I think the issue here is that the Steam program installed on your computer doesn't cache acheivement reports.
You're expecting too much of developers who have no online content in their games to have to handle every eventuality. You're certainly expecting too much of Valve if you think that the Steam platform should be able to monitor the memory state of every single game. Have you any idea how difficult that would be and, as a result, how much bigger and more complicated the program would need to be? Do we need another discussion about elegance in software solutions?
But, like I said, I am surprised that the Steam program doesn't keep track of acheivements even when its offline.
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