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source: Windows 10 Server (local port 8081)

destination: Ubuntu

ssh tunnel: Putty

Windows10 server------->ssh tunnel--------->Ubuntu

I have the ssh tunnel up between the source and destination

destination netstat:

tcp 0 0 192.168.1.106:ssh asdasd.asd.asd:62040 ESTABLISHED

source is binding on port 8081:

C:\Users\asd\Desktop>netstat -a | find /N "8081"
[29]  TCP    127.0.0.1:8081         asd_asd:0          LISTENING

Problem is, when I set the browser or system proxy to localhost:8081 on the source side nothing works. On the destination I ran a tcpdump matching against dest port 8081 to see if the packet comes out of the tunnel but looks like it doesn't:

asd@asdasd:/var/log$ sudo tcpdump dst port 8081
Password:
tcpdump: verbose output suppressed, use -v or -vv for full protocol decode
listening on eth0, link-type EN10MB (Ethernet), capture size 262144 bytes

I'm trying telnet on the source side to trigger the tcpdump:

C:\Users\asd\Desktop>telnet 127.0.0.1 8081

On the destination side I got the following enabled under sshd_config:

AllowAgentForwarding yes
AllowTcpForwarding yes
GatewayPorts yes

On the source side I have MS Defender off, checked the router logs nothing. It almost feels like the packets never get into the tunnel. Any idea how to troubleshoot futher?

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