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

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.