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I have developer a server/client application that could see 100's of clients installed. Each client might only be accessible over the internet.

When I update my server application it's likely the clients will need updated too. What's the easiest (for the end user of my server/client application) to upgrade their server and all their clients at once?

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from the sounds of it your application may be slighly better then a virus. – tony roth Jan 31 at 0:54
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Build the functionality into the client application. Have it check periodically and/or on startup a web url for a manifest file that you host, and if a newer version is available, download it and replace the files. This will most likely require launching a separate updater executable.

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