Community repositories, such as Docker Hub, PyPI, and RubyGems, are bustling marketplaces that distribute software. Even though these repositories use common software signing techniques (e.g., GPG and TLS), attackers can still publish malicious packages after a server compromise. This is mainly because a community repository must have immediate access to signing keys in order to certify the large number of new projects that are registered each day. This work demonstrates that community repositories can offer compromise-resilience and real-time project registration by employing mechanisms that disambiguate trust delegations. This is done through two delegation mechanisms that provide flexibility in the amount of trust assigned to different keys. Using this idea we implement Diplomat, a software update framework that supports security models with different security / usability tradeoffs. By leveraging Diplomat, a community repository can achieve near-perfect compromise-resilience while allowing real-time project registration. For example, when Diplomat is deployed and configured to maximize security on Python’s community repository, less than 1% of users will be at risk even if an attacker controls the repository and is undetected for a month. Diplomat is being integrated by Ruby, CoreOS, Haskell, OCaml, and Python, and has already been deployed by Flynn, LEAP, and Docker.