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, an outline of a structure at a first instance of time to pixels within an image depicting the structure captured at a second instance of time; assess a degree of alignment between the outline and the pixels depicting the structure, so as to classify similarities between the structure depicted within the pixels of the image and the outline 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 outline and the pixels within the image are aligned.