Hi.
Usually the achievement triggers if you try again and get all 22 in the trunk at the same time.
Make sure you have all 22 cash bundles from the level in the trunk when you leave (punching-out back to the office). Just having 22 bundles, or 2 Million dollars worth of cash lying around in your office does not count. It has to all come at once, as the achievement description indicates.
Perhaps though it doesn't always work, which is a problem...
A few people have had the issue yes, though I'm not sure why. It works for everyone else.
The usual suspect is Steam itself, or Steam connectivity; it can drop out sometimes, or have trouble communicating the info. If that's the case, trying multiple times should have results.
Other than that, it's something we need to investigate further to fix.
It's on the list, but I can't say when we'll get to it.
