Ran that without any issues, but the the status of dnsmasq is still failed. Here's my debug token: du4vq3gstt
What did that command output (the dnsmasq one)?
Nothing, it went right to the prompt.
For clarification, does that mean it does not output anything but runs (may appear as it would hang) or does it mean that it exited immediately without printing anything?
If you want to use a port below 1024 this forces you to run all network daemons with superuser privileges, which might open security holes. Hence, this security model is obsolete IMHO and today it only gives a false sense of security and contributes to security holes.
TL;DR You have to run dnsmasq as root.
Sorry for a late reply, the command exited immediately without any output.
Okay, so your dnsmasq is immediately exiting without printing an error. This is very weird but maybe you can find a similar issue using e.g. Google?
Maybe the binary got damaged, you could try
sudo apt-get install --reinstall dnsmasq
Just wanted to update you guys on this. I ended up installing Raspbian Stretch on my RPi & the installed pihole. It's working fine now.
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You inadvertently stumbled on to the solution by installing stretch, since the fix is in dnsmasq 2.76.
The actual problem is detailed below, along with a fix for jessie.
The solution I first discovered here:
https://www.raspberrypi.org/forums/viewtopic.php?t=128449#p919942
Then found the bug ticket here:
https://bugs.debian.org/cgi-bin/bugreport.cgi?bug=860064
The diff patch to fix is here:
https://bugs.debian.org/cgi-bin/bugreport.cgi?att=3;bug=858506;filename=dnsmasq-init.patch;msg=27
You can install a more recent version of DNSMASQ here:
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