> Can you help me figure out why this bug doesn't show up in the normal Python REPL?

That's because the normal Python REPL works very differently when in interactive mode. This is because the tokenizer in interactive mode is coupled with reading from standard input. 

We would need to somehow decouple this behaviour with interactive mode, allow a new option to the parser that allows activating this mode and then hook this to codeop module (and maybe other places).