This paper discusses how the COVID–19 pandemic can shift the conversation of paid and unpaid placements from an economic to a pedagogical and goodwill perspective. During the pandemic lockdown many placements were cancelled or postponed. Some continued as agreed but with students working from home, while other placements became unpaid. We build on the pertinent literature that raises legal, ethical, economic and pedagogical implications of paid versus unpaid placement models and what motivates placement organizations to offer placements. Four interdisciplinary trans-Tasman case studies are discussed to better understand the complex situations for placement organizations and universities to sustain WIL placements during this pandemic. Conclusions include recommendations to be vigilant and ensure goodwill is not used to mask the exploitation of students, but rather, positively influence the motivation behind offering placements during these trying times and beyond.