How to install brew packages based on XCode, Ruby, Homebrew
- About Homebrew
- Preparations: XCode CLI
- Install Homebrew
- Upgrade brew formulas
- Brew Cask Install
- Analytics off
- Debian apt-get
- Social media
- More on OSX
This tutorial provides a deep dive of Homebrew, a package manager for Mac OSX (MacOS) like Chocolatey for Windows, apt-get for dpkg, or yum for RPM.
Step-by-step instructions are provided here to install Homebrew itself and then install Homebrew packages based on the name of formulae specified for installation in a command such as:
brew install wget
DEFINITION: A formula provides instructions on how to install packages and their dependencies, such as where to find tar.gzip files for download.
Brew installs packages in its own Cellar directory (folder) and adds symlinks to the /usr/local folder.
Homebrew is the newest and most popular package utility on OSX.
Alternatives to Homebrew:
sudo port install tree
Homebrew’s web page is at http://brew.sh
Preparations: XCode CLI
Make a full backup of your system right before following these instructions.
Open the App Store to install XCode, Apple’s IDE for developing Swift and Objective-C to run on iPhones and iPads.
PROTIP: Apple’s App Store only installs .app files. So programs invoked from the command line Terminal (such as gcc) need to be installed a different way.
To verify XCode CLI install:
This message means that it’s not installed:
xcode-select: error: tool 'xcodebuild' requires Xcode, but active developer directory '/Library/Developer/CommandLineTools' is a command line tools instance
Open a Terminal to install XCode CLI:
If XCode is not already installed, you are prompted to install it:
Installation is to folder: /Library/Developer/CommandLineTools/.
Homebrew requires OS X 10.5+ and the Xcode command line tools.
To download the Command Line Utilities, go to https://developer.apple.com/download/more/ and look for your version of “Command Line Tools (macOS 10.14) for XCode 10”, one that doesn’t say “beta”.
Since the El Capitan version of Mac OSX, file permissions in /usr/local have changed, causing error messages such as:
The linking step did not complete successfully The formula built, but is not symlinked into /usr/local
xcrun: error: invalid active developer path (/Library/Developer/CommandLineTools), missing xcrun at: /Library/Developer/CommandLineTools/usr/bin/xcrun
So in a Terminal shell window at any folder:
sudo chown -R :staff /usr/local
Verify installation by getting the version of the GNU Compiler Collection:
You should see something like this (for Mojave):
Configured with: --prefix=/Library/Developer/CommandLineTools/usr --with-gxx-include-dir=/Library/Developer/CommandLineTools/SDKs/MacOSX10.14.sdk/usr/include/c++/4.2.1 Apple LLVM version 10.0.0 (clang-1000.10.44.4) Target: x86_64-apple-darwin18.2.0 Thread model: posix InstalledDir: /Library/Developer/CommandLineTools/usr/bin
Homebrew makes use of Ruby, which comes with macOS.
Install Homebrew if you haven’t already.
ruby -e "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/master/install)"
CAUTION: Don’t press Enter on the Terminal until the Download Software dialog reaches 100%.
Press the Enter key to the message:
Press RETURN to continue or any other key to abort. then
To proceed, enter the root password, or type Ctrl+C to abort.
NOTE: The download is from
HISTORICAL NOTE: Previously, the Homebrew installer was at
Identify where the Homebrew program itself is located:
The response is the brew executable program at:
The “brew” above is a shell script file.
PROTIP: The “/usr/local” is the default specified by the $HOMEBREW_PREFIX enviornment variable.
Identify where the Homebrew program stores packages:
Update Homebrew itself
Get Homebrew version:
The response (at time of writing) indicates Homebrew is not “v1.0” yet:
Homebrew 0.9.9 (git revision e9cc; last commit 2016-06-12) Homebrew/homebrew-core (git revision 3977; last commit 2016-06-12)
NOTE: Homebrew is open-sourced at
To update Homebrew itself and its formulas:
Yes, run it twice to make sure all dependencies took.
Each run can take several minutes.
