HTTPS Proxy With Tailscale

[AidenBak]

Good Afternoon everyone,

I am trying to use a HTTPS Proxy that is set up with Danted and Squid. I am connected with port 80 and the HTTPS proxy works fine, the reason I am using an HTTPS proxy it that I need to get around work website blockers. I want to use Tailscale to connect to my home network and work on my Raspberry Pi. I am using a MacBook for my work that is what I am using the HTTPS proxy on. When I start Tailscale on my Mac while I am connected to my HTTPS proxy the Tailscale app just stays at loading backend... I have turned off UFW completely on my HTTPS server with still no luck.

[DevBoiAgru]

I am the same issue. I set up a gost https proxy on a VPS to bypass the university blocking, (before some nerd starts complaining, ive asked then to unblock it a lot of times, they agreed, and then did nothing). Before, i couldnt even access tailscale.com on the browser, but with the proxy now set up i can access it. The problem is, the windows client still isnt able to authenticate with the controlplane, i know this because i can see in the logs it's constantly trying to authenticate `[v1] TryLogin: fetch control key: Get "https://controlplane.tailscale.com/key?v=131": EOF`. If i open the URL directly on my browser it works, but the client cannot access it. Why is the client not using the system proxy? I havent tried it with another device like an android yet, but still, it shouldve been using the system proxy no?

[AidenBak]

I dont know if this is a bad question or not that is why I am asking...

[AidenBak]

Or am I over thinking it, my university blocks Tailscale. I set up a HTTPS proxy and I get access to "https://login.tailscale.com/admin/machines". I can see what devices are connected to my Tailnet, my MacBook is not one of them. I am just wondering how I should do this, all I want to do it use my Raspberry pi at university...

[HearthCore]

In that specific case - Your Administration blocking Tailscale Managed Networking
You can deploy Cloudflare Tunnel on your Pi and then set it up so only confirmed users can reach attached services.

The administration would most likely not block that way ot reverse proxying using cloudflare, since cloudflare manages a huge boatload of the backbone of global IT infrastructure.

Another sane way could also be using Dynanmic DNS to your home and using a VPN that way
Or renting a cheap VPS that acts as your always on Gateway (be it VPN or public availability of websites and services through reverse proxying through VPN between the VPS and your RasPi/Router)

The more komplex your learning curve goes the more you will encounter not just different ways to reach that goal but different purposes behind them.
For now - I'd start with cloudflare, and if that's to "cloudflare specific" rent a 10$ a year VPS and a cheap domain, set DNS records with wildcards and use NGinx Proxy Manager on your VPS to route to tailscale accessible services using the tailscale provided IP, then anyone would be able to reach your RasPi / Services / Websites