Using a bastion host or jump server allows for easier security management as hosts that are not public-facing do not need to be secured as much as the public-facing host. If you need to SSH to the hosts within the private network, you will need to first SSH to the bastion host or jump server and SSH to the other host from there.
Having to connect through multiple hosts adds complexity on the client side. Some ways to help are setting up a VPN or proxy on the gateway and configuring the client connection accordingly.
If the gateway host is an SSH server, you can use the built-in ProxyJump option to automate logging in to reach the end destination through multiple hosts. This option, if paired with public key authentication method, could be a lifesaver for system administrators.
Related: How to SSH without password
user@host:~$ ssh user@gateway user@gateway's password: user@gateway:~$ ssh user@internal user@internal's password: user@internal:~$ exit logout Connection to internal closed. user@gateway:~$ exit logout Connection to gateway closed. user@host:~$
user@host:~$ ssh -J user@gateway user@internal user@gateway's password: user@internal's password: user@internal:~$ exit logout Connection to internal closed. user@host:~$
Use comma-separated value for jump hosts if multiple jump connection is required
$ ssh -J user@gateway,user@gateway2 user@internal
Add : to hostname / IP address to specify port if non-standard is used for SSH server.
$ ssh -J user@gateway:2222 user@internal
-J destination Connect to the target host by first making a ssh connection to the jump host described by destination and then establishing a TCP forwarding to the ultimate destination from there. Multiple jump hops may be specified separated by comma characters. This is a shortcut to specify a ProxyJump configuration directive. Note that configuration directives supplied on the command-line generally apply to the destination host and not any specified jump hosts. Use ~/.ssh/config to specify configuration for jump hosts.
Configure AllowAgentForwarding and AllowTcpForwarding to yes on the jump server if you're using SSH agent or public key authentication.
$ vi ~/.ssh/config
Host gateway hostname 192.168.111.27 user user
host internal hostname 192.168.111.38 user user proxyjump gateway
$ ssh internal firstname.lastname@example.org's password: email@example.com's password: user@internal:~$
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