The macrocognitive workplace is constantly changing, and a work system can never match its environment completely; there are always gaps in fitness because the work is itself a moving target. This article looks at a domain where the workplace is a moving target in three ways: cyberdefense. New technology and work methods are continually being introduced, domain constraints are not constant; the work itself is changing in terms of its new goals and requirements, and anything can be surprising. The article presents a possible sensemaking strategy and implications for the design of intelligent systems founded on human-machine interdependence, semantically rich policy governance, and having the goal of achieving resilience in the cognitive work.