This paper presents system design challenges and issues with sensing through walls at different standoff distances and wall types. Efforts for developing sense through the wall (STTW) systems, such as those undertaken by the US Army Technology Objective (ATO) program, aim at providing the soldier with situational awareness information before breaching a building in a military operations in urban terrain (MOUT) environment. STTW capabilities also support law enforcement and search and rescue applications. Since 2002, extensive evaluations of STTW technologies, most notably those performed by the Communications Electronics, Research, Development and Engineering Center (CERDEC) Intelligence and Information Warfare Directorate (I2WD), have been made to determine which technology could be the most viable solution. After conducting comprehensive studies, I2WD initiated several Phase I efforts and Phase II efforts. The purpose behind both efforts was to develop various STTW technology demonstrators under a 5 year ATO. Many lessons learned during the development of Phase I systems were incorporated into the considerations for Phase II developments. This paper discusses design challenges and issues with sensing through walls at different standoff distances and wall types through lessons learned and results from modeling and simulations performed by the Army Research Laboratory.