We propose an experimental method to study the possible emergence of sensemaking in artificial agents. This method involves analyzing the agent’s behavior in a test bed environment that presents regularities in the possibilities of interaction afforded to the agent, while the agent has no presuppositions about the underlying functioning of the environment that explains such regularities. We propose a particular environment that permits such an experiment, called the Small Loop Problem. We argue that the agent’s behavior demonstrates sensemaking if the agent learns to exploit regularities of interaction to fulfill its self-motivation as if it understood (at least partially) the underlying functioning of the environment. As a corollary, we argue that sensemaking and self-motivation come together. We propose a new method to generate self-motivation in an artificial agent called interactional motivation. An interactionally motivated agent seeks to perform interactions with predefined positive values and to avoid interactions with predefined negative values. We applied the proposed sensemaking emergence demonstration method to an agent implemented previously, and produced example reports that suggest that this agent is capable of a rudimentary form of sensemaking.