Pain can be considered as a signal of “bodily error”: Errors – discrepancies between the actual and optimal/targeted state – can put organisms at danger and activate behavioral defensive systems. If the error relates to the body, pain is the warning signal that motivates protective action such as avoidance behavior to safeguard our body’s integrity. Hence, pain shares the functionality of errors. On the neural level, an important error processing component is the error-related negativity (ERN), a negative deflection in the electroencephalographic (EEG) signal generated primarily in the anterior cingulate cortex within 100 ms after error commission. Despite compelling evidence that the ERN plays an important role in the development of various psychopathologies and is implicated in learning and adjustment of behavior, its relation to pain-related avoidance has not yet been examined. Based on findings from anxiety research, it seems conceivable that individuals with elevated ERN amplitudes are more prone to engage in pain-related avoidance behavior, which may, under certain conditions, be a risk factor for developing chronic pain. Consequently, this new line of research promises to contribute to our understanding of human pain. As in most novel research areas, a first crucial step for integrating the scientific fields of ERN and pain is developing a paradigm suited to address the needs from both fields. The present manuscript presents the development and piloting of an experimental task measuring both ERN and avoidance behavior in response to painful mistakes, as well as the challenges encountered herein. A total of 12 participants underwent one of six different task versions. We describe in detail each of these versions, including their results, shortcomings, our solutions, and subsequent steps. Finally, we provide some advice for researchers aiming at developing novel paradigms.