This paper examines the role of proprietary software in the production of open educational resources (OER). Using a single case study, the paper explores the implications of removing proprietary software from an OER project, with the aim of examining how complicated such a process is and whether removing such software meaningfully advances a critical approach to OER. The analysis reveals that software from the Big Five technology companies (Apple, Alphabet/Google, Amazon, Facebook and Microsoft) are deeply embedded in OER production and distribution, and that complete elimination of software or services from these companies is not feasible. The paper concludes by positing that simply rejecting Big Five technology introduces too many challenges to be justified on a pragmatic basis; however, it encourages OER creators to remain critical in their use of technology and continue to try to advance a critical approach to OER.