This study investigates and prioritizes the factors associated with the underperformance of local contractors in Sistan and Baluchestan Province, Iran, in delivering construction projects and managing contracting businesses. Contractor performance is considered at both project and firm levels, including schedule, cost, quality, contractual compliance, financial stability, business continuity, and competitiveness. A quantitative, descriptive–analytical survey was conducted using responses to a researcher-developed questionnaire. The dataset comprised 50 completed questionnaires and 44 core items covering seven explanatory dimensions: managerial; financial and economic; technical and operational; human resources; contractual and legal; environmental and social; and institutional and stakeholder-related factors. Internal consistency was high, with a Cronbach’s alpha of 0.987 for the 44 core items. Because the construct scores deviated significantly from normality, Spearman’s rank correlation and the Friedman test were used. All seven dimensions were positively and significantly associated with contractor underperformance (p < 0.001). Contractual and legal factors showed the strongest association (ρ = 0.813), followed by technical and operational factors (ρ = 0.798) and financial and economic factors (ρ = 0.765). In contrast, environmental and social factors received the highest average rank in perceived severity, followed by institutional and stakeholder-related factors and human-resource factors. These findings indicate that contractor underperformance is multidimensional: contextual constraints are widely perceived, while contractual and legal problems have the closest statistical association with underperformance in this sample. The results support integrated interventions involving contract administration, technical capacity, cash-flow management, workforce development, stakeholder coordination, and region-sensitive support for local contractors. Since the study is based on 50 respondents and correlational analyses, the findings should not be interpreted as evidence of causation.