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What is the best way to implement automated updates? I've gotten as far as libcurl, I imagine I need to ping the server every now and again with the current version of the software. But then what should I do? What server tech needs to respond, and how?

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I'd have the server run a checksum on itself and then respond with that checksum. If the checksum is current, then the system continues on as normal. Otherwise, you'd push the update to the server and undertake the steps necessary to install it. Using diff is also an option.

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