What is the sample rate of the existing file/song when this occurs?
Is it 24/48, 16/48, 16/44. or?
Sounds like it may be a mismatch in the system somewhere, like the file is 16/44 and you're trying to force ASIO to 16/48 or something similar
Also make sure the Windows bitrate matches the ASIO and the file; that one can hide and cause issues ..
Windows will sometimes assign a different audio driver if the ASIO device isn't turned on first (before RB is opened) here, which can get confusing.