This is something I've experienced as well, at least 3 separate times with FedEx. Every single time the estimate changes to an earlier date, the package ends up arriving later than the original date.
The Friday before the Monday which they were scheduled to deliver, I got a delivery exception saying that it was unable to be delivered according to my instructions and that nobody was home. I WAS home, though I was not notified they were coming, and I can't think of a scenario which "inside or outside the gate" does not cover.
On Monday, Tuesday, Wednesday, and Thursday they updated to say it was 'out for delivery', each time updating in the evening to say the following day after they failed to return to my house. It was finally delivered 1 hour after I left for the airport.