I didn't realize someone had replied to this I recently gave Sync another try and Helen's assessment regarding the media scanner was correct. I'm using Sync 1.4.50.0 on Android right now and the Autoupdate Gallery advanced option looks like it's intended to do what I've asked for here. I don't know if it's working for deleted files though. I just loaded up my camera, took a picture, let it sync, deleted it on my PC, let it sync, and re-opened my camera app on Android. I swear it didn't work last night before I deleted most of my pictures, but today it did (with only 2 pics on the camera). The deleted picture gets removed from the library without a reboot, but the timing leads me to believe the camera app is causing the refresh needed, not Sync. The refresh didn't seem to occur until the camera app was loaded. However, my observation could also be the result of the changes being reflected lazily (ex: deleted or changed files are flagged dirty in the media database and aren't refreshed until an app request them). Keep in mind, there's a lot of assumptions on my part there. I'm using Android 4.4 and I know the API related to media scanning was changed and might impact the way deletions are handled. A few links I happened across while searching for how it works... http://android.stackexchange.com/questions/57913/how-do-i-refresh-rescan-the-sd-memory-in-android-4-4-kitkat http://stackoverflow.com/questions/15147536/how-to-trigger-mediascan-on-nexus-7 http://stackoverflow.com/questions/8379690/androids-media-scanner-how-do-i-remove-files I don't need another reply. I just wanted to clarify what I was asking for.