There are several ways of doing this but none of them are good solutions. The way I would probably do it if I had to is like this:

1. Tunnel port 222 from your machine to port 22 server Y

   ssh -L222:localhost:22 servery

2. Create a dynamic tunnel from server X to server Y using the previously constructed tunnel. Note: your destination on this command is mymachine but the credentials you'll use are for server Y since it's what you're actually connecting to.

   ssh -D8080 -p 222 mymachine

3. Setup server X with a system wide SOCKS Proxy of localhost:8080

There are several ways of doing this but none of them are good solutions. The way I would probably do it if I had to is like this:

1. From your machine, tunnel port 222 from your machine to port 22 server Y

   ssh -L222:localhost:22 servery

2. From server X, create a dynamic tunnel from server X to server Y using the previously constructed tunnel. Note: your destination on this command is mymachine but the credentials you'll use are for server Y since it's what you're actually connecting to.

   ssh -D8080 -p 222 mymachine

3. Setup server X with a system wide SOCKS Proxy of localhost:8080

There are several ways of doing this but none of them are good solutions. The way I would probably do it if I had to is like this:

1. Tunnel port 222 from your machine to port 22 server Y

   ssh -L222:localhost:22 servery

2. Create a dynamic tunnel from server X to server Y using the previously constructed tunnel. Note: your destination on this command is for mymachine but the credentials you'll use are for server Y since it's what you're actually connecting to.

   ssh -D8080 -p 222 mymachine

3. Setup server X with a system wide SOCKS Proxy of localhost:8080

There are several ways of doing this but none of them are good solutions. The way I would probably do it if I had to is like this:

1. Tunnel port 222 from your machine to port 22 server Y

   ssh -L222:localhost:22 servery

2. Create a dynamic tunnel from server X to server Y using the previously constructed tunnel. Note: your destination on this command is mymachine but the credentials you'll use are for server Y since it's what you're actually connecting to.

   ssh -D8080 -p 222 mymachine

3. Setup server X with a system wide SOCKS Proxy of localhost:8080