diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index d974882..9e15843 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -51,15 +51,3 @@ jobs:
           ruby-version: head
       - name: Run style checks
         run: bundle exec rubocop
-  documentation:
-    runs-on: ubuntu-latest
-    name: CLI Documentation
-    steps:
-      - uses: actions/checkout@8230315d06ad95c617244d2f265d237a1682d445
-      - name: Set up Ruby
-        uses: ruby/setup-ruby@eae47962baca661befdfd24e4d6c34ade04858f7
-        with:
-          bundler-cache: true
-          ruby-version: head
-      - name: Check autogenerated documentation
-        run: ruby docs/verify_docs.rb
diff --git a/Gemfile.lock b/Gemfile.lock
index c68344c..39a2cd3 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -17,12 +17,12 @@ GIT
 PATH
   remote: .
   specs:
-    packs (0.0.24)
+    packs (0.0.25)
       code_ownership (>= 1.33.0)
-      colorize
       packs-specification
       packwerk
       parse_packwerk
+      rainbow
       rubocop-packs
       sorbet-runtime
       thor
@@ -61,7 +61,6 @@ GEM
     code_teams (1.0.2)
       sorbet-runtime
     coderay (1.1.3)
-    colorize (1.1.0)
     concurrent-ruby (1.2.2)
     constant_resolver (0.2.0)
     crass (1.0.6)
@@ -81,10 +80,10 @@ GEM
     nokogiri (1.15.3)
       mini_portile2 (~> 2.8.2)
       racc (~> 1.4)
-    packs-specification (0.0.9)
+    packs-specification (0.0.10)
       sorbet-runtime
     parallel (1.23.0)
-    parse_packwerk (0.19.3)
+    parse_packwerk (0.20.0)
       sorbet-runtime
     parser (3.2.2.3)
       ast (~> 2.4.1)
@@ -145,21 +144,19 @@ GEM
       rubocop (~> 1.41)
     rubocop-factory_bot (2.23.1)
       rubocop (~> 1.33)
-    rubocop-packs (0.0.42)
+    rubocop-packs (0.0.43)
       activesupport
       packs-specification
       parse_packwerk
-      rubocop
+      rubocop (~> 1.0)
       rubocop-sorbet
       sorbet-runtime
     rubocop-rspec (2.23.2)
       rubocop (~> 1.33)
       rubocop-capybara (~> 2.17)
       rubocop-factory_bot (~> 2.22)
-    rubocop-sorbet (0.7.2)
+    rubocop-sorbet (0.7.3)
       rubocop (>= 0.90.0)
-    ruby-graphviz (1.2.5)
-      rexml
     ruby-progressbar (1.13.0)
     smart_properties (1.17.0)
     sorbet (0.5.10957)
@@ -208,12 +205,9 @@ GEM
     unparser (0.6.8)
       diff-lcs (~> 1.3)
       parser (>= 3.2.0)
-    visualize_packs (0.3.1)
-      code_ownership
+    visualize_packs (0.5.3)
       packs-specification
-      parse_packwerk
-      rake
-      ruby-graphviz
+      parse_packwerk (>= 0.20.0)
       sorbet-runtime
     wisper (2.0.1)
     yard (0.9.34)
diff --git a/docs/verify_docs.rb b/docs/verify_docs.rb
deleted file mode 100644
index 9c205e6..0000000
--- a/docs/verify_docs.rb
+++ /dev/null
@@ -1,41 +0,0 @@
-# typed: strict
-
-require 'bundler/inline'
-
-# Send is to ward off Sorbet which can't type this method invocation
-send(:gemfile) do
-  send(:source, 'https://rubygems.org')
-  gem 'packs', path: '../'
-end
-
-all_docs = []
-Packs::CLI.all_commands.each do |_command_name, command|
-  all_docs << <<~DOCUMENTATION
-    ## #{command.description}
-    `bin/packs #{command.usage}`
-
-  DOCUMENTATION
-
-  if command.long_description
-    all_docs << command.long_description
-    all_docs << "\n"
-  end
-end
-
-new_autogenerated_content = <<~MARKDOWN.chomp
-  ## CLI Documentation
-  #{all_docs.join}
-  ## Releasing
-MARKDOWN
-
-readme = Pathname.new('README.md')
-new_content = readme.read.gsub(/## CLI Documentation.*?## Releasing/m, new_autogenerated_content)
-
-if ENV['OVERWRITE']
-  readme.write(new_content)
-elsif readme.read == new_content
-  exit 0
-else
-  puts 'README.md is out of date. Use OVERWRITE=1 ruby docs/verify_docs.rb'
-  exit 1
-end
diff --git a/lib/packs.rb b/lib/packs.rb
index 2de84b5..154b686 100644
--- a/lib/packs.rb
+++ b/lib/packs.rb
@@ -4,7 +4,7 @@
 require 'fileutils'
 
