Behavioral readiness can take the form of communication and self-control skills during challenging situations that are correlated with the development of problem behavior. A skill-based approach can teach behavioral readiness using procedures that involve synthesized reinforcement, probabilistic reinforcement, and contingency-based delays; however, this approach is commonly used to address severe behavior under specific situations. There is limited research evaluating a skill-based approach to teaching behavioral readiness and addressing emerging problem behavior. Also, it is unclear whether teaching effects under specific situations transfer across other, functionally distinct, situations. We evaluated the generality of a skill-based approach by teaching skills systematically across primary challenging situations involving the interruption of play, presentation of instructions, and removal of reinforcers. Teaching increased communication and self-control skills, and most skills transferred to secondary challenging situations (treatment extension probes) and caregiver-implemented sessions. We discuss challenging situations that required teaching, the generality of teaching, and procedural considerations.