<p>AI decision-making systems are often criticized for creating Kafkaesque situations for the individuals who come in contact with them. In this article, we argue that neither AI nor the decision-making aspect of such systems is the common denominator for technology-enabled Kafkaesque situations. Based on a comparative look into three empirical case studies – New York Subway full-length turnstile systems, traditional call menu systems, and the appeal process for user-generated content – we propose that anti-communication lies at the heart of Kafkaesque technological services. Such anti-communication is preventing users from carrying out informed self-advocacy. We also note the difficulties of Kafkaesque technologies in coping with technical failures and their tendency to create orphan cases, and attribute much of the problem to the fact that these technologies are not designed to fail-safe. We conclude our analysis by arguing that technology developers are prone to creating Kafkaesque technologies and offering suggestions for combating this tendency.</p>