Non-alphanumeric characters in filenames and filepaths can lead to unintended consequences in digital preservation. The New Orleans Jazz & Heritage Foundation Archive conducted simple tests to investigate peculiarities related to this issue that surfaced when preserving their audiovisual assets. This case study resulted in a list of problematic, albeit commonly used, non-alphanumeric characters. It also uncovered significant implications for using proprietary cloud replication software as part of digital preservation workflows.