diff --git a/Library/Homebrew/vendor/bundle/bundler/setup.rb b/Library/Homebrew/vendor/bundle/bundler/setup.rb
index 8cb674989f..7bb740ad51 100644
--- a/Library/Homebrew/vendor/bundle/bundler/setup.rb
+++ b/Library/Homebrew/vendor/bundle/bundler/setup.rb
@@ -7,7 +7,7 @@ $:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/gems/concurrent-ruby-1.1.9
 $:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/gems/i18n-1.8.11/lib"
 $:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/gems/minitest-5.15.0/lib"
 $:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/gems/tzinfo-2.0.4/lib"
-$:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/gems/zeitwerk-2.5.2/lib"
+$:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/gems/zeitwerk-2.5.3/lib"
 $:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/gems/activesupport-6.1.4.3/lib"
 $:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/gems/public_suffix-4.0.6/lib"
 $:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/gems/addressable-2.8.0/lib"
diff --git a/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk.rb b/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk.rb
similarity index 100%
rename from Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk.rb
rename to Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk.rb
diff --git a/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk/error.rb b/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk/error.rb
similarity index 100%
rename from Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk/error.rb
rename to Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk/error.rb
diff --git a/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk/explicit_namespace.rb b/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk/explicit_namespace.rb
similarity index 100%
rename from Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk/explicit_namespace.rb
rename to Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk/explicit_namespace.rb
diff --git a/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk/gem_inflector.rb b/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk/gem_inflector.rb
similarity index 100%
rename from Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk/gem_inflector.rb
rename to Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk/gem_inflector.rb
diff --git a/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk/inflector.rb b/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk/inflector.rb
similarity index 100%
rename from Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk/inflector.rb
rename to Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk/inflector.rb
diff --git a/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk/kernel.rb b/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk/kernel.rb
similarity index 98%
rename from Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk/kernel.rb
rename to Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk/kernel.rb
index 1fed5a1acf..875381e6f3 100644
--- a/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk/kernel.rb
+++ b/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk/kernel.rb
@@ -29,7 +29,6 @@ module Kernel
         required
       else
         loader.on_dir_autoloaded(path)
-        $LOADED_FEATURES << path
         true
       end
     else
diff --git a/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk/loader.rb b/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk/loader.rb
similarity index 96%
rename from Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk/loader.rb
rename to Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk/loader.rb
index a0b96210e5..c99ad17718 100644
--- a/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk/loader.rb
+++ b/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk/loader.rb
@@ -123,7 +123,13 @@ module Zeitwerk
     # @sig () -> void
     def unload
       mutex.synchronize do
-        abspaths_of_unloaded_crefs = Set.new
+        # We are going to keep track of the files that were required by our
+        # autoloads to later remove them from $LOADED_FEATURES, thus making them
+        # loadable by Kernel#require again.
+        #
+        # Directories are not stored in $LOADED_FEATURES, keeping track of files
+        # is enough.
+        unloaded_files = Set.new
 
         autoloads.each do |abspath, (parent, cname)|
           if parent.autoload?(cname)
@@ -133,7 +139,7 @@ module Zeitwerk
             # and the constant path would escape unloadable_cpath? This is just
             # defensive code to clean things up as much as we are able to.
             unload_cref(parent, cname)
-            abspaths_of_unloaded_crefs.add(abspath)
+            unloaded_files.add(abspath) if ruby?(abspath)
           end
         end
 
@@ -144,14 +150,10 @@ module Zeitwerk
           end
 
           unload_cref(parent, cname)
-          abspaths_of_unloaded_crefs.add(abspath)
+          unloaded_files.add(abspath) if ruby?(abspath)
         end
 
-        unless abspaths_of_unloaded_crefs.empty?
-          # We remove these abspaths from $LOADED_FEATURES because, otherwise,
-          # `require`'s idempotence would prevent newly defined autoloads from
-          # loading them again.
-          #
+        unless unloaded_files.empty?
           # Bootsnap decorates Kernel#require to speed it up using a cache and
           # this optimization does not check if $LOADED_FEATURES has the file.
           #
@@ -163,7 +165,7 @@ module Zeitwerk
           # Rails applications may depend on bootsnap, so for unloading to work
           # in that setting it is preferable that we restrict our API choice to
           # one of those methods.
-          $LOADED_FEATURES.reject! { |file| abspaths_of_unloaded_crefs.member?(file) }
+          $LOADED_FEATURES.reject! { |file| unloaded_files.member?(file) }
         end
 
         autoloads.clear
diff --git a/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk/loader/callbacks.rb b/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk/loader/callbacks.rb
similarity index 100%
rename from Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk/loader/callbacks.rb
rename to Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk/loader/callbacks.rb
diff --git a/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk/loader/config.rb b/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk/loader/config.rb
similarity index 100%
rename from Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk/loader/config.rb
rename to Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk/loader/config.rb
diff --git a/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk/loader/helpers.rb b/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk/loader/helpers.rb
similarity index 100%
rename from Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk/loader/helpers.rb
rename to Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk/loader/helpers.rb
diff --git a/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk/real_mod_name.rb b/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk/real_mod_name.rb
similarity index 100%
rename from Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk/real_mod_name.rb
rename to Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk/real_mod_name.rb
diff --git a/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk/registry.rb b/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk/registry.rb
similarity index 100%
rename from Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk/registry.rb
rename to Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk/registry.rb
diff --git a/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk/version.rb b/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk/version.rb
similarity index 71%
rename from Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk/version.rb
rename to Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk/version.rb
index 0f8f24a444..276eded22f 100644
--- a/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.2/lib/zeitwerk/version.rb
+++ b/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/zeitwerk-2.5.3/lib/zeitwerk/version.rb
@@ -1,5 +1,5 @@
 # frozen_string_literal: true
 
 module Zeitwerk
-  VERSION = "2.5.2"
+  VERSION = "2.5.3"
 end