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I would like to be able to access my ssh connections without having to type in the passphrase for my key file each time. Is that an app like Pageant that works with Cygwin to do this?

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Try ssh-agent:

DESCRIPTION
     ssh-agent is a program to hold private keys used for public key authentication (RSA, DSA).  The idea is that ssh-agent is started in the beginning of an X-session or a login ses‐
     sion, and all other windows or programs are started as clients to the ssh-agent program.  Through use of environment variables the agent can be located and automatically used for
     authentication when logging in to other machines using ssh(1).
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That works well. Thank you. I followed this guide mah.everybody.org/docs/ssh – firefusion Feb 1 at 15:33
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