Hi Jason, clip names should overwrite no matter the date. It shouldn't matter importing via Watch Folder or not. Make sure your Tria Express or Tria+ is updated to latest version, software downloads are free on rossvideo.com, but important note if your Tria is older and not on Windows 10, it needs to be updated, and it is a specific Windows 10 Enterprise version so you would need, so contact Tech Support if you need assistance.
#Tria