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The small business that I work at uses FileMaker as its heart and soul. We finally got a copy of FileMaker Server 11, and now our database is hosted on a proper server, rather than on the secretary's computer.

My boss wants to be able to work on the remotely-hosted FileMaker database from home. There is an IP address and port on our local network that I could forward through our router then configure with DynDNS, but I don't want to do that, because it would present a huge security risk. I've been trying to set up a VPN for the last few days, but I still can't get it to work with our network, and I'm considering trying a completely different approach.

Is there any way that I could set up an SSH tunnel from my boss's laptop to FileMaker Server's port, but without leaving the forwarded port sitting there open for anyone to access? Despite a lot of Googling, I've not found one word of anyone accessing a remotely-hosted FileMaker database from outside the local network and having any sort of security on the port.

I'm still extremely inexperienced as a sysadmin (if I could even be called that), so I apologize if this is a completely ridiculous question - but my job description is "guy that gets paid to figure all of this out because nobody else at the office can", so that's what I'm doing here now.

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you could do that, but for usability's sake I recommend OpenVPN on your gateway host, and Tunnelblick on the connecting Mac(s). That is relatively painless to setup, there are tons of how-tos, and Tunnelblick offers a nice client for the user that "just turns on" VPN if they want.

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Thank you so much - I'll look into this in the morning. For the record, though, only one computer in this equation is a Mac - our database is hosted on a Mac Mini Server, and my boss's laptop is running Windows 7; will OpenVPN GUI and Tunnelblick play nicely together? –  kivetros Mar 29 '11 at 1:06
    
Tunnelblick is the Mac OS OpenVPN software. It, and the Windows OpenVPN software, play nicely with OpenVPN on my Linux gateway. –  Florenz Kley Mar 31 '11 at 9:48
    
oh, and feel free to ask about OpenVPN... it's pretty easy. –  Florenz Kley Mar 31 '11 at 19:26
    
I will, when I get back to that... he pulled me off that project a few days ago and started me on something else. (Oh, the joys of working at a small business.) –  kivetros Apr 1 '11 at 11:45

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