Idiot User - Troubles After Updating Raspberry Pi OS

Everything was working fine until I tried to update my PiHole recently. I got the prompt that my Raspberry Pi OS was no longer supported (I think I was on Debian 9). I used the command given to ignore the OS check, and after it ran, it's saying the FTL service can't be reached, or something like that. I also can no longer reach the web portal.

So here's what I'm thinking; I'll just update to the latest Pi OS and reinstall PiHole. My question is basically how?

Ideally, I'd like to keep my settings and custom black/white lists if possible. I didn't do a ton of customization really, just specified the DNS servers I'd like to use mostly. Is there a folder or something I can just copy off my SD card and put in the new installation? Is there an easier way?

Any/all help is appreciated.

Debian 9 is no longer supported by either Pi-hole or Debian. In fact, Debian 9 produces a hard fail in Pi-hole.

Use the teleporter function of Pi-hole (web admin GUI > settings > teleporter). Save your teleporter file to to some location on a computer (other than the Pi), then import the saved settings from the GUI after you flash a fresh OS and reinstall Pi-hole.

Appreciate the help! Unfortunately, I can no longer access the web admin GUI. I know, I know, I should have run the teleporter before attempting to update. I'm an idiot. Is there another way I can run it?

pihole -a -t will do it, but the file is saved in the open directory on the Pi. You will need to copy that file to a remote location (i.e. off the Pi) so it will be available after format and re-flash.

Shoot. It's giving me this message:

tail: cannot open '/var/log/pihole/pihole.log' for reading: No such file or directory
tail: no files remaining

Am I totally boned?

What is the exact command you typed?

I specified pihole -a -t

Did you type pihole -t instead?

 pihole -a --h
Usage: pihole -a [options]
Example: pihole -a -p password
Set options for the Admin Console

  -p, password                    Set Admin Console password
  -c, celsius                     Set Celsius as preferred temperature unit
  -f, fahrenheit                  Set Fahrenheit as preferred temperature unit
  -k, kelvin                      Set Kelvin as preferred temperature unit
  -h, --help                      Show this help dialog
  -i, interface                   Specify dnsmasq's interface listening behavior
  -l, privacylevel                Set privacy level (0 = lowest, 3 = highest)
  -t, teleporter                  Backup configuration as an archive
  -t, teleporter myname.tar.gz    Backup configuration to archive with name myname.tar.gz as specified
      -t, tail [arg]
           View the live output of the Pi-hole log

             [arg]             Optional argument to filter the log for
                               (regular expressions are supported)

I typed exactly...

pihole -a -t

...then hit enter. When I did so, it just gave me...

pi@pi-hole:~ $

...again without any confirmation or anything. I took that to mean nothing happened, but does that mean it ran successfully?

Since I assumed nothing happened, I then did...

pihole -a
pihole -t

...which gave me the "cannot open" message I posted previously.

Apologies for the stupid picture-of-a-screen reference. My physical setup is wonky.

Now run the following command from that same directory and it will show the .tar.gz file with the teleporter backup. That is the file you want to save external to the Pi.

ls -lha

Aha! I think I see it! Thanks so much for all of your help! This really saved my butt!

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On a related note here's a handy way to get that teleporter file out to safety. In the directory where the file is located run the command

python3 -m http.server 8888

This runs python's mini built-in web server on port 8888 (you can use any port as long as it's not in use by something else).

On your main computer fire up your browser and go to your Pi-hole's IP address and use that same port number


You'll see a list of the files from the directory and in there you'll see the teleporter file. Right-click it and save to your computer.

Quit the python server with Ctrl-C.

It's a handy quick way to transfer files on your home network.

1 Like

THIS! ^^^

This last comment is gold, and definitely provides an easy method for those who aren't comfortable or familiar with other more traditional ways of moving files from a Linux-based system to another volume in the network.

Maybe sticky this, or include it somewhere in the docs? Just a suggestion.

Thanks, @chrislph!

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