Purpose: Conditional use of communication skills refers to the ability of a learner to appropriately generalize and discriminate when, where, and how to communicate based on constant variation and shifts in environmental cues. Method: We describe discrimination and generalization challenges encountered by learners with complex communication needs and ways in which these challenges are fostered through traditional communication intervention programming. We address arrangements in instruction that maximize the probability of learners acquiring the conditional use of new vocabulary and the modest instructional technology implemented when planning for generalization. Results: We propose establishing well-discriminated and generalized use of new vocabulary items through the application of a general case instruction framework to communication intervention programming. Conclusion: We provide intervention methodology, including intervention steps for general case instruction, a plethora of functional examples, and graphic displays to assess and intervene to promote conditional use of communication skills for learners with complex communication needs.