Given what is known about the importance of productive struggle for supporting student learning of mathematics at all levels, the current study sought to examine teacher attitudes towards student struggle when students learn mathematics in remote learning settings compared with classroom settings. Eighty-two Australian early years primary teachers involved in a professional learning initiative focused on teaching mathematics through sequences of challenging tasks completed a questionnaire inviting them to compare the two settings. Drawing on a mixed-methods approach, we found that teachers were more positive about the value of student struggle in classroom-based settings compared with remote learning settings. Qualitative analysis of open-ended responses revealed four themes capturing why teachers viewed efforts to support productive struggle in a remote learning setting as potentially problematic: absence of a teacher-facilitated, synchronous, learning environment; parents' negative attitudes towards struggle when learning mathematics; lack of social connection and peer-to-peer collaboration; and difficulties accessing learning materials. Suggestions for mitigating some of these challenges in the future are put forward.