Test Windows Service Process

Suppose you are assigned to test a Windows service process. The process watches multiple directories (user configured, potentially across local files systems and network shares) for files to appear. As they appear, it notes the information in a database, makes a web service call, and moves the file to indicate that it has been processed. Considering all aspects of testing, give at least five examples of how you would test it (just a summary sentence for each example is sufficient).