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The game has no way to actually know if an addon is properly running in the latest update. It simply compares a number contained in the addon to a number contained in the game client. If they are not equal it will show the message and refuse to load the addon unless you check the allow outdated addons checkbox.
The number in the addon has to be changed manually by the author each time. Some forget to change it when they upload a new version, some simply won't do an update when the addon is still working and only the number would need to be changed.
The checkbox simply skips this check and loads the addon regardless, which offers the same result as changing the number in the txt file manually for each addon.
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