@dean-houston By way of follow up, unfortunately the verbose output of an apt update against the jenkins repo provided exactly 0 clarity. apt update -o Debug::Acquire::http=true Ign:1 https://pkg.jenkins.io/debian-stable binary/ InRelease Hit:2 https://pkg.jenkins.io/debian-stable binary/ Release Reading package lists... Done Building dependency tree... Done Reading state information... Done All packages are up to date. I appreciate the help in trying to make this work, but I am going to punt on this and just grant the specific server access directly to pkg.jenkins.io.