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I asked this question in stackoverflow and it was suggested to try here so here goes...

I'm planning on provisioning a web server and database server in a server farm environment. They will be in the same network but not in the same domain, both windows server 2008 and the database server is sql server 2008. My question being, what is the best way to secure data in transport between the servers? I've looked into IPSEC and SSL but not sure how to go about implementing either.

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Most popular DBMSes have native SSL support usually easily enabled through configuration:

Most DB access APIs and libraries also provide functions for opening a secure connection using SSL:

That would probably be the easiest and most direct route. Now, if you have other network services that you also need to tunnel through a secure connection, then OpenVPN would probably be the better choice.

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You can create a vpn (OpenVPN) between you servers, maybe the configuration will be a little more complex if both your servers are on same subnet.

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Wouldn't ipsec be much easier if they're on the same network? Not sure how it handles cross-domain connectivity in Windows since I'm a Linux person. – kaerast Jun 17 '10 at 8:50

Try to read and watch this How-to-Encrypt-Telnet-Traffic-with-Windows-Firewall-with-Advanced-Security-and-IPsec, I didn't watch entire video. but maybe is what you are looking for!

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