 # External gem requires
-require 'colorized_string'
+require 'rainbow'
 
 # Internal gem requires
 require 'packs-specification'
diff --git a/lib/packs/logging.rb b/lib/packs/logging.rb
index 5b8b526..15be4d1 100644
--- a/lib/packs/logging.rb
+++ b/lib/packs/logging.rb
@@ -1,6 +1,6 @@
 # typed: strict
 
-require 'colorized_string'
+require 'rainbow'
 
 module Packs
   module Logging
@@ -9,14 +9,14 @@ module Logging
     sig { params(title: String, block: T.proc.void).void }
     def self.section(title, &block)
       print_divider
-      out ColorizedString.new(title).green.bold
+      out Rainbow(title).green.bold
       out "\n"
       yield
     end
 
     sig { params(text: String).void }
     def self.print_bold_green(text)
-      out ColorizedString.new(text).green.bold
+      out Rainbow(text).green.bold
     end
 
     sig { params(text: String).void }
diff --git a/lib/packs/private.rb b/lib/packs/private.rb
index 49ebefa..919b3f0 100644
--- a/lib/packs/private.rb
+++ b/lib/packs/private.rb
@@ -2,7 +2,7 @@
 
 require 'pathname'
 require 'fileutils'
-require 'colorized_string'
+require 'rainbow'
 require 'sorbet-runtime'
 
 require 'packs/private/file_move_operation'
@@ -313,7 +313,7 @@ def self.package_filepath(file_move_operation, per_file_processors)
     sig { params(origin: Pathname, destination: Pathname).void }
     def self.idempotent_mv(origin, destination)
       if origin.exist? && destination.exist?
-        Logging.print ColorizedString.new("[SKIP] Not moving #{origin}, #{destination} already exists").red
+        Logging.print Rainbow("[SKIP] Not moving #{origin}, #{destination} already exists").red
       elsif origin.exist? && !destination.exist?
         destination.dirname.mkpath
 
@@ -321,11 +321,11 @@ def self.idempotent_mv(origin, destination)
         # use git mv so that git knows that it was a move
         FileUtils.mv(origin, destination)
       elsif !origin.exist? && destination.exist?
-        Logging.print ColorizedString.new("[SKIP] Not moving #{origin}, does not exist, (#{destination} already exists)").red
+        Logging.print Rainbow("[SKIP] Not moving #{origin}, does not exist, (#{destination} already exists)").red
       else
         # We could choose to print this in a `--verbose` mode. For now, we find that printing this text in red confuses folks more than it informs them.
         # This is because it's perfectly common for a spec to not exist for a file, so at best it's a warning.
-        # Logging.print ColorizedString.new("[SKIP] Not moving #{origin}, does not exist").red
+        # Logging.print Rainbow("[SKIP] Not moving #{origin}, does not exist").red
       end
     end
 
diff --git a/packs.gemspec b/packs.gemspec
index 6708d21..86c19cd 100644
--- a/packs.gemspec
+++ b/packs.gemspec
@@ -1,6 +1,6 @@
 Gem::Specification.new do |spec|
   spec.name          = 'packs'
-  spec.version       = '0.0.24'
+  spec.version       = '0.0.25'
   spec.authors       = ['Gusto Engineers']
   spec.email         = ['dev@gusto.com']
 
@@ -29,10 +29,10 @@ Gem::Specification.new do |spec|
   spec.executables = %w[packs]
 
   spec.add_dependency 'code_ownership', '>= 1.33.0'
-  spec.add_dependency 'colorize'
   spec.add_dependency 'packs-specification'
   spec.add_dependency 'packwerk'
   spec.add_dependency 'parse_packwerk'
+  spec.add_dependency 'rainbow'
   spec.add_dependency 'rubocop-packs'
   spec.add_dependency 'sorbet-runtime'
   spec.add_dependency 'thor'
diff --git a/sorbet/rbi/gems/colorize@0.8.1.rbi b/sorbet/rbi/gems/colorize@0.8.1.rbi
deleted file mode 100644
index ef5d54e..0000000
--- a/sorbet/rbi/gems/colorize@0.8.1.rbi
+++ /dev/null
@@ -1,84 +0,0 @@
-# DO NOT EDIT MANUALLY
-# This is an autogenerated file for types exported from the `colorize` gem.
-# Please instead update this file by running `bin/tapioca gem colorize`.
-
-# typed: true
-
-module Colorize; end
-
-module Colorize::ClassMethods
-  def color_codes; end
-  def color_matrix(_ = T.unsafe(nil)); end
-  def color_methods; end
-  def color_samples; end
-  def colors; end
-  def disable_colorization(value = T.unsafe(nil)); end
-  def disable_colorization=(value); end
-  def mode_codes; end
-  def modes; end
-  def modes_methods; end
-end
-
-module Colorize::InstanceMethods
-  def colorize(params); end
-  def colorized?; end
-  def uncolorize; end
-
-  private
-
-  def background_color(color); end
-  def color(color); end
-  def color_from_symbol(match, symbol); end
-  def colors_from_hash(match, hash); end
-  def colors_from_params(match, params); end
-  def defaults_colors(match); end
-  def mode(mode); end
-  def require_windows_libs; end
-  def scan_for_colors; end
-  def split_colors(match); end
-end
-
-class ColorizedString < ::String
-  def black; end
-  def blink; end
-  def blue; end
-  def bold; end
-  def cyan; end
-  def green; end
-  def hide; end
-  def italic; end
-  def light_black; end
-  def light_blue; end
-  def light_cyan; end
-  def light_green; end
-  def light_magenta; end
-  def light_red; end
-  def light_white; end
-  def light_yellow; end
-  def magenta; end
-  def on_black; end
-  def on_blue; end
-  def on_cyan; end
-  def on_green; end
-  def on_light_black; end
-  def on_light_blue; end
-  def on_light_cyan; end
-  def on_light_green; end
-  def on_light_magenta; end
-  def on_light_red; end
-  def on_light_white; end
-  def on_light_yellow; end
-  def on_magenta; end
-  def on_red; end
-  def on_white; end
-  def on_yellow; end
-  def red; end
-  def swap; end
-  def underline; end
-  def white; end
-  def yellow; end
-
-  class << self
-    def [](string); end
-  end
-end
diff --git a/sorbet/rbi/gems/rainbow@3.1.1.rbi b/sorbet/rbi/gems/rainbow@3.1.1.rbi
index e704587..a1a4eb4 100644
--- a/sorbet/rbi/gems/rainbow@3.1.1.rbi
+++ b/sorbet/rbi/gems/rainbow@3.1.1.rbi
@@ -4,154 +4,401 @@
 # This is an autogenerated file for types exported from the `rainbow` gem.
 # Please instead update this file by running `bin/tapioca gem rainbow`.
 
+class Object < ::BasicObject
+  include ::Kernel
+  include ::ActiveSupport::ForkTracker::CoreExt
+  include ::ActiveSupport::ForkTracker::CoreExtPrivate
+  include ::PP::ObjectMixin
+
+  private
+
+  # source://rainbow//lib/rainbow/global.rb#23
+  def Rainbow(string); end
+end
+
+# source://rainbow//lib/rainbow/string_utils.rb#3
 module Rainbow
   class << self
+    # source://rainbow//lib/rainbow/global.rb#10
     def enabled; end
+
+    # source://rainbow//lib/rainbow/global.rb#14
     def enabled=(value); end
+
+    # source://rainbow//lib/rainbow/global.rb#6
     def global; end
+
+    # source://rainbow//lib/rainbow.rb#6
     def new; end
+
+    # source://rainbow//lib/rainbow/global.rb#18
     def uncolor(string); end
   end
 end
 
+# source://rainbow//lib/rainbow/color.rb#4
 class Rainbow::Color
+  # Returns the value of attribute ground.
+  #
+  # source://rainbow//lib/rainbow/color.rb#5
   def ground; end
 
   class << self
+    # source://rainbow//lib/rainbow/color.rb#7
     def build(ground, values); end
+
+    # source://rainbow//lib/rainbow/color.rb#40
     def parse_hex_color(hex); end
   end
 end
 
+# source://rainbow//lib/rainbow/color.rb#54
 class Rainbow::Color::Indexed < ::Rainbow::Color
+  # @return [Indexed] a new instance of Indexed
+  #
+  # source://rainbow//lib/rainbow/color.rb#57
   def initialize(ground, num); end
 
+  # source://rainbow//lib/rainbow/color.rb#62
   def codes; end
+
+  # Returns the value of attribute num.
+  #
+  # source://rainbow//lib/rainbow/color.rb#55
   def num; end
 end
 
