In recent decades, U.S. cities have invested in rail transit for reasons beyond supplying alternatives to driving. Increasingly, rail investments are specifically promoted to reshape the built environment for property-led economic development. In these cases, new investment in rail transit is claimed to facilitate particular types of land use changes, mostly in the form of dense multi-family residential and mixed-use developments. Although rail’s effects on land use are widely claimed, scholarly evaluations offer mixed results. This paper examines two potential reasons for these mixed results. First, as most empirical examinations tend to be conducted shortly after new transit investment opens analysis is often criticized on the basis that short time frames may not allow land use changes to materialize. The second is that rail investment often includes changes to local zoning and land use regulations, creating opportunities for types of development that were previously outlawed. This paper evaluates these two critiques through an analysis of long-term land use effects associated with new rail transit service in San Diego, California. The results suggest that even after three decades of development cycles, rail transit has not led to consistent regulatory patterns of increased density or new mixed-use development.