A grace time is accorded to deletion events before initiating any server-side deletion. In many programs (like Microsoft Word), deletion is often just a save: 1. Save data to temporary file ~wrdxxxx.tmp 2. Delete Example.doc 3. Rename ~wrdxxxx.tmp to Example.doc See https://support.microsoft.com/en-us/kb/211632 So, upon deletion, wait a bit for any save operation to hopefully finalize, then sync. This is not 100% foolproof, as saving can last for more than the grace time, but probably the best we can do without mind-reading third-party programs.