The highly lethal attacks against land transportation targets in Madrid and London have sparked considerable amount of debate in Singapore about the terrorist threat to the local land transportation infrastructure. How real is this threat and what can be done to counter it? This is the central question addressed in this paper. While transportation targets in general have always been a terrorist favorite, in recent years there has been an increased emphasis on attacking soft transportation targets such as mass transit. There are several distinct reasons for this development, including the increasing difficulty of successfully striking other targets, the ease of producing large number of casualties, the panic-spreading universality of the city bus or metro car, economic impact on the afflicted state by crippling workforce mobility and deterring foreign investment and tourism, symbolic value, and an overall high probability of success and a low level of risk. Indeed, since 1991 more than 42 percent of terrorist strikes worldwide were directed specifically against land transportation, producing the highest casualty rates of any type of terrorist attack. With regards to the threat to Singapore’s transit system, analysis of Jemaah Islamiya’s ideology and targeting patterns reveals an increasing preference for soft, Western, mass-casualty targets in Southeast Asia. But while Singapore’s commuter transportation system fully encompasses all of these adjectives, the recently weakened Jemaah Islamiya currently possesses only very limited capability to strike this type of target with significant results. Still, other adjacent threats exist including a possible attack by a home-grown terror cell, attempted suicides by deranged individuals, or the disruption of service via a wave of hoaxes by pranksters or terrorist group sympathizers. Despite the relatively low level of threat, Singapore has made many preparations and preventive measures that other countries that have experienced surface transportation terrorism have identified as pillars of effective public transportation security. These essentially include prevention, effective response and timely mitigation, and psychological defence measures.