Originally Posted by bfrye
Best I can say is to update the status and if it says "Upgrade Required" or "Install Required", then it should upload it. If it says "Up to Date", and the software is installed on the handheld, then you're good.
Don't misinterpret this because it is in jest
That's very NOT true as much as your statement makes sense. All the status really does is tell you if it has installed the software, just because it knows it needs to does not mean it will right now. I had some apps I was testing that I just gave up on and went to bed only to find they finally showed up sometime, randomly, no rhyme or reason.
So, if this is something anyone is going to test be sure not to get your hopes up that you'll know if you did it right instantly.