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Homebrew, OpenSSL and PowerShell

0 minute read #stuck #ssl #powershell #security

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

… but breaks basically any SSL-using software. So decide for yourself, I stopped using this hack.

References: