The benefits of risk management in the context of project portfolios have been widely recognized in the literature. However, approaches that assess the risk of organizational development project portfolios from the perspective of how the portfolio delivers value to the parent organization remain largely unexplored. To address this gap, our research takes a constructivist approach and an organizational perspective on project portfolios. We conducted twenty-eight semi-structured interviews and used thematic analysis to identify and relate four themes of a comprehensive project portfolio risk assessment (PPRA) framework: "project portfolio as the organizational unit for PPRA"; "organizational capabilities as portfolio outcomes in which PPR can be assessed"; "project portfolio levels as sources of risk factors in PPRA"; and "balance between project portfolio attributes complexity". Within the framework of organizational development project portfolios, this study contributes to our understanding of PPRA by providing two propositions: (1) The capabilities to be generated by the project portfolio can be used as the portfolio primary results on which PPRA can assess the risk of the project portfolio, establishing the impact of PPR on the project portfolio value delivering to the parent organization, and (2) The risk factors that impact the project portfolio expected results can be represented into PPRA as ‘output-related’ risk factors and ‘outcome-related’ risk factors.