How to SSH Through Multiple Jump Hosts on Mac, iPhone, and iPad

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Connecting to a private server often requires routing through one or more bastion hosts, which can complicate credential and key management across hops. OpenSSH on Mac supports multi-hop connections via the -J flag or ProxyJump entries in the ~/.ssh/config file, allowing each host to have its own username, key, and port settings. Private keys stay on the local device and do not need to be copied onto bastion hosts, removing the need for agent forwarding. The same connection layout can be mapped to mobile SSH clients on iPhone and iPad, where organizing routes and credentials is especially important. Troubleshooting is recommended hop by hop using the -v flag to isolate whether failures are caused by reachability, authentication, or forwarding policy issues.

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