The case is presented of an 8-year-old boy who was referred for psycho-educational assessment because of difficulties with writing. The article provides an example of the way in which a case unfolds as further assessment data become available, and describes a number of challenging aspects of the assessment process. In this case, dilemmas arose when test results were inconsistent at different time points, and when the results were inconsistent with clinical observations. The case report illustrates the ways in which practitioners can collaborate to make sense of such discrepancies, with each contributing a slightly different perspective or set of skills that, in combination, assist to better understand a child's difficulties.