+# source://rainbow//lib/rainbow/color.rb#69
 class Rainbow::Color::Named < ::Rainbow::Color::Indexed
+  # @return [Named] a new instance of Named
+  #
+  # source://rainbow//lib/rainbow/color.rb#90
   def initialize(ground, name); end
 
   class << self
+    # source://rainbow//lib/rainbow/color.rb#82
     def color_names; end
+
+    # source://rainbow//lib/rainbow/color.rb#86
     def valid_names; end
   end
 end
 
+# source://rainbow//lib/rainbow/color.rb#70
 Rainbow::Color::Named::NAMES = T.let(T.unsafe(nil), Hash)
 
+# source://rainbow//lib/rainbow/color.rb#100
 class Rainbow::Color::RGB < ::Rainbow::Color::Indexed
+  # @return [RGB] a new instance of RGB
+  #
+  # source://rainbow//lib/rainbow/color.rb#107
   def initialize(ground, *values); end
 
+  # Returns the value of attribute b.
+  #
+  # source://rainbow//lib/rainbow/color.rb#101
   def b; end
+
+  # source://rainbow//lib/rainbow/color.rb#116
   def codes; end
+
+  # Returns the value of attribute g.
+  #
+  # source://rainbow//lib/rainbow/color.rb#101
   def g; end
+
+  # Returns the value of attribute r.
+  #
+  # source://rainbow//lib/rainbow/color.rb#101
   def r; end
 
   private
 
+  # source://rainbow//lib/rainbow/color.rb#122
   def code_from_rgb; end
 
   class << self
+    # source://rainbow//lib/rainbow/color.rb#103
     def to_ansi_domain(value); end
   end
 end
 
+# source://rainbow//lib/rainbow/color.rb#129
 class Rainbow::Color::X11Named < ::Rainbow::Color::RGB
   include ::Rainbow::X11ColorNames
 
+  # @return [X11Named] a new instance of X11Named
+  #
+  # source://rainbow//lib/rainbow/color.rb#140
   def initialize(ground, name); end
 
   class << self
+    # source://rainbow//lib/rainbow/color.rb#132
     def color_names; end
+
+    # source://rainbow//lib/rainbow/color.rb#136
     def valid_names; end
   end
 end
 
+# source://rainbow//lib/rainbow/null_presenter.rb#4
 class Rainbow::NullPresenter < ::String
+  # source://rainbow//lib/rainbow/null_presenter.rb#9
   def background(*_values); end
+
+  # source://rainbow//lib/rainbow/null_presenter.rb#9
   def bg(*_values); end
+
+  # source://rainbow//lib/rainbow/null_presenter.rb#49
   def black; end
+
+  # source://rainbow//lib/rainbow/null_presenter.rb#33
   def blink; end
+
+  # source://rainbow//lib/rainbow/null_presenter.rb#65
   def blue; end
+
+  # source://rainbow//lib/rainbow/null_presenter.rb#17
   def bold; end
+
+  # source://rainbow//lib/rainbow/null_presenter.rb#17
   def bright; end
+
+  # source://rainbow//lib/rainbow/null_presenter.rb#5
   def color(*_values); end
+
+  # source://rainbow//lib/rainbow/null_presenter.rb#45
   def cross_out; end
+
+  # source://rainbow//lib/rainbow/null_presenter.rb#73
   def cyan; end
+
+  # source://rainbow//lib/rainbow/null_presenter.rb#21
   def dark; end
+
+  # source://rainbow//lib/rainbow/null_presenter.rb#21
   def faint; end
+
+  # source://rainbow//lib/rainbow/null_presenter.rb#5
   def fg(*_values); end
+
+  # source://rainbow//lib/rainbow/null_presenter.rb#5
   def foreground(*_values); end
+
+  # source://rainbow//lib/rainbow/null_presenter.rb#57
   def green; end
+
+  # source://rainbow//lib/rainbow/null_presenter.rb#41
   def hide; end
+
+  # source://rainbow//lib/rainbow/null_presenter.rb#37
   def inverse; end
+
+  # source://rainbow//lib/rainbow/null_presenter.rb#25
   def italic; end
+
+  # source://rainbow//lib/rainbow/null_presenter.rb#69
   def magenta; end
+
+  # source://rainbow//lib/rainbow/null_presenter.rb#81
   def method_missing(method_name, *args); end
+
+  # source://rainbow//lib/rainbow/null_presenter.rb#53
   def red; end
+
+  # source://rainbow//lib/rainbow/null_presenter.rb#13
   def reset; end
+
+  # source://rainbow//lib/rainbow/null_presenter.rb#45
   def strike; end
+
+  # source://rainbow//lib/rainbow/null_presenter.rb#29
   def underline; end
+
+  # source://rainbow//lib/rainbow/null_presenter.rb#77
   def white; end
+
+  # source://rainbow//lib/rainbow/null_presenter.rb#61
   def yellow; end
 
