This study concerned aspiring educational leaders’ problem-solving skill development, specifically through classroom instruction with real-world scenarios. Professional educators obtaining an advanced degree in educational administration at a public university were surveyed in the fall and spring about their problem-solving abilities. Participants were also asked to respond to real-world principal scenarios. Focus group interviews were conducted in the spring. Results indicated that participants’ confidence in their problem-solving abilities did improve, though their ability to address the real-world problems did not improve significantly. Participants identified the value of learning from real-world scenarios and professors who had experience as administrators, and they also recognized the importance of learning from one another during discussions of the scenarios. Participants indicated that they still needed experience working in actual administrative contexts.