53 and 67 won't work, even less so if you do map them differently for UDP and TCP:
Clients will send their DNS requests to port 53, the standard port for DNS.
Also, they would broadcast for a DHCP server on port 67, the standard port for DHCP, but even with port 67, broadcasts would not reach your container, as Docker isolates that in a separate link when using bridge network modes (and anyway, you would only need port 67 if you intend to enable Pi-hole as DHCP server).

Caprischoso · March 1, 2025, 10:44pm

Thanks for the detailed explanation. So I put "0" for the 4 port values when setting it up. Now I get:

/ # sudo pihole-FTL --config webserver.port
80o,443os,[::]:80o,[::]:443os

/ # nslookup pihole
Server: 192.168.65.7
Address: 192.168.65.7#53

But where is the server?
sudo lsof -i -n -P | grep TCP doesn't show any of these ports being in use

docker exec -it pihole pihole -d

lists a bunch of IP addresses none of which are my normal local network 10.0.0.x:

**** [ DIAGNOSING ]: Network routing table*

default via 172.17.0.1 dev eth0 *
172.17.0.0/16 dev eth0 scope link src 172.17.0.2 *
**** [ DIAGNOSING ]: Networking*
[i] Default IPv4 gateway(s):
```
172.17.0.1%eth0*
```
- Pinging first gateway 172.17.0.1...*
- *** [ DIAGNOSING ]: Name resolution (IPv4) using a random blocked domain and a known ad-serving domain*

[✓] www.booking.extranemt-heosting.com is NOERROR on lo (127.0.0.1)

[✓] www.booking.extranemt-heosting.com is NOERROR on eth0 (172.17.0.2)

[✓] doubleclick.com is 142.250.189.174 via a remote, public DNS server (8.8.8.8)

**** [ DIAGNOSING ]: Discovering active DHCP servers (takes 6 seconds)*

Scanning all your interfaces for DHCP servers and IPv6 routers*
Timeout: 6 seconds*
Error while sending Router Solicitation on eth0: Network unreachable*
No answer on eth0*

hostsdir=/etc/pihole/hosts
no-resolv
port=53
server=8.8.8.8
server=8.8.4.4

-rw-rw---- 1 pihole pihole 53K Mar 1 22:09 /etc/pihole/pihole.toml
[dns]
upstreams = [
"8.8.8.8",
"8.8.4.4"

*** [ DIAGNOSING ]: contents of /etc

-rw-r--r-- 1 root root 222 Mar 1 22:09 /etc/resolv.conf
nameserver 192.168.65.7

So there are 7 IP addresses listed. What address do I use to access the pihole? With pihole installed in Container Station on my QNAP NAS I access it at http://10.0.0.70/admin/.

Caprischoso · March 1, 2025, 10:50pm

The Docker list of pihole ports makes it even more confusing:

Bucking_Horn · March 1, 2025, 11:11pm

You can't remap 53 and 67 to 0 either.

You have to publish and expose the same ports, e.g. 53:53/udp.

Caprischoso · March 2, 2025, 4:52am

Thanks for your quick response. Tried

errored out

but pihole is my only container

Caprischoso · March 2, 2025, 4:57am

and in macos terminal

sudo lsof -i -n -P | grep TCP

doesn't show that the port is in use.

Caprischoso · March 2, 2025, 11:17pm

Tried again this morning and the error went away and pihole started

/ #  sudo pihole-FTL --config webserver.port
80o,443os,[::]:80o,[::]:443os

 # nslookup pihole
Server:         192.168.65.7
Address:        192.168.65.7#53

** server can't find pihole: NXDOMAIN

unable to generate debug log:

/ # docker exec -it pihole  pihole -d
/bin/sh: docker: not found

Log file shows:

2025-03-02 14:48:25 2025-03-02 22:48:22.754 UTC [191M] INFO: Web server ports:
2025-03-02 14:48:25 2025-03-02 22:48:22.754 UTC [191M] INFO:   - 0.0.0.0:80 (HTTP, IPv4, optional)
2025-03-02 14:48:25 2025-03-02 22:48:22.754 UTC [191M] INFO:   - 0.0.0.0:443 (HTTPS, IPv4, optional)
2025-03-02 14:48:25 2025-03-02 22:48:22.754 UTC [191M] INFO:   - [::]:80 (HTTP, IPv6, optional)
2025-03-02 14:48:25 2025-03-02 22:48:22.754 UTC [191M] INFO:   - [::]:443 (HTTPS, IPv6, optional)

sudo lsof -i -n -P | grep TCP

doesn't show that the ports are in use

trying to connect to localhost:;80 "safari can't connect to the server localhost"
trying to connect to http://127.0.0.1:80 " can't connect www.127.0.0.1:80 because the page's address is invalid

Caprischoso · March 3, 2025, 5:16am

netstat | grep 53
kctl 0 0 53 3 com.apple.net.netagent
kctl 0 0 53 7 com.apple.netsrc

Bucking_Horn · March 4, 2025, 1:56pm

That's the expected result, unless you'd have explicitly named your Pi-hole host pihole. pi.hole (note the dot) is the default name as provided by Pi-hole.

The machine that ran that command cannot find the docker executable.
Was that run from the machine hosting your Docker installation?

system · March 25, 2025, 1:57pm

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