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I noticed on my first record playback that the replay just stopped at what seemed to be a random spot, so I kept an eye out in my next game. It seems like the recording automatically stops either when you save the game or start up a saved game. Anyone else run into this? Was playing skirmish, only big things I recall altering were pop limits to like 3000.

The playback recording only starts on start of the game. It does not activate after loading a game save, but saving the game should not interrupt it.
It's because playback files are constructed to simulate the whole game step-by-step, and starting recording with units / buildings already present could cause synchronization problems.
I believe this feature was developed mostly for multiplayer users, so it allows them to detect cheaters or improve their gameplay by analyzing mistakes. Multiplayer games are very rarely loaded from the game save, so it doesn't look like a big problem.