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But if the game is monitoring it, why can't it remember that I deserve it so that I get it when the connection re-establishes?
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Because when you perform Action X, the game reports to Steam that you have earned Acheivement X. Unless the game was specifically designed to handle the case when there is no internet connection, it wouldn't keep an internal list of the acheivements; it would just report to Steam and assume that everything went fine.
I don't get your question; if the Steam application were monitoring the games, then it almost definately would remember that you earned the acheivement.