diff --git a/Gemfile b/Gemfile
index c59ccbe1a..15a2a60d9 100644
--- a/Gemfile
+++ b/Gemfile
@@ -7,3 +7,7 @@ gem "rake-compiler"
 gem "test-unit", "~> 3.0"
 gem "test-unit-rr"
 gem "json-schema"
+
+group :development do
+  gem "zeitwerk", git: "https://github.com/paracycle/zeitwerk.git", branch: "uk-add-syntax-tree-inflector"
+end
diff --git a/lib/debug/open.rb b/lib/debug/open.rb
index ceb41d052..f5d689aef 100644
--- a/lib/debug/open.rb
+++ b/lib/debug/open.rb
@@ -7,6 +7,21 @@
 # Otherwise, UNIX domain socket is used.
 #
 
+require "zeitwerk"
+
+loader = Zeitwerk::Loader.for_gem(warn_on_extra_files: false)
+loader.ignore(
+  "lib/debug/start.rb",
+  "lib/debug/open.rb",
+  "lib/debug/open_nonstop.rb",
+  "lib/debug/prelude.rb",
+  "lib/debug/dap_custom/traceInspector.rb"
+)
+loader.enable_reloading
+loader.setup
+loader.log!
+puts "Zeitwerk configured!"
+
 require_relative 'session'
 return unless defined?(DEBUGGER__)