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I am looking for something like autossh, but for windows. I have had trouble setting up autossh with cygwin. I am tring MyEnTunnel now, but I was wondering if Windows hacks know of something better.

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Is there particular reason it needs to be a SSH tunnel rather than a more general VPN? (i.e. you don't control the host and/or its firewall so can't install a VPN solution)

If not then perhaps using OpenVPN or similar would be more reliable for you - it deals with connection drops such that the streams operating through the link don't even notice.

If the problem is SSHd dropping your connection due to inactivity, try ensure both client and server have keep-alive packets enabled, and if that is not possible (or doesn't resolve the issue) have the SSH session that is running the tunnel regularly echo something back to the client (a loop of "output date with date then sleep some seconds"). Though neither of these keep-alive solutions have any effect if your problem is due to a network issue like a complete connection drop.

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I use Bitvise Tunnelier daily for a tunnel for synergy from my laptop to my desktop. It restarts fairly reliably when moving from network to network.

Here's an example shortcut target I use in my startup folder:

"C:\Program Files\Bitvise Tunnelier\Tunnelier.exe" -profile="C:\Users\username\My Documents\synergy-tunnel.tlp" -connectOnStartup -menu=small -exitOnDisconnect

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