The obstacles facing decision making in Agile development are critical yet poorly understood. This research examines decisions made across four stages of the iteration cycle: Iteration Planning, Iteration Execution, Iteration Review and Iteration Retrospective. A mixed method approach was employed, whereby a focus group was initially conducted with 43 Agile developers and managers to determine decisions made at different points of the iteration cycle. Subsequently, six illustrative mini cases were purposefully conducted as examples of the six obstacles identified in these focus groups. This included interviews with 18 individuals in Agile projects from five different organizations: a global consulting organization, a multinational communications company, two multinational software development companies, and a large museum organization. This research contributes to Agile software development literature by analyzing decisions made during the iteration cycle and identifying six key obstacles to these decisions. Results indicate the six decision obstacles are unwillingness to commit to decisions; conflicting priorities; unstable resource availability; and lack of: implementation; ownership; empowerment. These six decision obstacles are mapped to descriptive decision making principles to demonstrate where the obstacles affect the decision process. The effects of these obstacles include a lack of longer-term, strategic focus for decisions, an ever-growing backlog of delayed work from previous iterations, and a lack of team engagement.