Self-assessment is important in student and professional development. This study evaluated the impact of a structured electronic portfolio program that provided primarily global feedback on pharmacy students' self-assessment skills related to five general outcomes over a two-year period. The self-assessed outcomes, common to many academic programs, were communication/cultural competence, critical thinking/problem solving, evidence-based practice, professionalism/leadership, and teamwork/inter-professional collaboration. The primary outcome measure was a change in scores for each outcome from the students' earliest gradable submission to their latest over a two-year period, using a scoring rubric (maximum = 21 points) to evaluate self-assessment quality. Mean scores improved significantly for all outcomes. From the earliest to latest portfolio submissions across all longitudinal outcomes, rubric scores improved in 61% of submissions, remained the same in 16%, and decreased in 23%. A total of 141 submissions (41%) had a score increase of two or more points, with 45 entries (13%) increasing by > four points. Only 37 (11%) had a decrease in score of two or more points, with just nine entries (3%) showing a decrease of > four points. This article describes a unique portfolio program to develop students' self-assessment skills, including improvements that can be extrapolated to students across many academic disciplines.