We are concerned with the implications and interactions of three common expressive extensions to classical planning: conditional plans, context-dependent actions, and nondeterministic action outcomes. All of these extensions have appeared in recent work, sometimes in conjunction, but the semantics of the combination has not been fully explored. As we have argued in previous work, providing a coherent semantics for conditional planning with context-dependent actions requires that the planner’s information state be modeled separately from the world state. In this paper, we present a new planning language, WCPL, encompassing these extensions. The semantics of WCPL includes an explicit treatment of the planner’s information state as knowledge, as opposed to some form of context labelling. In addition to clarifying and unifying a disparate set of results from earlier work, we extend that work: WCPL handles both conditional and fail-safe plans for an action representation including both context-dependent and nondeterministic actions.