I'm having some trouble getting pi-hole working on RPi Zero W

This is confusing, and I’m sorry for that. Let me try to explain again.
-I have a Windows system and a Ubuntu system in my network.
-I bought a Raspberry Pi Zero and installed pi-hole on top of Raspbian Lite (no desktop, no browser).
-Ad blocking did not work on my Windows nor my Ubuntu systems.
-Recently, I received a new Raspberry Pi (Pi 4 8GB, hence the confusion when I say Raspberry Pi). Sorry about that.
-Upon testing, as before ad blocking does not work on Windows nor Ubuntu. Ad blocking does work on the new Raspberry Pi 4 when I use the Chromium browser, and I believe I have disabled ad blocking in the browser.

So, it seems weird that I have ad blocking working on the Raspberry Pi 4 when it isn’t working on my 2 other systems.

Oh, and setting up the new RPi 4, I had networking issues for a while. I set the static IP and networking wasn’t working for a while because I either hit the wrong number (1 instead of 0, seems unlikely) or Raspbian changed the IP for some reason. It’s working now and I don’t have any idea if something like that caused ad blocking to work. Seems weird.

What do your windows and Ubuntu machines connect to for internet access?

I’m not sure how to answer. I’m connecting wirelessly; do you mean what type of router?

Sorry, I see the answer to that question in the first post.

This just tells the router where to start automatically assigning addresses. Any manually assigned address can be outside that range.

Back on topic…
The pi hole serves the request for an ad with some other address than the ad server. Do we know what that address is? (Probably

Also, in the screen shot of your routers DNS settings the (optional) label makes me wonder if it defaults to some address if there is nothing in the DNS box.

Anyways, if you ping a blacklisted address from the pi it gets a reply from localhost. This is the pi as it is known to itself. This means the request for ads from a site is being replied with the internal IP of the pi. This is good, the pi is not an ad server so you won’t get any ads and the site is satisfied that it received a response and won’t keep asking.

The other thing to try is a traceroute this will show you the hops a packet takes to a given website. Traceroute a blacklisted and a non-blacklisted site and see if the packets are passing through the pi at all.

What if you blacklist the address of your windows machine and try pinging it from your Ubuntu machine?

I think the router is bypassing the pi because it’s just routing packets to your modem because it knows the YouTube IP address doesn’t reside on it’s local network. The modem then handles the DNS situation. Add the Pi’s address as the DNS on your modem and see what happens.

1 Like