diff --git a/USAGE.md b/USAGE.md
index 435ad3ac4..0841a9737 100644
--- a/USAGE.md
+++ b/USAGE.md
@@ -21,6 +21,8 @@
   * [Understanding how to respond to new violations](#understanding-how-to-respond-to-new-violations)
 * [Recording existing violations](#recording-existing-violations)
   * [Understanding the package todo file](#understanding-the-package-todo-file)
+  * [Understanding the list of deprecated references](#understanding-the-list-of-deprecated-references)
+* [Loading extensions](#loading-extensions)
 
 ## What problem does Packwerk solve?
 
@@ -275,3 +277,16 @@ Above is an example of a constant violation entry in `package_todo.yml`.
 * `components/merchant/app/public/merchant/generate_order.rb` - path to the file containing the violated constant
 
 Violations exist within the package that makes a violating reference. This means privacy violations of your package can be found listed in `package_todo.yml` files in the packages with the reference to a private constant.
+
+# Loading Extensions
+
+You can optionally specify ruby files that you'd like to be loaded with `packwerk` by specifying a `require` directive in `packwerk.yml`:
+```yml
+require:
+  - ./path/to/file.rb
+  - my_gem
+```
+
+`packwerk` will directly call `require` with these paths.
+You can prefix local files with a dot to define them relative to `packwerk.yml`, or you can use absolute paths.
+You can also reference the name of a gem.
diff --git a/lib/packwerk.rb b/lib/packwerk.rb
index 9da66f7d8..4f2a9994c 100644
--- a/lib/packwerk.rb
+++ b/lib/packwerk.rb
@@ -22,6 +22,7 @@ module Packwerk
   autoload :ConstantNameInspector
   autoload :ConstNodeInspector
   autoload :PackageTodo
+  autoload :ExtensionLoader
   autoload :FileProcessor
   autoload :FilesForProcessing
   autoload :Graph
diff --git a/lib/packwerk/configuration.rb b/lib/packwerk/configuration.rb
index 4b13f1e0d..d921250a3 100644
--- a/lib/packwerk/configuration.rb
+++ b/lib/packwerk/configuration.rb
@@ -49,6 +49,12 @@ def initialize(configs = {}, config_path: nil)
       @cache_directory = Pathname.new(configs["cache_directory"] || "tmp/cache/packwerk")
       @config_path = config_path
 
+      if configs.key?("require")
+        configs["require"].each do |require_directive|
+          ExtensionLoader.load(require_directive, @root_path)
+        end
+      end
+
       if configs["load_paths"]
         warning = <<~WARNING
           DEPRECATION WARNING: The 'load_paths' key in `packwerk.yml` is deprecated.
diff --git a/lib/packwerk/extension_loader.rb b/lib/packwerk/extension_loader.rb
new file mode 100644
index 000000000..e7e99d3fc
--- /dev/null
+++ b/lib/packwerk/extension_loader.rb
@@ -0,0 +1,24 @@
+# typed: strict
+# frozen_string_literal: true
+
+module Packwerk
+  # This class handles loading extensions to packwerk using the `require` directive
+  # in the `packwerk.yml` configuration.
+  class ExtensionLoader
+    class << self
+      extend T::Sig
+      sig { params(require_directive: String, config_dir_path: String).void }
+      def load(require_directive, config_dir_path)
+        # We want to transform the require directive to behave differently
+        # if it's a specific local file being required versus a gem
+        if require_directive.start_with?(".")
+          require File.join(config_dir_path, require_directive)
+        else
+          require require_directive
+        end
+      end
+    end
+  end
+
+  private_constant :ExtensionLoader
+end
diff --git a/test/fixtures/skeleton/config/my_extension.rb b/test/fixtures/skeleton/config/my_extension.rb
new file mode 100644
index 000000000..6ff1c10c3
--- /dev/null
+++ b/test/fixtures/skeleton/config/my_extension.rb
@@ -0,0 +1,2 @@
+module MySpecialExtension
+end
diff --git a/test/fixtures/skeleton/packwerk.yml b/test/fixtures/skeleton/packwerk.yml
index 573a73e3b..7cea52813 100644
--- a/test/fixtures/skeleton/packwerk.yml
+++ b/test/fixtures/skeleton/packwerk.yml
@@ -4,3 +4,6 @@ include:
 exclude:
   - "**/temp.rb"
 parallel: false
+require:
+  - ./config/my_extension.rb
+  - pathname
diff --git a/test/integration/custom_executable_test.rb b/test/integration/custom_executable_test.rb
index e0d569ec1..9b7cf681a 100644
--- a/test/integration/custom_executable_test.rb
+++ b/test/integration/custom_executable_test.rb
@@ -80,8 +80,8 @@ class CustomExecutableTest < Minitest::Test
 
         package_todo_content_after_update = read_package_todo
         expected_output = <<~EOS
-          📦 Packwerk is inspecting 13 files
-          \\.\\.\\.\\.\\.\\.\\.\\.\\.\\.\\.\\.\\.
+          📦 Packwerk is inspecting 14 files
+          \\.\\.\\.\\.\\.\\.\\.\\.\\.\\.\\.\\.\\.\\.
           📦 Finished in \\d+\\.\\d+ seconds
 
           No offenses detected
@@ -115,8 +115,8 @@ class CustomExecutableTest < Minitest::Test
           package_todo_content_after_update =
             read_package_todo.reject { |k, _v| k.match?(timeline_package_todo_path) }
           expected_output = <<~EOS
-            📦 Packwerk is inspecting 14 files
-            \\.\\.\\.\\.\\.\\.\\.\\.\\.\\.\\.\\.\\.\\.
+            📦 Packwerk is inspecting 15 files
+            \\.\\.\\.\\.\\.\\.\\.\\.\\.\\.\\.\\.\\.\\.\\.
             📦 Finished in \\d+\\.\\d+ seconds
 
             No offenses detected