This study examined the problem posing strategies of pre-service primary school teachers in different problem posing situations (PPSs) and analysed the issues they encounter while posing problems. A problem posing task consisting of six PPSs (two free, two structured, and two semi-structured situations) was delivered to 40 participants. Participants were allowed 30 minutes to complete this task. Of the 40 pre-service primary school teachers that participated in the study, 10 were selected for interview. Interviews took 25-30 minutes and were video-taped and transcribed. The data obtained from the study were then analysed using content analysis. The presented results showed that pre-service primary school teachers used different strategies in free, semistructured, and structured PPSs and encounter a range of issues when tackling them.