The use of fieldwork experiences has been widely accepted by teachers of evaluation as a method of preparing future practitioners for challenges encountered in the field. However, several challenges must be addressed to make fieldwork experiences a useful tool in preparing students for their professional careers. The authors present a case study in which a graduate student in an evaluation class approached an agency seeking a fieldwork project. The experience was not positive. Both a student's and an instructor's perspectives are offered in understanding the reasons for the negative experience. Suggestions are provided from both perspectives as to how the experience could have been improved. The article is intended as a teaching tool to be provided by instructors to students seeking applied experiences before approaching agencies. This article provides an opportunity for student evaluators to learn from the experiences of another student; likewise, the instructor in this case study provides insights that other instructors of evaluation may find helpful.