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No, no, no, don't put the bolt in from the outside. Like Chip said, you won't be able to turn the nut because it will be inside the recess. Also, if you lose the nut in there, it will be even harder to retrieve than the bolt.
As I recall (I just did this a month ago) you have to carefully thread the short extension and the socket into the recess to pick up the bolt, which if you had heeded my earlier advice to not pull completely out of the car (like Chip said), should just make it to the other side. It took my wife and I both to line both the upper control arm and the bolt.
It's definitely possible to do it with the engine in the car, although it may be tight.
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