I can’t think of any problems I’ve faced in over 3 years. I have an app on my phone that I can use to temporarily disable my Pi-hole if I need to do some testing, but I don’t know if I’ve ever had a situation where the Pi-hole was the source of a problem. Definitely not a maintenance headache. I run an update on it every now and then, but only because I see a notification that there is one, not because there’s something going wrong.

My gf likes to click on ad entries of Google searches - that doesn’t work

You have full control over what you block and whitelist. So if anything goes wrong, you can just troubleshoot it and whitelist if needed. If all fails, you can always (temporarily) turn off all blocking in pihole.

DNS blocking is heavily dependent on the blocklist(s) you use. It’s entirely possible to block >95% of crapware, and break companies’ ability to track you without compromising usability.

Having used both for a lot of years, I’d say look instead at AdGuard Home. It is also FOSS but supports more out of the box; including certificate management, the ability to use encrypted DNS both upstream and downstream without need for third party software (cloudflared), the ability to use adblock filter syntax (lists are 200k lines instead of 2 million lines, but actually block more), and so on. PiHole has some improvements pending in the next version, but it’s not there yet in comparison, imho.

I’d also strongly suggest you check out Hagezi’s DNS blocklists, as they’re pretty much set and forget. They’re intended to be used as your only block list, and do an excellent job (see testing in the Discussions on their GitHub). Use the Normal list if you don’t want to deal with false positives occasionally, and the Pro++ list if you don’t mind getting your hands dirty (whitelisting occasionally) and want to block every last scrap of annoyance and anti-privacy crapware on the web. Both will significantly improve your online experience.

Depending on how you configure it you can run into issues with sites and apps that use trackers.

Nope, no issues.

Quite often, yes, especially for apps.

For nearly a year the Android Amazon app wouldn’t work. It would load, and then when a tracker failed to start, would show a generic error message page.

US bank mobile app wouldn’t login for about 2 months last year.

This happens quite often when apps are built with dependencies they assume will load, and when there is a failure an error boundary catches it and shows an error view.

My most frequent issue is that links created through an email service provider like ConvertKit will get blocked by PiHole.

I’m a small business owner and so I get a lot of other people’s newsletters, on purpose. I like seeing what mentors and colleagues are doing with their businesses. But a link to their website, a blog post, anything really will almost always be blocked by PiHole if it’s sent via an ESP. This kind of “tracking” (email clicks from a small biz I know and trust) is something I am totally fine with.

It’s easy to disable for 1 minute to click through, but sometimes I forget that the PiHole is active and I can’t figure out why the links aren’t working.

Yes, but first go check which list you want to use since they’re a good starting point to understand a kind of level of tolerance and expectations around your experience.

There’s lots of lists around here’s a small sample:
https://arstech.net/pi-hole-blocking-lists-2023/

Be prepared for a bump in time outs as you work through things you might need (I blocked by accident a bunch of needed Microsoft services that I need to use during my job).

I haven’t edited my white list in months, maybe over a year. It’s going very well. I’ve been running pihole on ubuntu for more than 5 years as two virtual machines. I’m happy.

Depends on what lists you add to pihole (or adguard).

The default lists for both are primarily advert or tracking related, and very safe to keep. The only time I whitelist is when I’m following some kind of shopping deal that uses a tracker. Most linux related things are free from that.

Most things just work, and I have 3.5 million domains blocked. When something doesn’t work you can go into the query log to see what was blocked, and whitelist it from there. I seldom have to do this. Some apps are written to fail completely if they can’t send their telemetry, but most just work without the ads.

Been running it 7 years with a combined adlist of 1,089,320 domains.

It’s really rare that I run into a site that won’t load or function correctly (like once maybe twice a year). The most noticeable really is the ad results in Google, but I’ve moved away from that to DuckDuckGo anyway.

In the few cases that you do want to use a blocked doman; you can open pihole and either whitelist the domain with one click right out the query log, or disable pihole blocking entirely for 5sec-30min with one or two clicks.

If you really want to, you can group clients and adlists so some clients have much stricter blocking than others do. You can even leave some devices completely free of blocking while still using pihole to log their traffic.

By far one of the noisiest blocked domains is Nvidias driver telemetry. If you don’t strip it out using NVSlimmer, it’ll constantly retry its phone home, spamming the pihole with dns requests (not enough that it can’t handle, but enough that it’s VERY noticeable in the dashboard)

Been using pi-hole since 2016 and I’ve had to make but a handful of exceptions over he years. I guess it’s a case by case thing.

There might be a chance for false-positives. Or to just clog your dns responses with repetitive queries.

Then again, you don’t need more than a HaGeZi blocklist anyway.

Only if you like watching commercials on paramount +