### Search for a formula to install #
Use an internet browser (such as Google Chrome) to view formula defined in
Install the wget command-line utility by formula name (for example, wget):
brew install wget
This installs to folder /usr/local/bin/wget.
See Tips & Tricks on how to use proxy, remove the beer mug emoji, highlighting within editors, etc.
Get a count of kegs, how many files, and the disk space they take:
brew info --all
A sample response:
15 kegs, 18,528 files, 540.6M
Where did it go?
List where .tar.gz “bottle” files are downloaded into from the internet:
DEFINITION: A “Bottle” is a pre-built binary Keg used for installation instead of building from source. It can be unpacked.
The response includes your user name, which enables Homebrew to work without using sudo (elevation to root).
The equivalent of the above is:
List bottles downloaded:
Examples of responses:
autoconf-2.69.el_capitan.bottle.4.tar.gz maven-3.3.9.tar.gz awscli-1.10.44.el_capitan.bottle.tar.gz node-6.2.2.tar.xz docker-1.11.2.el_capitan.bottle.tar.gz openssl-1.0.2h_1.el_capitan.bottle.tar.gz gimp-2.8.16-x86_64.dmg pkg-config-0.29.1.el_capitan.bottle.tar.gz libgpg-error-1.23.el_capitan.bottle.tar.gz readline-6.3.8.el_capitan.bottle.tar.gz libksba-1.3.4.el_capitan.bottle.tar.gz
List brew formulas installed:
The alternative commands above all do the same thing of the same folder, for example:
autoconf awscli libgpg-error libtool maven node pkg-config xz automake docker libksba libyaml mysql openssl readline
There is no response if no brew package has been installed.
See one level below one of the above folders for a specific formula, such as openssl:
It is usually a version number, such as:
DEFINITION: A “Keg” is the installation prefix of a formula, such as:
List brew package .rb (Ruby language) files installed:
The response is a long list.
List brew package folders:
The response is a long list.
Different ways to install weget.
The above is one of several ways to install the wget command-line utility.
One way is to install Apple’s Xcode.
brew install --build-from-source wget
Test wget operating:
Verify brew installation:
If you see this message at the top of messages returned:
Warning: Unbrewed header files were found in /usr/local/include. If you didn't put them there on purpose they could cause problems when building Homebrew formulae, and may need to be deleted.
The above may occur if curl and nodejs were installed without using homebrew.
Remove them before installing node and curl using Homebrew:
rm -rf /usr/local/include/node/
Create symlinks to installations performed manually in Cellar. This allows you to have the flexibility to install things on your own but still have those participate as dependencies in homebrew formulas.
First, see what exactly will be overwritten, without actually doing it:
brew link --overwrite --dry-run openssl
The response is:
Warning: openssl is keg-only and must be linked with --force Note that doing so can interfere with building software.
“Keg-only” refers to a formula installed only into the Cellar and not linked into /usr/local, which means most tools will not find it. This is to avoid conflicting with the system version of the same package.
Alternately, if aswcli is specified for dry-run, the response is:
Warning: Already linked: /usr/local/Cellar/awscli/1.10.44 To relink: brew unlink awscli && brew link awscli
NOTE: Homebrew installs to the Cellar it then symlinks some of the installation into /usr/local so that other programs can see what’s going on.
A symlink to the active version of a Keg is called an “opt prefix”.
List where a link goes:
ls -l $(which wget)
/usr/local/bin/wget -> /usr/local/Cellar/wget/1.18/bin/wget
If you see this message:
Warning: Broken symlinks were found. Remove them with `brew prune`:
A sample response:
Pruned 1598 symbolic links and 185 directories from /usr/local
List formula (package definitions):
brew edit $FORMULA
The above command brings you to your default text editor (vim or whatever is specified in the $EDITOR variable).
Type :q to quit out.
Upgrade brew formulas
List brew packages that are obsolete:
To stop a specific package from being updated/upgraded, pin it:
brew pin $FORMULA
$FORMULA is ???
To allow that formulae to update again, unpin it.
Download and update ALL software packages installed:
To see which files would be removed as no longer needed:
brew cleanup -n
No response if there is nothing to clearn.
