Integral to some conceptualizations of the smart city is the adoption of web-based technology to support civic engagement and improve information systems for local government decision support. Yet there is little to no literature on the smartness of gathering information about historic places within municipal information systems. This chapter provides three case studies of technologically augmented planning processes that incorporated citizens as sensors of data about historic places. The first case study is of SurveyLA, a massive effort of the city of Los Angeles to comprehensively survey over 880,000 parcels for historic resources. A second case study involves Motor City Mapping, an effort to identify the condition of buildings in Detroit, Michigan and a parallel historical survey conducted by volunteers. In Austin, Texas, a university-based research team designed a municipal web tool called the Austin Historical Survey Wiki. This chapter offers insights into these prior efforts to augment planning processes with digitized memory, web-based technology, and public engagement.