In L2 pragmatics, only a few studies have examined task complexity. Furthermore, the existing studies have predominantly focused on the cognitive dimension and have lacked consistent findings. González-Lloret and Ortega (2018) and Pallotti (2019) have thereby contended that socio-interactional features be incorporated into task design. Along this line, this study investigated perceptions of L1 and L2 speakers of English regarding the difficulty of four role-play tasks with differentiated degrees of (dis)preference and imposition. Participants included 33 L1 speakers and 63 Korean L2 speakers at intermediate-level (n = 32) and high-level (n = 31). Results showed that participants’ perceived difficulty matched the design intentions exclusively affected by request size, responsibility for the problem, and persuasion across complex versions of the tasks. Moreover, the linguistic consequences of such factors entailed challenges among L2 speakers. There were also various factors that emerged for task difficulty other than the manipulated task design features, underscoring the importance of participants’ explanatory comments in L2 pragmatics.