To really remove all files no longer needed:
A sample response:
Removing: /Users/mac/Library/Caches/Homebrew/mariadb-10.1.14.el_capitan.bottle.tar.gz... (36.6M) ==> This operation has freed approximately 36.6M of disk space.
Brew tap adds repos not in the Homebrew master repo from inside a larger package.
https://github.com/Homebrew/brew/blob/master/docs/brew-tap.md says tap adds to the list of formulae that brew tracks, updates, and installs from.
List brew tap packages already installed:
Install the ip tool included with iproute2 on Linux:
brew tap brona/iproute2mac brew install iproute2mac
The command specififies the account and repo in GitHub, as in
ifconfig en0 | grep inet | grep -v inet6 | cut -d ' ' -f2
Try it (instead of ifconfig):
ip ip addr show en0
Remove a tap:
brew untap brona/iproute2mac
Brew Cask Install
Homebrew cask extends homebrew and brings its elegance, simplicity, and speed to MacOS (OS X) GUI applications and large binaries.
With Cask, you can skip the long URLs, the “To install, drag this icon…”, and manually deleting installer files.
Temporarily set the permissions on /usr/local:
sudo chown $USER /usr/local
Install brew cask:
brew tap caskroom/cask brew install brew-cask
Applications are kept in their Caskroom under /opt and symblinked to $HOME/Applications from
https://caskroom.github.io, the home page, said there are 3,197 casks as of June 5, 2016.
QUESTION: Is there a graph of growth in cask counts over time?
Install the cask extension to Homebrew:
brew tap caskroom/cask
ruby -e "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/master/install)" < /dev/null 2> /dev/null ; brew install caskroom/cask/brew-cask 2> /dev/null
Search for a cask by name, in website is where casks are obtained:
Alternately, run a search command. This example searches for “yo”:
brew cask search yo
PROTIP: One should see the cask definition before using it. I would be suspicious of casks with sparse information.
The safe way to get the homepage URL of the programmer is from here (don’t Google it and end up at a rogue site).
Look at some cask definitions:
https://github.com/caskroom/homebrew-cask/blob/master/Casks/google-chrome.rb is a sample cask definition:
Install the cask:
brew cask install google-chrome
Cask downloads then moves the app to the ~/Applications folder, so it can be opened this way:
Open the installed cask from Terminal:
open /Applications/"Google Chrome.app"
Installing with cask enables you to cleanup:
brew cask cleanup
If you get an error about “permissions denied”:
Create a Caskroom folder
cd ~ mkdir Caskroom
Edit the .bash_profile
Add this line:
export HOMEBREW_CASK_OPTS="--appdir=~/Applications --caskroom=~/Caskroom"
QUESTION: The use of –caskroom is deprecated?
- Save the file.
Restart the terminal.
Homebrew now defaults to retrieving behavioral analytics tracking. Although anonymized, you may not want to participate in that. To disable the extra network traffic:
brew analytics off
Download Fink commander Fink Installer.pkg from
This explains: Fink stores data in the directory “/sw” by default. This goes against the Filesystem Hierarchy Standard’s recommendation to use “/usr/local”. Within Fink’s directory, a FHS-like layout (/sw/bin, /sw/include, /sw/lib, etc.) is used.
For more documentation on brew, look here and:
Social media from brew’s readme:
- @MacHomebrew on Twitter
- IRC freenode.net#machomebrew
- Email firstname.lastname@example.org
- Read archive of emails at https://groups.google.com/forum/#!forum/homebrew-discuss
More on OSX
This is one of a series on Mac OSX:
- MacOS Hardware and accessories
- MacOS Boot-up
- MacOS Terminal Tips and Tricks
- MacOS Keyboard tricks
- Text editors and IDEs on MacOS
- MacOS Setup automation
- MacOS Homebrew installers
- Manage Disk Space on MacOS
- Data Backups on MacOS
- Ports open
- Applications on MacOS
- Windows on Apple MacOS
- Packer create Vagrant Windows image
- Python on MacOS
- Maven on MacOS
- Ruby on MacOS
- Java on MacOS
- Node on MacOS installation
- PHP on MacOS
- Scala ecosystem