When can we trust that a system that has performed well in the past will continue to do so in the future? Designing systems that are reliable in the wild is essential for high stakes applications such as self-driving cars and automated surgical assistants. This workshop aims to bring together researchers in diverse areas such as reinforcement learning, human-robot interaction, game theory, cognitive science, and security to further the field of reliability in machine learning. We will focus on three aspects — robustness (to adversaries, distributional shift, model misspecification, corrupted data); awareness (of when a change has occurred, when the model might be miscalibrated, etc.);and adaptation (to new situations or objectives). We aim to consider each of these in the context of the complex human factors that impact the successful application or meaningful monitoring of any artificial intelligence technology. Together, these will aid us in designing and deploying reliable machine learning systems.