I'm having problems with proxychains on WSL2

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Reference HTB academy module: Dynamic Port Forwarding with SSH and SOCKS Tunneling (https://academy.hackthebox.com/module/158/section/1426)

Hey there, I'm having a problem where I'm not able to reach the 172.16.5.19 host in an internal network through a pivot host.

Here is my setup:

  1. I'm using Kali Linux on WSL2 (because convinience)
  2. I have setup a dynamic port on 9050 like in the module. ssh -D 9050 ubuntu@<target_ip>
  3. Now that I have done this, I also have the following in my proxychains.conf:
tail -4 /etc/proxychains.conf

dynamic_chain
proxy_dns
socks4 127.0.0.1 9050
  1. now when I try and use proxychains (nmap, msf, curl literally anything) gives me a !!!need more proxies!!! error or just doesnt route through the tunnel.

So to test with a basic setup I tried using proxychains with TOR as follows:

  1. Setup tor with config file as follows:
tail -2 /etc/tor/torrc

SocksPort 9050
SocksListenAddress 127.0.0.1
  1. Now restart tor service sudo service tor restart
  2. With the same proxychains.conf file as above I try and run:
proxychains curl https://check.torproject.org

ProxyChains-3.1 (http://proxychains.sf.net)
|DNS-request| check.torproject.org
!!!need more proxies!!!
!!!need more proxies!!!
!!!need more proxies!!!
|DNS-response|: check.torproject.org does not exist
curl: (6) Could not resolve host: check.torproject.org

Any help would be appreciated. I'm assuming the problem is im using kali on WSL2 but that really shouldn't matter from a networking POV. Feel free to DM me or reach out at discord Elus1nist#9042

Thanks in advance!

Apparently proxychains works flawlessly on the HTB provided pwnbox (native parrotOS I guess). So it is a WSL2 thing which I would love to fix. Any Help accepted.

I have provided details of what I have tried in my question above. Tunneling over VPN and basic tor setup both not working with proxychains.

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