The pivotal role of communication in second language (L2) learning has triggered plethoric research to identify factors that may influence learners’ willingness to communicate (L2 WTC). However, there is a dearth of comparative research on L2 WTC, especially among EFL learners studying English at different educational institutions. To this end, the present study investigates the role of ‘grit’ and ‘classroom enjoyment’ (CE) in learners’ L2 WTC in two different educational settings of public schools and private language institutes. Grit includes two lower-order constructs, namely perseverance of effort (POE) and consistency of interest (COI), which were examined separately in this study. A total of 269 Iranian students from both public schools and private institutes completed an online survey. What was revealed from the data analysis through the Mann–Whitney u-test, Spearman’s rho, and multiple regression analysis is that private institute learners enjoyed higher levels of WTC compared to public school students. While POE and CE exerted a significant effect on L2 WTC in both educational settings, COI failed to do so. The findings of this study are discussed from a socio-educational perspective with regard to the difference between these two educational contexts.