Install Homebrew + Cask Mac (Older)

You probably need to:

  • install XCode CLI Tools (which can be difficult on older versions)
  • update OpenSSL
  • upgrade git

Install XCode CLI Tools

You can use a helper shell script to do this for you. The source comes from this gist. Alternatively, view its source, follow the code, and find your corresponding version of XCode CLI Tools and install accordingly.

Copy + Paste

If you don’t have a new enough version of OpenSSL, you won’t be able to download the script with wget or curl, so just open the link manually in a web browser and save the file with the same name below, on your Desktop.

From a Terminal session:

  • (if able, per note above) curl -O https://gist.github.com/rtrouton/f92f263414aaeb946e54/raw/9ac37d561c38d54ff7fc31dee66e89d10fc3e2b9/gistfile1.sh
  • mv gistfile1.sh xcode-cli-tools-install.sh
  • chmod +x xcode-cli-tools-install.sh
  • sudo sh xcode-cli-tools-install.sh

This script when run, the last line, will download the installer package, perform the install, and remove the dmg once finished.

Updating OpenSSL

1. Install Mac Ports

2. Install OpenSSL from Mac Ports

You can confirm your current version of OpenSSL with the command openssl version.

Install the latest version from Mac Ports with:

sudo port install openssl

Upgrade Git

Download and install the latest version of Git for Mac from git-scm.com.
https://git-scm.com/download/mac

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