   private
 
+  # @return [Boolean]
+  #
+  # source://rainbow//lib/rainbow/null_presenter.rb#89
   def respond_to_missing?(method_name, *args); end
 end
 
+# source://rainbow//lib/rainbow/presenter.rb#8
 class Rainbow::Presenter < ::String
+  # Sets background color of this text.
+  #
+  # source://rainbow//lib/rainbow/presenter.rb#30
   def background(*values); end
+
+  # Sets background color of this text.
+  #
+  # source://rainbow//lib/rainbow/presenter.rb#30
   def bg(*values); end
+
+  # source://rainbow//lib/rainbow/presenter.rb#92
   def black; end
+
+  # Turns on blinking attribute for this text (not well supported by terminal
+  # emulators).
+  #
+  # source://rainbow//lib/rainbow/presenter.rb#72
   def blink; end
+
+  # source://rainbow//lib/rainbow/presenter.rb#108
   def blue; end
+
+  # Turns on bright/bold for this text.
+  #
+  # source://rainbow//lib/rainbow/presenter.rb#45
   def bold; end
+
+  # Turns on bright/bold for this text.
+  #
+  # source://rainbow//lib/rainbow/presenter.rb#45
   def bright; end
+
+  # Sets color of this text.
+  #
+  # source://rainbow//lib/rainbow/presenter.rb#22
   def color(*values); end
+
+  # source://rainbow//lib/rainbow/presenter.rb#86
   def cross_out; end
+
+  # source://rainbow//lib/rainbow/presenter.rb#116
   def cyan; end
+
+  # Turns on faint/dark for this text (not well supported by terminal
+  # emulators).
+  #
+  # source://rainbow//lib/rainbow/presenter.rb#53
   def dark; end
+
+  # Turns on faint/dark for this text (not well supported by terminal
+  # emulators).
+  #
+  # source://rainbow//lib/rainbow/presenter.rb#53
   def faint; end
+
+  # Sets color of this text.
+  #
+  # source://rainbow//lib/rainbow/presenter.rb#22
   def fg(*values); end
+
+  # Sets color of this text.
+  #
+  # source://rainbow//lib/rainbow/presenter.rb#22
   def foreground(*values); end
+
+  # source://rainbow//lib/rainbow/presenter.rb#100
   def green; end
+
+  # Hides this text (set its color to the same as background).
+  #
+  # source://rainbow//lib/rainbow/presenter.rb#82
   def hide; end
+
+  # Inverses current foreground/background colors.
+  #
+  # source://rainbow//lib/rainbow/presenter.rb#77
   def inverse; end
+
+  # Turns on italic style for this text (not well supported by terminal
+  # emulators).
+  #
+  # source://rainbow//lib/rainbow/presenter.rb#61
   def italic; end
+
+  # source://rainbow//lib/rainbow/presenter.rb#112
   def magenta; end
+
+  # We take care of X11 color method call here.
+  # Such as #aqua, #ghostwhite.
+  #
+  # source://rainbow//lib/rainbow/presenter.rb#126
   def method_missing(method_name, *args); end
+
+  # source://rainbow//lib/rainbow/presenter.rb#96
   def red; end
+
+  # Resets terminal to default colors/backgrounds.
+  #
+  # It shouldn't be needed to use this method because all methods
+  # append terminal reset code to end of string.
+  #
+  # source://rainbow//lib/rainbow/presenter.rb#40
   def reset; end
+
+  # source://rainbow//lib/rainbow/presenter.rb#86
   def strike; end
+
+  # Turns on underline decoration for this text.
+  #
+  # source://rainbow//lib/rainbow/presenter.rb#66
   def underline; end
+
+  # source://rainbow//lib/rainbow/presenter.rb#120
   def white; end
+
+  # source://rainbow//lib/rainbow/presenter.rb#104
   def yellow; end
 
   private
 
+  # @return [Boolean]
+  #
+  # source://rainbow//lib/rainbow/presenter.rb#134
   def respond_to_missing?(method_name, *args); end
+
+  # source://rainbow//lib/rainbow/presenter.rb#140
   def wrap_with_sgr(codes); end
 end
 
