Ok, as you know I'm interested in this one, smokie, so some long winded stuff here:
For me Pihole seems to work pretty well at suppressing unwanted stuff across all my devices.
The fefailt blocking (Gravity) list gets rid of a gazillion tons of stuff, but of course there are other multiple other lists available to add if you want. Google them up, paste the list url into the admin page in Pihole, done.
What I do is some tweaks. This is really just a case of using the query log the first time you go to a site.
Launch the query log in the Pihole admin web page for the device you are looking at (by clicking its name/ip in the dashboard)
Go the site of interest in a browser on that device.
Refresh the query log
Now you have a list of what the device is trying to do. Some sites will be whitelisted, some blacklisted, because they were on the Gravity list. Fiddle with them.
I usually start by blacklisting the lot other than the main site, then whitelist stuff a bit at a time until it works, but doesn't show ads. After a while you get to suss which are obvious trackers and ad servers.
It seems like a faff, and sometimes (like for all4) someone has done the work for you, so a google for the site name and "pihole" often yields exact things to block or not.
It seems like a faff of course, and it is a bit, but once it's done you don't have to do it again unless the web site changes drastically, and also you find that similar sites use similar tech. So I tweaked the bejeesums out of the Cambridge local news site to get rid of stuff, but now almost every local news site I look at is also sorted without me doing anything further.
As to My5, this was a mystery as I have it ad free, until I tried to replicate what you say. Turns out you're right - on a PC. I nerver watch on a PC so hadn't seen that behaviour. Site/player won't load, unless you allow the adobe asset tracker, it all works, but then the ads appear...
However, on my Fire Stick, My5 (and ITV Player and All4) all work with no ads at all, without any tweaking. I don't know why, so I'll leave that one.
I'm not sure whether Pihole 5 (I'm on 4) allows you to blacklist things on some sites and not others - so the adobe asset tracker might be allowed on My5 but nowhere else, or on one device and not another for example. I'll have to look into that one.
Lastly, it will never work on sites where they stream ads from the same domain as the main site (as Youtube does), so that's that. Use other solutions or live with it.
And my final bit of blether - I use it to stop trackers. So for example, as I don't use Facebook or have an account, all Facebook related stuff (just search the query log) I block. Loads and loads of sites try to talk to Facebook and send info - no more for me. Repeat as you want.
I have some games - in the background they want to send stuff back to the provider. I block them, my network is less loaded, they don't get to spy and the games still work. Makes me happier.
Microsoft - well, you can imagine, but loads can be blocked with Pihole at no detriment.
Google Analytics - none of that thank you.
etc etc. Depends how much you enjoy fiddling I guess.
I'm running at approximately 25% of all network traffic being blocked by Pihole (top of the admin page) and it all seems good to me.
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