Thank you Quinn, this fixed it for those paths that lead to extant files. It does seem that JWWalker is also correct that the file must actually exist within the trash. This is unfortunate, as I'm trying to filter rename events based on having a destination in the trash. If this API call only returns .contains when there is actually a file at that location, then it won't work for files that aren't there yet. I'll have to figure out something less elegant it appears.