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: