this post was submitted on 18 Sep 2025
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I wonder how much longer that will work. DNS over HTTPS is now a thing and totally defeats the mechanism of a pihole.
VPN running on a WRT router? I know very little about this stuff I just know the buzzwords for street cred.
Pihole's act as a DNS or "Dynamic Name Server". All internet traffic is IP based once it leaves your home because routers dont know how to forward traffic for "https://samsung-ad-hell.com/", so there is a dedicated kind of packet for "Where is https://samsung-ad-hell.com/ located?" and that is a DNS Lookup. The Pihole pretends to know because it maintains a list of bad urls that host websites that only support privacy exploitation and advertisements and tells them "oh you want to go to 0.0.0.0, that's where you'll find your stuff" as it snickers.
But DNS Lookups were always plain text. When your laptop says "Where is https://big-booties.com/" your ISP knows you want porn. Now there is a new variant called "Secure DNS Lookup" which encrypts the url you're asking about. The ISP knows you're asking for a domain's IP, but it can't know which one and it no longer cares. Neat.
The trouble is that the Pi-Hole can no longer protect us from all the stupid fucking smart devices that want to earn a fraction of a penny per device by spying on us because THEY use the new Secure DNS Lookup.
Interesting... Well, this prompted me to search what Pi-Hole has done for this, and they seem to have a way to continue blocking even DoH, using "cloudfared", which is another daemon that needs to run with Pi-Hole... They can't possibly think their enshittification will continue to work.
It works on 99% of consumers. As long as preventing the enshittification from stealing your data requires effort and knowledge, this will continue to be the case. Hence the arms race between enshittifiers and human beings, two grouos that are mutually exclusive.
Me yelling "enhance" at my router so it blocks ads better
I can tell you didn’t read the manual because it obviously states that you have to be staring over the top of sunglasses for that configuration option to work.
Maybe block the DoH endpoint and in theory the device might fall back to normal DNS, dunno if that would work.
and also block outgoing connections to port 53 when it's not the pihole device's allowed IP
DoH is tricky to block since it's just using https on port 443. The only options are blocklists of known servers and attempting to detect it with deep packet inspection.
Yeah gotta inspect the traffic and block whatever hostnames it uses.
I'm speculating, but it wouldn't change a thing. You would still need to request domain addresses from a server somewhere, but traffic between your device and server would be encrypted in transit. The DNS server would also be verifiable to prevent imitators.
So, the request would go to the PiHole and if it was not being filtered the PiHole would make the request of whatever upstream server is configured same as before.
the difference is that it's very hard to block doh connections because it looks like web/API traffic. and if you don't block it, it will work around your pihole without you noticing. pihole only works if your devices actually use it without evading it, or if you can firce them to do so. doh is not used for connecting to pihole, it does not even support it.