Configure a Fresh Mac for Development

You have a fresh install of Mac OS X Catalina, and all the latest updates installed. Now you want to do some web development with Ruby on Rails. I am writing this as a reference for myself, because I go through this process frequently. Installations Core Setup Login to iCloud Install Apps from App Store Install iTerm2 Install Franz and Telegram Install homebrew (which will also auto-install Appleā€™s “command line developer tools”) and some packages

Upgrade to Catalina with Homebrew, Ruby, & Java

I upgraded to Catalina, with Homebrew & Ruby, and this is how I did it flawlessly. Prepare If you don’t already have homebrew installed, do that first. Install all Software Updates available in the Apple Menu, up to and including Catalina. Hardware Haven’t had any hardware issues yet. Software In order… Xcode The upgrade will erase your previous XCode install. (Optional) (re)Install XCode from the App Store first. The XCode Command Line Tools will actually install fine even without XCode.

Upgrade to El Capitan with Homebrew, Ruby, qt5, & Java

I upgraded to El Capitan, with Homebrew & Ruby, and this is how I did it flawlessly. … and Xcode and Java, etc. Prepare If you don’t already have homebrew installed, do that first, so you don’t have to deal with SIP issues. Install all Software Updates available in the Apple Menu, up to and including El Capitan. Hardware After the installs and forced reboots my 27” Thunderbolt display wouldn’t display anything.