This article uses the story of a multi-year project conducted in four countries in east central and southeastern Europe to illustrate the challenges faced by an evaluator working in a social, political, and cultural context different from her own. Situations involving divergent expectations and unexpected events created circumstances where the evaluator had to shift roles and approaches to ensure the evaluation could remain on course. The evaluation was deemed problematic at various stages of implementation and more successful at other times. In 2010, 6 years after its completion, questions linger as to the degree the evaluation was indeed "successful."