In 2017, Portugal lived through its most infamous extreme wildfire season with 117 fatalities, hundreds of injured people, 3588 destroyed structures, an official cost of 1456 million euros, and 539,920 ha of burned area. Among the legislative and institutional changes prompted by the 2017 events, the “Safe Village” and the “Safe People” programs were established in 2018 (Council of Ministers Resolution no. 157-A/2017) with the purpose of: (i) implementing structural measures to protect people, goods, and buildings in the wildland–urban interface and (ii) developing awareness-raising actions on the prevention of risk behavior and self-protection measures aimed at specific audiences. There is interest in understanding how this program has been implemented, in identifying the strengths and barriers to its implementation, and in evaluating how this program is changing attitudes and behaviors of homeowners in wildfire risk reduction and preparedness as well as in coping with a wildfire. An online survey was sent, between November 2021 and June 2022, to the 139 municipalities that implemented the programs. The response rate was 81% (112 municipalities). To understand the involvement of citizens in this program and its efficacy, we surveyed 51 homeowners in 5 villages in the north and center of Portugal. Our results highlight distinctive local and contrasting dynamics of the programs, related with the interest of local authorities on their implementation and maintenance, and in citizens’ involvement. Recognizing the importance in reducing wildfire risk and improving the citizens’ safety, recommendations on the legal context, the characteristics of the programs, and implementation and maintenance procedures are proposed. They are aimed at enhancing the efficacy in different geographical contexts, namely, proposing initiatives that are much beyond the scope of the “Safe Village” and “Safe People” programs.