Systems and methods for automated detection of changes in extent of structures using imagery are disclosed, including a non-transitory computer readable medium storing computer executable code that when executed by a processor cause the processor to: align, with an image classifier model, a structure shape of a structure at a first instance of time to pixels within an aerial image depicting the structure captured at a second instance of time; assess a degree of alignment between the structure shape and the pixels, so as to classify similarities between the structure depicted within the pixels and the structure shape using a machine learning model to generate an alignment confidence score; and determine an existence of a change in the structure based upon the alignment confidence score indicating a level of confidence below a predetermined threshold level of confidence that the structure shape and the pixels within the aerial image are aligned.