"How do I use paramiko to SSH to a remote host while proxying through a jump host? Also, my jump host requires two-factor authentication!"

This seems to be a surprisingly common problem with a lot of not-very-working solutions. I figured I'd share my attempt with the world.

A simple class, SSHJumpClient, which derives from paramiko.SSHClient and implements two additional features:

1. Easy chaining of SSH connections, supported through object injection. This enables the programmer to build a 'stack' of proxied SSH sessions, and tunnel commands through infrastructure as-needed.
2. Easy authentication scheme override, forcing a keyboard-interactive authentication approach to be used. This should support most 2FA / MFA infrastructure approaches to SSH authentication. The keyboard-interactive authentication handler is injected, permitting easy integration with more advanced use cases.

In this example, we use keyboard-interactive authentication on the Jump Host, and we tell Paramiko to 'auto add' (and accept) unknown Host Keys. (What could possibly go wrong?)

import paramiko
from paramiko_jump import SSHJumpClient, simple_auth_handler

# My Jump Host requires keyboard-interactive multi-factor
# authentication, so I use auth_handler=. Otherwise, I could
# use paramiko.SSHClient here.
with SSHJumpClient(auth_handler=simple_auth_handler) as jumper:
    jumper.set_missing_host_key_policy(paramiko.AutoAddPolicy())
    jumper.connect(
        hostname='jump-host',
        username='jump-user',
    )

    # Now I instantiate a session for the Jump Host <-> Target
    # Host connection, and inject the jump_session to use for
    # proxying.
    target = SSHJumpClient(jump_session=jumper)
    target.set_missing_host_key_policy(paramiko.AutoAddPolicy())
    target.connect(
        hostname='target-host',
        username='target-user',
        password='target-password',
        look_for_keys=False,
        allow_agent=False,
    )
    _, stdout, _ = target.exec_command('sh ip int br')
    print(stdout.read().decode())
    target.close()

from getpass import getpass

import paramiko
from paramiko_jump import SSHJumpClient, simple_auth_handler

with SSHJumpClient(auth_handler=simple_auth_handler) as jumper:
    jumper.connect(
        hostname='jump-host',
        username='jump-user',
    )

    target1 = SSHJumpClient(jump_session=jumper)
    target1.connect(
        hostname='target-host1',
        username='username',
        password='password',
        look_for_keys=False,
        allow_agent=False,
    )
    _, stdout, _ = target1.exec_command('sh ver')
    print(stdout.read().decode())
    target1.close()

    target2 = SSHJumpClient(jump_session=jumper)
    target2.connect(
        hostname='target-host2',
        username='username',
        password='password',
        look_for_keys=False,
        allow_agent=False,
    )
    _, stdout, _ = target2.exec_command('sh ip int br')
    print(stdout.read().decode())
    target2.close()

circuit = []

hop1 = SSHJumpClient()
hop1.connect('host')
circuit.append(hop1)

hop2 = SSHJumpClient(jump_session=hop1)
hop2.connect('host')
circuit.append(hop2)

hop3 = SSHJumpClient(jump_session=hop2)
hop3.connect('host')
circuit.append(hop3)

hop4 = SSHJumpClient(jump_session=hop3)
hop4.connect('host')
circuit.append(hop4)

target = SSHJumpClient(jump_session=hop4)
target.connect('host')
circuit.append(target)

target.exec_command('uptime')

for session in reversed(circuit):
    session.close()

In order to successfully authenticate with infrastructure requiring keyboard-interactive multi-factor authentication, you will probably want to explicitly pass in auth_handler= during client construction. A basic handler callable is included, and should work for most use cases:

from paramiko_jump import simple_auth_handler

When troubleshooting authentication failures, remember that Paramiko will be authenticating as a client on each 'hop', and that it has strong preferences over which authentication scheme it will be using. You can control authentication behavior by passing various parameters to the `connect()` call. Read `paramiko.SSHClient._auth` for more insight into how this works.