A method and system for identifying and detecting improperly wrapped envelopes for use in a mailpiece fabrication system. The method/system visually images each envelope in predetermined regions of interest (ROIs) to determine the spatial relationship between the internal content material and one or more points of reference indicative of the internal bounds of a sealing adhesive. By examining the spatial relationship, a determination is made regarding the proximity of the internal content material and the sealing adhesive. If the distance, or spatial separation, therebetween is below a threshold value, then an assumption is made that the content material and sealing adhesive are contiguous and that the envelope has been improperly sealed, i.e., with the content material interposing or otherwise inhibiting the proper closure of the wrapped envelope.