[SR-13591] REPL is not working on swift-5.3-RELEASE (Windows) · Issue #56026 · apple/swift · GitHub is a more thorough example, though some of the same bits are replicated at LLDB crashes when loading local variables - #2 by compnerd.
I imagine that there are a few more cases around on the forums and GitHub issues.
Although the REPL does work, it continuously regresses, and there is currently insufficient help to keep it in a great shape. It would be good to get more community support to keep the REPL in a working state at all times on Windows.