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Why does ssh on mac cause a socket error?

jp flag

I am trying to connect to a server - lets call it destination_server on port 22. I only can access the destination_server via a ssh-tunnel. The ssh-tunnel should use another server - proxy_server on port 81 - to then connect to the destination_server. I tried everything, really everything, the internet threw at me but I still always get stuck connecting. Currently I use the following command to first enable the ssh-tunnel connection:

 ssh -N -L 8080:127.0.0.1:81 proxy_username@proxy_server 

The last lines of the verbose output are:

debug3: ssh_connect_direct: entering
debug1: Connecting to proxy_server [proxy_server] port 81.
debug3: set_sock_tos: set socket 3 IP_TOS 0x48

I tried to fix this by enabling the SOCKS-Proxy with 127.0.0.1:8080 in the system settings:

enter image description here

But I still get the above mentioned debug message.

I also tried third party applications like SSH Tunnel Manager but there I can't add a password for the proxy. Then I bought JellyfiSSH from the App Store. This has a dedicated field for the tunnel connection but somehow it has to field for the private key for the destination_server.

I really can't seem to find a solution since no one on the internet seems to have the same debug output as me. I do always get the output regardless of the server I am trying to connect to. That's why I really would appreciate any help! Thank you all in advance!

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