The Debian project is one of the largest free software undertakings worldwide. It is geographically distributed, and participation in the project is done on a voluntary basis, without a single formal employee or directly funded person. As we will explain, due to the nature of the project, its authentication needs are very strict—User/password schemes are way surpassed, and centralized trust management schemes such as PKI are not compatible with its distributed and flat organization; fully decentralized schemes such as the PGP Web of Trust are insuficient by themselves. The Debian project has solved this need by using what we termed a “curated Web of Trust”.We will explain some lessons learned from a massive key migration process that was triggered in 2014. We will present the social insight we have found from examining the relationships expressed as signatures in this curated Web of Trust, some recommendations on personal key-signing policies, and a statistical study and forecast on aging, refreshment and survival of project participants stemming from an analysis on their key-handling.