Here’s another one, not sure if it’s in the database or not.
It’s just a little NE of my house.
I first noticed this when looking at the aircraft located at N 23 30 01.15, W 97 16 43.40 (you can copy and paste this into Google Earth). I noticed that it looked too large compared to the house next to it, so I measured it, then compared it to another MD-80 parked at DFW airport. This plane in flight measures 250 feet long, about double its true length. The camera that took the photo is about twice as high as the airplane in flight, way too low for a satellite.
Isn’t this effect less pronounced the closer the shadow-casting object gets to the Earth? It is quite noticable of the moon’s shadow (moon’s shadow, moon’s shadow 
) during a solar eclipse, for example, but I think the effect is negligible for airplanes. At that distance (about 6-7 miles at cruising altitude for a commercial passenger jet) the sun is effectively a point source at infinite distance and the shadow is the same size as the airplane.
The effect is larger than you think. Check David Simmons’ second post.
You can see the effect yourself on your own shadow on a sunny day. Your ankles’ shadows are fairly sharp, but your head’s shadow is noticeably less so.
On the ground, you’re 6-7 miles farther away from the sun than the plane, yet you can clearly see the sun is not a point source.