diff --git a/resources/files/operating_system.rb b/resources/files/operating_system.rb
index d75f0d8af..bcf583012 100644
--- a/resources/files/operating_system.rb
+++ b/resources/files/operating_system.rb
@@ -38,7 +38,7 @@ def operating_system_defaults
 
   RubyInstaller::Runtime.enable_msys_apps(for_gem_install: true) unless gem_installer.spec.extensions.empty?
 
-  if !gem_installer.options || !gem_installer.options[:ignore_dependencies] || gem_installer.options[:bundler_expected_checksum]
+  if !gem_installer.options || !gem_installer.options[:ignore_dependencies] || gem_installer.class.to_s.include?("Bundler")
     [['msys2_dependencies'      , :install_packages      ],
      ['msys2_mingw_dependencies', :install_mingw_packages]].each do |metakey, func|
 
diff --git a/test/helper/testgem/Gemfile b/test/helper/testgem/Gemfile
new file mode 100644
index 000000000..8033850c2
--- /dev/null
+++ b/test/helper/testgem/Gemfile
@@ -0,0 +1,2 @@
+source "https://dummy-url.nonexit"
+gem "testgem", "1.0.0"
diff --git a/test/test_gem_install.rb b/test/test_gem_install.rb
index 141a67dfa..d6b29d534 100644
--- a/test/test_gem_install.rb
+++ b/test/test_gem_install.rb
@@ -3,12 +3,12 @@
 
 class TestGemInstall < Minitest::Test
   # Remove installed packages per:
-  #   pacman -R mingw-w64-ucrt-x86_64-libmowgli mingw-w64-ucrt-x86_64-libguess ed
+  #   pacman -R %MINGW_PACKAGE_PREFIX%-libmowgli %MINGW_PACKAGE_PREFIX%-libguess ed
   def test_gem_install
     res = system <<-EOT.gsub("\n", "&")
-cd test/helper/testgem
-gem build testgem.gemspec
-gem install testgem-1.0.0.gem --verbose
+      cd test/helper/testgem
+      gem build testgem.gemspec
+      gem install testgem-1.0.0.gem --verbose
     EOT
     assert res, "shell commands should succeed"
 
@@ -27,6 +27,23 @@ def test_gem_install
     FileUtils.rm("test/helper/testgem/testgem-1.0.0.gem")
   end
 
+  def test_bundle_install
+    remove_pacman_packages_for_test
+    FileUtils.mkdir_p "test/helper/testgem/vendor/cache"
+    res = system <<-EOT.gsub("\n", "&")
+      cd test/helper/testgem
+      gem build testgem.gemspec
+      copy /b testgem-1.0.0.gem "vendor/cache/"
+      bundle install --local
+    EOT
+    assert res, "shell commands should succeed"
+
+    out = IO.popen("bundle exec ruby -rtestgem -e \"puts Libguess.determine_encoding('abc', 'Greek')\"", chdir: "test/helper/testgem", &:read)
+    assert_match(/UTF-8/, out.scrub, "call the ruby API of the testgem")
+
+    assert system("gem uninstall testgem --executables --force"), "uninstall testgem"
+  end
+
   if RUBY_VERSION < "3.0"
     TESTUSER = "ritestuser"
   else
@@ -64,6 +81,13 @@ def with_test_user(testname: nil)
     end
   end
 
+  private def remove_pacman_packages_for_test
+    RubyInstaller::Runtime.msys2_installation.with_msys_apps_enabled do
+      system("pacman -R --noconfirm %MINGW_PACKAGE_PREFIX%-libmowgli %MINGW_PACKAGE_PREFIX%-libguess ed")
+    end
+  end
+
+
   def test_user_gem_install
     unless ENV['USERNAME'] == TESTUSER
       RubyInstaller::Runtime.msys2_installation.with_msys_apps_enabled do
@@ -74,9 +98,7 @@ def test_user_gem_install
       test_gem_install
     end
     unless ENV['USERNAME'] == TESTUSER
-      RubyInstaller::Runtime.msys2_installation.with_msys_apps_enabled do
-        system("pacman -R --noconfirm %MINGW_PACKAGE_PREFIX%-libmowgli %MINGW_PACKAGE_PREFIX%-libguess ed")
-      end
+      remove_pacman_packages_for_test
     end
   end