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I did something: I succeeded in implementing scenario 3 (approximately). This happened like 30 minutes ago therefore I'm not 100% sure that all I'm writing is solid.

I replaced tinyproxy with privoxy and configured sock5 connections to be forwarded from privoxy to tor sock5 port with this privoxy config line

forward-socks5t / 127.0.0.1:9050 .

Exactly as it's described in the manual.

So, recapping:
* my pc is connected to streisand via vpn (UDP) * streisand runs tor configured as relay and bridge * tor browser is configured to connect to my streisand privoxy proxy and then to reach my streisand tor bridge

Some post-work analysis and reflections on results

IT'S BLOODY FAST !!! SUPER FAST !!! DID I MENTION IT'S FAST? The speed is compatible to the regular browsing speed. Apparently, it just takes longer when resolving domains but then it flies!

Now, that's too fast . Suspiciously fast!

• I checked the tor circuit. All good.
• I checked each link contained in this page picked randomly. All the pages are clean from ads. I still have to figure out how to make privoxy log the stripped content but it's obviously removing ads

Do you smell something wrong?

I'm quite concerned about the dns queries. Where are they happening? At proxy level or at tor (exit) level? Can I use my own dns to resolve private domains and leave all the other domains to the tor circuit?

Any help would be appreciated. Thanks.

> Charles Proxy for iOS lets you capture and inspect network requests and responses on your iOS device. You can view metadata, headers and bodies in the app, so you can finally debug your app’s networking issues without a computer.

There's also a desktop app: https://www.charlesproxy.com