Climate Action Planning (CAP), intended as a structured process to reduce greenhouse gas emissions and enhance resilience to climate change, has expanded rapidly, yet significant gaps remain at the municipal level, where plans often struggle to translate into concrete actions. Municipalities play a central role in CAP because many key decisions related to spatial planning, building regulations, mobility, tourism, and hazard zoning are taken at this scale. However, limited administrative capacity, financial constraints, and institutional fragmentation often hinder effective climate action. Although barriers to adaptation are conceptually well established, empirical evidence on how they are perceived and addressed in practice remains limited. This study examines barriers encountered by six territories in Lombardy, Italy, ranging from mountain communities to peri-urban areas and mid-sized cities, that have developed their Climate Action Strategies (CASs). The analysis follows three steps: (1) identifying barriers reported by project managers and comparing them with those described in the literature; (2) classifying CAS actions into thematic categories and assessing their responsiveness to the identified barriers; and (3) analyzing barrier–action linkages alongside budget allocations to uncover recurring patterns, gaps, and structural misalignments. The findings show that institutional barriers constitute systemic, cross-cutting constraints across all cases. Mountain territories face stronger informational and financial limitations, while peri-urban areas exhibit hybrid governance and ecological challenges. Overall, the barriers identified through the questionnaire closely mirror those documented in the literature, and there is strong ex post alignment between perceived barriers and planned actions. However, financial resources remain disproportionately concentrated in infrastructure-intensive measures, leaving transversal, enabling actions (e.g., governance, monitoring, participation, capacity-building) comparatively underfunded.