Forest fires, i.e., wildfires, often cause an inevitable strain on society and human living conditions. Incident Commanders (IC) at the Fire and Rescue Services (FRS) are challenged to handle forest fires and at the same time address the forest owners’ needs; this stipulates a need for collaboration, information, and communication. Hence, the aim of this study was to explore and describe the ICs’ experiences and actions in their interactions with forest owners during forest fires on private property. Interviews were conducted and analyzed using Flanagan’s Critical Incident Technique (CIT) to describe the experiences and actions of 22 ICs. The results showed that a firefighting operation needs clarity in information exchange with the forest owner as a stakeholder, not a victim. The trust between forest owner and IC accelerated the operational phase. The ICs demonstrate more care than the law stipulates, and they worry about the forest owners. Therefore, the FRS needs to form a strategic partnership with forest owners and their network on a local level. Also, future forest fire drills should not only include emergency stakeholders (i.e., police, ambulance, etc.) but also forest owners and local volunteer organizations. For a resilient community, FRS and forest owner collaboration is vital.