A whiteboard cleaning system includes a user movement sensor that determines when a user is inactive; a whiteboard capture camera that makes an image of the whiteboard when the user movement sensor detects that the user is inactive; a classification module that classifies the image with a pre-trained image data set using an augmentation technique to enhance the size of the image data set and determines whether the whiteboard needs to be cleaned based on the classification, through transfer learning, using the image data set; and a wiper that cleans the whiteboard when the classification module determines that the whiteboard needs to be cleaned.