This study investigates the dynamics of urban resilience (UR) and sustainability (US) in Finnish regional planning cultures, focusing on the Helsinki‐Uusimaa and Southwest Finland regions. It highlights the intertwined nature of UR and US, emphasizing the need for clearer distinctions to enhance planning effectiveness. Through comparative case studies, this research explores the role of institutional planning culture in shaping procedural resilience amidst complex socio‐environmental changes. It reveals resource constraints as critical challenges, influencing decision‐making and collaboration across governance levels. Additionally, it underscores the importance of long‐term commitment and integrated regional visions for fostering sustainable development beyond electoral cycles. The paper advocates for an integrated approach to regional development, emphasizing the significance of addressing power dynamics and economic resilience alongside environmental considerations. Overall, it calls for a nuanced understanding of resilience‐sustainability interlinkages to craft more effective and adaptive planning strategies.