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Is there a way I can rig it so every machine I ssh into has already had 'set -o vi' run for my session, without having to change anything on machine I'm logging into?

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I think that's what RemoteCommand would do for you, as mentioned in the post, no?

I did try that but it just runs 'set -o vi' and exits. He shows using it to launch a multiplexer... I suppose it's an alternative to 'ssh -c command'. I tried to figure out a way to invoke 'set' followed by the remote user's $SHELL but couldn't figure it out. I'll keep fiddling; thanks for your reply

From the bash man page:

All of the single-character shell options documented in the description of the set builtin command, including -o, can be used as options when the shell is invoked.

So set RemoteCommand to something like /bin/bash -o vi

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