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I recently re-discovered autossh. I’ve been using it to persist mounted sshfs volumes but am only just now realizing it’s the scratch for some of my other itches.
With it I can
autossh -M50000 -t -D1080 -Nf crashingdaily.com
to keep a seemingly persistent SOCKS proxy running.
Or
autossh -M50000 -t crashingdaily.com 'screen -aAdR autossh'
to maintain an interactive session.
The value that I missed earlier is that the connections are maintained (re-established, actually) even if I change networks – which my laptop and I often do.
Jon’s View has a nice posting on using autossh for SOCKS proxying.
And Dread Pirate PJ has a good instruction for combining autossh and screen for persistent interactive sessions.
autossh is available for OS X via Darwin Ports and Fink and for Linux as source code or as binary packages from repositories for most modern Linux distributions.