This isn't about light propagation delay; its a real causal sequencing failure. Read the Wikipedia article I linked upthread. It will make your brain hurt.
Relativity does amazing things. Here's a related example a physics prof of mine gave me. Imagine a man running with a 10-foot-long pole, held in the middle, aligned with his path of travel. He's running at a high fraction of c; high enough that the Lorentz factor is 2. So he sees everything in his path of travel squished by a factor of 2 along his axis of travel.
He's running toward a shed with an open door, that's 10 feet long in the rest frame. In the runner's frame, that means it's five feet long. So when he reaches it, the end of his pole reaches the back wall at the same moment he's in the doorway. His pole knocks out the back wall, and he's where it was as the back end of his pole reaches the doorway; the front end of the pole is now five feet past the former back wall of the shed.
Meanwhile, an observer in the frame of the shed is watching all this. He sees the runner and his pole Lorentz-contracted by a factor of 2, so it looks like the pole is only five feet long. So he sees the runner enter the shed, with the back end of the pole well inside the shed before the front end reaches the back wall.
Now, was the pole ever "really" entirely within the shed? There is no absolute answer. The runner says no, the shed-frame observer says yes, *and they're both right".