I am attempting to create what should be a rather simple function, isInTrash, to return whether a file path passed to it points to a location in any trash. This thread https://developer.apple.com/forums/thread/110864 got me partway there, but the results I am getting don't match with what I expect. Function: func isInTrash(file: String) -> Bool { guard let fileURL = URL(string: file) else { return false } var relationship: FileManager.URLRelationship = .same let defaultManager: FileManager = FileManager.default do { try defaultManager.getRelationship(&relationship, of: FileManager.SearchPathDirectory.trashDirectory, in: FileManager.SearchPathDomainMask(rawValue: 0), toItemAt: fileURL) } catch { NSLog("Unable to get relationship of path to trash.:\n") } return relationship == .contains } Unit Test: func testInTrashPaths() { XCTAssertTrue(handler.isInTrash(file: "/Users/username/Trash/foo")) //fails XCTAssertTrue(handler.isInTrash(file: "/Users/username/.Trash/foo")) //fails XCTAssertTrue(handler.isInTrash(file: "/Users/username/.Trash/bar")) //fails XCTAssertTrue(handler.isInTrash(file: "/Users/username/.Trash/blah")) //fails XCTAssertTrue(handler.isInTrash(file: "/Users/username/.Trash/test/bang")) //fails XCTAssertFalse(handler.isInTrash(file: "/Users/username/Desktop/test/bang")) //succeeds } The tests that should return true all fail. The negative test succeeds, but that's not really a surprise. If I switch to testing for .same instead of .contains, then the first Assert succeeds ("/Users/username/Trash/foo"). Two questions about that behavior. it appears that while the actual path, if you open the trash in a terminal and use pwd, is /.Trash, the api treats it as /Trash. Why? /Trash/foo returns .same instead of .contains. Why is it saying that a file inside the trash has a relationship of .same to the Trash? It's very clearly a contains relationship. What's going on? If I sanitize the inputs by substituting "/" for "/." using replacingOccurrences(of:with:), then everything except the negative test fails. When I step through in the debugger, I find that now a path to a file on the desktop is returning .same for the Trash! WHAT!?!?!? WHY!?!? I would dearly love to know what I'm doing wrong here.