This current study focuses on exploring expectations of World Wide Opportunities on Organic Farming (WWOOF) hosts and volunteers participating in various countries using online semi-structured interview method. Using psychological contract theory, motivation is discovered as playing an important role in the formation of expectations of 27 hosts and 20 volunteers. When comparing motivation of both groups, they display contrast, similarity and complementarity. Expectations as contents of the psychological contract of hosts and volunteers are both transactional and relational in nature. The transactional aspect include work, food, accommodation and learning opportunities while the relational aspect involve social life and cultural exchange. Both hosts and volunteers view communication as mutual obligation and one of the main challenges of their exchange relationship. The psychological contract of hosts and volunteers include their relationship with their respective WWOOF organizations. Communication from these organizations influences the formation of expectations of hosts and volunteers. Finally, all hosts and volunteers who were motivated to continue cited the benefits they gained from the woofing experience in the form of met expectations and unexpected positive outcomes. In contrast, perceived breach and violation of their psychological contract as described through self-reported accounts may lead to shortening of hosting and early withdrawal from volunteering. Hosts respond to violation of contract by requesting their volunteers to leave.