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The Army operates in an environment of ever increasing complexity. Traditional management models that have governed the actions of agencies and bureaucracies are becoming increasingly inadequate for dealing with the details and emergent realities of complex systems. The Army, like any other large government bureaucracy, must learn to adapt to the unfamiliar patterns of actions and products in a complex operating environment. How the Army responds to a complex environment is evident in its planning process. This paper seeks to illuminate what the Army intends when it plans and what it means to plan in a complex environment. The Army's effort to remediate the Year 2000 computer problem (Y2K) is an example of both. The Army's Action Plan for dealing with Y2K is the case study that this paper examines. It is a significant example of how the Army plans and provides insight into how the Army and the government understand planning in a complex environment. Through a series of performance controls, namely the Year 2000 database, the plan's timeline, and the Compliance Certification Checklist, the Action Plan is a method for controlling the process of Army Y2K remediation. While the Action Plan itself follows a traditional organizational model that places emphasis on monitoring outcomes and adherence to a schedule of action, subordinate agencies governed by the plan follow a different organizational model; one that reflects the experience of complex systems management. The difference between the two approaches provides an insight into what is necessary to adequately manage complex actions in complex systems: a type of control that allows an organization time to learn while it accomplishes its mission.