Modern privacy regulations provide a strict mandate for data processing entities to implement appropriate technical measures to demonstrate compliance. In practice, determining what measures are indeed "appropriate" is not trivial, particularly in light of vague guidelines provided by privacy regulations. To exacerbate the issue, challenges arise not only in the implementation of the technical measures themselves, but also in a variety of factors involving the roles, processes, decisions, and culture surrounding the pursuit of privacy compliance. In this paper, we present 33 challenges faced in the implementation of technical measures for privacy compliance, derived from a qualitative analysis of 16 interviews with privacy professionals. In addition, we evaluate the interview findings in a survey study, which gives way to a discussion of the identified challenges and their implications.

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