The specific issue here (Windows .zip nightlies being old) was introduced when we transitioned Windows CI from Buildbot to Buildkite. During the transition, we lost the .zip uploads (but retained the .tar.gz uploads).
This issue will be fixed by the following PR: [windows] Upload `.zip` files by staticfloat · Pull Request #245 · JuliaCI/julia-buildkite · GitHub
@gitboy16 Thanks for reporting this issue!