Trust dilemmas arise whenever individuals perceive opportunities to benefit from engaging in trusting behaviour with others, yet recognize that doing so entails the risk of exploitation. My research examines the determinants of judgement and choice within such dilemmas. To do so, I adopt a multi-method approach that includes the use of both laboratory experiments and qualitative field research. The aim of this multi-method approach is to enhance the ecological validity of trust knowledge by investigating both social psychological and organizational processes that influence trust judgements and decisions. The benefits of trust have been amply established in many empirical studies, ranging from laboratory/experimental investigations (Ostrom and Walker, 2003) to field studies in social and organizational settings (Sztompka, 1999). Obtaining the full range of benefits from trust, however, is often problematic in practice (Cook, Levi and Hardin, 2009; Hardin, 2002; Kramer and Cook, 2004). One problem is that the anticipated gains from trust materialize only when social actors happen to be dealing with others (that is, someone willing to reciprocate their own trusting behaviour). Misplaced trust – engaging in trusting behaviour with individuals who exploit that trust – can be enormously costly. Accordingly, it makes sense for individuals to trust, but only when that trust is likely to be reciprocated by others.