On Mac, PowerShell really, really wants to specifically use OpenSSL version 1.0. Unfortunately, homebrew switched to OpenSSL version 1.1 in v2.2, because OpenSSL 1.0 is end-of-life. This fixes it (for now at least): brew uninstall openssl –ignore-dependencies brew uninstall openssl –ignore-dependencies brew install https://github.com/tebelorg/Tump/releases/download/v1.0.0/openssl.rb References: My comment on GitHub
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