[chasil]

If you don't have an agent running with an accessible key, then you will get three password prompts, with suggestions for any default keys.

The final target is a pre-elliptic curve OpenSSH server, so legacy is enabled. I could probably have removed that for clarity.

  C:\Users\me\>ssh -J me@bhost1,me@bhost2 -o KexAlgorithms=diffie-hellman-group14-sha1 -o HostKeyAlgorithms=ssh-rsa -o MACs=hmac-sha1 oracle@target
  Enter passphrase for key 'C:\Users\me/.ssh/id_ed25519':
  me@host1's password:
  Enter passphrase for key 'C:\Users\me/.ssh/id_ed25519':
  me@host2's password:
  oracle@target's password:
  Last login: Wed Jun 24 13:29:55 2026 from bhost2

That client is Microsoft's port of OpenSSH.