VS Code jump-box setup with SSH keys - ssh

Question

Establishing an SSH connection via a jump box
Hi everyone, I have been trying to set up my environment on VS Code to run my code from my Windows laptop on a remote Linux server (through my University department's proxy), by following this tutorial. It is working fine, but every time I connect to the host, I need to enter my password and would like to avoid this by configuring my SSH keys - it seems like I haven't found the proper way to do so.
Generating the keys
Let's call my local Windows machine local, the proxy host1 and the final endpoint host2. I created a private/public key pair on local, transferred the public key to host1 so that it is now in ~/.ssh/authorized_keys, and repeated the process by generating a new key pair on host1 and transferring the public key on host2. I followed the instructions here for generating and transferring the keys:
Generate key on local:
ssh-keygen -t rsa -b 4096
Transfer public key to host1:
$USER_AT_HOST="your-user-name-on-host#hostname"
$PUBKEYPATH="$HOME\.ssh\id_rsa.pub"
$pubKey=(Get-Content "$PUBKEYPATH" | Out-String); ssh "$USER_AT_HOST" "mkdir -p ~/.ssh && chmod 700 ~/.ssh && echo '${pubKey}' >> ~/.ssh/authorized_keys && chmod 600 ~/.ssh/authorized_keys"
Generate key on host1:
ssh-keygen -t rsa -b 4096
Transfer public key to host2:
export USER_AT_HOST="your-user-name-on-host#hostname"
export PUBKEYPATH="$HOME/.ssh/id_rsa.pub"
ssh-copy-id -i "$PUBKEYPATH" "$USER_AT_HOST"
VS Code config
I then edited my config file according to this, which now looks as follows:
Host host1
HostName host1
User me
ForwardX11 yes
IdentityFile C:\Users\Me\.ssh\id_rsa
Host host2
HostName host2
ProxyCommand C:\Windows\System32\OpenSSH\ssh.exe -q -W %h:%p host1
ForwardX11Trusted yes
User me
IdentityFile ~/.ssh/id_rsa
It seems that the first jump works fine (I don't need to enter my password twice) but I am still asked for it when establishing the connection. My guess is that I haven't configured the IdentityFile properly? When connecting through PowerShell in two steps (i.e. SSH into host1 and then host2), I don't need to enter my password. I would really appreciate any advice!

Answer 1

I've been stucking in the same situation.I tried a lot ,and finally managed to connect without password prompts. Below it's how I've done it, Hope it'll help.
Suppose I(machine A) want to connect to machine C via Machine B(JumpServer), generate keys using ssh-keygen on machine A, then copy the content of public key file(default as id_rsa.pub) to authorized keys file(default as authorized_keys in .ssh folder) of both machine B and machine C(or using ssh-copy-id if available). At last the IdentityFile field of both hosts of machine B and machine C in the config file(host1 and host2 in your case), fill them with ~/.ssh/id_rsa or C:\Users\your_user_name.ssh\id_rsa(the private key you generate on machine A ).
Finally it connects as expected.(I guess in this siutation but not for sure that the identity file in the local machine A is always the subject to connect, so machine B and machine C need to use the identity of machine A for all authorizations)

Answer 2

I met exactly the same situation, that is making this ssh connection: local (Windows) -> host1 (Linux) -> host2 (Linux)
The problem here is that for the second jump to host2, the ProxyCommand "ssh.exe -q -W %h:%p host1" actually looks for host2's IdentityFile "~/.ssh/id_rsa" on local. Because the keys you generated on host1 is different from the one on local, using the key on local would fail to make the second jump.
Solutions:
Simply use the same key for two jumps. Copy the id_rsa.pub on local to host2's authorized_keys.
Copy the key files on host1 to local, rename them and fill host2's IdentityFile with the path of the key file on local.
Referring to this question, modifying the ProxyCommand may enable ssh to use the key on host1 during the second jump. However, I haven't been able to make it work on my Windows local machine.