+# source://rainbow//lib/rainbow/presenter.rb#9
 Rainbow::Presenter::TERM_EFFECTS = T.let(T.unsafe(nil), Hash)
 
+# source://rainbow//lib/rainbow/string_utils.rb#4
 class Rainbow::StringUtils
   class << self
+    # source://rainbow//lib/rainbow/string_utils.rb#17
     def uncolor(string); end
+
+    # source://rainbow//lib/rainbow/string_utils.rb#5
     def wrap_with_sgr(string, codes); end
   end
 end
 
+# source://rainbow//lib/rainbow/wrapper.rb#7
 class Rainbow::Wrapper
+  # @return [Wrapper] a new instance of Wrapper
+  #
+  # source://rainbow//lib/rainbow/wrapper.rb#10
   def initialize(enabled = T.unsafe(nil)); end
 
+  # Returns the value of attribute enabled.
+  #
+  # source://rainbow//lib/rainbow/wrapper.rb#8
   def enabled; end
+
+  # Sets the attribute enabled
+  #
+  # @param value the value to set the attribute enabled to.
+  #
+  # source://rainbow//lib/rainbow/wrapper.rb#8
   def enabled=(_arg0); end
+
+  # source://rainbow//lib/rainbow/wrapper.rb#14
   def wrap(string); end
 end
 
+# source://rainbow//lib/rainbow/x11_color_names.rb#4
 module Rainbow::X11ColorNames; end
+
+# source://rainbow//lib/rainbow/x11_color_names.rb#5
 Rainbow::X11ColorNames::NAMES = T.let(T.unsafe(nil), Hash)
diff --git a/spec/packs_spec.rb b/spec/packs_spec.rb
index 79568a6..7c0e2fe 100644
--- a/spec/packs_spec.rb
+++ b/spec/packs_spec.rb
@@ -1095,12 +1095,12 @@ def write_codeownership_config
       logged_output = ''
 
       expect(Packs::Logging).to receive(:out).at_least(:once) do |string|
-        logged_output += ColorizedString.new(string).uncolorize
+        logged_output += Rainbow.uncolor(string)
         logged_output += "\n"
       end
 
       expect(Packs::Logging).to receive(:print).at_least(:once) do |string|
-        logged_output += ColorizedString.new(string).uncolorize
+        logged_output += Rainbow.uncolor(string)
         logged_output += "\n"
       end
 
diff --git a/spec/spec_helper.rb b/spec/spec_helper.rb
index 5e4f2c3..f99b58a 100644
--- a/spec/spec_helper.rb
+++ b/spec/spec_helper.rb
@@ -2,6 +2,8 @@
 # frozen_string_literal: true
 
 require 'packs'
+# This require should eventually be done in packs/rspec/support, since it's needed to load the Dir.mktmpdir method
+require 'tmpdir'
 require 'packs/rspec/support'
 
 RSpec.configure do |config|
diff --git a/spec/verify_docs_spec.rb b/spec/verify_docs_spec.rb
new file mode 100644
index 0000000..e9172c7
--- /dev/null
+++ b/spec/verify_docs_spec.rb
@@ -0,0 +1,44 @@
+# typed: false
+
+RSpec.describe Packs, :skip_chdir_to_tmpdir do
+  let(:readme) do
+    Pathname.new('README.md')
+  end
+
+  let(:actual_content) { readme.read }
+
+  let(:expected_content) do
+    all_docs = []
+    Packs::CLI.all_commands.each do |_command_name, command|
+      all_docs << <<~DOCUMENTATION
+        ## #{command.description}
+        `bin/packs #{command.usage}`
+
+      DOCUMENTATION
+
+      if command.long_description
+        all_docs << command.long_description
+        all_docs << "\n"
+      end
+    end
+
+    new_autogenerated_content = <<~MARKDOWN.chomp
+      ## CLI Documentation
+      #{all_docs.join}
+      ## Releasing
+    MARKDOWN
+    new_content = readme.read.gsub(/## CLI Documentation.*?## Releasing/m, new_autogenerated_content)
+
+    new_content
+  end
+
+  describe 'CLI Documentation' do
+    it 'is up to date' do
+      if ENV['OVERWRITE']
+        readme.write(expected_content)
+      else
+        expect(actual_content).to eq(expected_content), 'README.md is out of date. Use OVERWRITE=1 bundle exec rspec'
+      end
+    end
+  end
+end