While both practitioners and the public regard character strengths positively, some psychologists and philosophers harbor skepticism. In this analytical commentary on current research and literature, we trace such skepticism to a premature focus on positive outcomes, which eclipsed the theoretical groundwork outlined in the 2004 handbook. We propose solutions to ten key issues which, in our estimation, not only sustain this skepticism but also hinder meaningful advancement in the field of character strengths research: (1) Criteria evaluation, (2) Virtue functions, (3) Situational affordances, (4) Content validity, (5) Criterion validity, (6) Fulfillment conceptualization, (7) Adverse outcome modeling (8) Moral excellency, (9) Strengths conservatism, and (10) Methodological mainstream thinking. We contend that resolving these issues is necessary to uphold the standing of character strengths and positive psychology among its counterparts, and to establish a potent foundation for effective character development.