When comparing pkgsrc vs Homebrew Cask, the Slant community recommends Homebrew Cask for most people. In the question“What are the best Mac package managers?” Homebrew Cask is ranked 2nd while pkgsrc is ranked 6th. The most important reason people chose Homebrew Cask is:
Homebrew Cask adds functionality to Homebrew such as allowing downloads of commercial licensed apps.
Specs
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Pros
Pro pkgin is an apt-like tools for installing binaries from pkgsrc
pkgin aims to be a tool similar to apt/yum for managing pkgsrc binaries by relying on pkg_summary for installing, removing and upgrading packages and dependencies, using a remote repo.
Pro Adapted for use on over a dozen different operating systems
Has been adopted to be used on several Unix-like operating systems and Windows. It's also the default package manager of DragonflyBSD and of the (now discounted) Bluewall Linux distro.
Pro Installs and works in the same way as MacPorts
Installs its own dependencies which means that it is very secure. Cannot install anything unless you use the "sudo" command which is in keeping with the Unix philosophy.
Pro Both binary packages and source build possible
Fast software installation is possible by using binary packages. It's also easy to build from source which allows for different compile-time options (like different UI backends) as well as gaining access to pre-release versions of software in certain cases.
Pro Offering tooling for backporting fixes
Backporting fixes can be done by cherry-picking updates from a newer branch (pkgsrc is released every 3 months) and creating a package. Sometimes bugs need to be fixed for production and there is neither a fix in newer pkgsrc nor the softwares upstream. So pkgsrc has tools like pkgdiff, mkpatches, etc. that help with developing patches and building binary packages from that. A bit of documentation about that process can be found here.
Pro Does not need Xcode command line tools or Xcode.
This means that you can install it fresh on a new installation of MacOS and have all your favorite apps installed right from the start.
Pro Works easily with Ansible
Can be used from within Ansible to install packages on macOS.
Pro Easy installation if you use 3rd party scripts
This one works brilliantly.
Pro Extends Homebrew
Homebrew Cask adds functionality to Homebrew such as allowing downloads of commercial licensed apps.
Pro "Zap" application configuration
this is an interesting feature allowing user to remove application configuration leftowers
Pro Manage graphical applications through the command line
Homebrew Cask allows you to install graphical applications through the command line, rather than having to go through the standard installation process.
E.g. brew cask install google-chrome
Cons
Con Relatively complicated setup and installation
Installing and setting pkgsrc up is a bit more complicated than in other package managers where it often consists in running a single script.
Con Not so broadly used on MacOS as compared with MacPorts
You do not hear about Pkgsrc as openly as you hear the words "HomeBrew" or "MacPorts".
Con Outdated packages
Some packages are outdated.
Con Can't install some packages
Even building well known packages (except MacPorts) from source using the ports can fail.
Con Cask update is usually manual
This defeats the purpose of the packet manager.
Con Requires Xcode
Homebrew Cask requires that Xcode is installed, which may be more work than what some want to spend on configuring this app.
Con Software no longer needed by anything (orphans) is hard to delete
Con The developers are hostile to the users reporting issues
Con Silently spies on the user by default
See here.
Con Duplicate apps found in brew may cause issue
There are warnings provided that apps found in brew should not be installed with brew cask (and vice versa). While the user is warned of this, mistakes can happen, which would be better to just see them avoided all together by not supplying duplicate apps.