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You can use my modified repository of OpenSSL v1.0.1j made to work with compiling on the M1 chip from Apple. Some may ask why would you want the old version of OpenSSL? Some applications are dependent upon it, but only do this if you know what you are doing. Repo: https://github.com/carsenk/openssl10-darwin-arm git clone https://github.com/carsenk/openssl10-darwin-arm cd openssl10-darwin-arm ./configure darwin64-arm64-cc no-asm make sudo make install sudo ln -sf /usr/local/ssl/bin/openssl `which openssl` You can then run openssl version to confirm you are running legacy OpenSSL v1.0.1j on the Apple Silicon M1 chip!