diff --git a/spec/bundler/spec_helper.rb b/spec/bundler/spec_helper.rb
index 96cd7be472..f0d6bce006 100644
--- a/spec/bundler/spec_helper.rb
+++ b/spec/bundler/spec_helper.rb
@@ -38,6 +38,7 @@ require_relative "support/indexes"
 require_relative "support/matchers"
 require_relative "support/permissions"
 require_relative "support/platforms"
+require_relative "support/windows_tag_group"
 
 $debug = false
 
@@ -56,6 +57,7 @@ RSpec.configure do |config|
   config.include Spec::Path
   config.include Spec::Platforms
   config.include Spec::Permissions
+  config.include Spec::WindowsTagGroup
 
   # Enable flags like --only-failures and --next-failure
   config.example_status_persistence_file_path = ".rspec_status"
@@ -129,4 +131,12 @@ RSpec.configure do |config|
   ensure
     reset!
   end
+
+  Spec::WindowsTagGroup::EXAMPLE_MAPPINGS.each do |tag, file_paths|
+    file_pattern = Regexp.union(file_paths.map {|path| Regexp.new(Regexp.escape(path) + "$") })
+
+    config.define_derived_metadata(file_path: file_pattern) do |metadata|
+      metadata[tag] = true
+    end
+  end
 end
diff --git a/spec/bundler/support/windows_tag_group.rb b/spec/bundler/support/windows_tag_group.rb
new file mode 100644
index 0000000000..77112a2c6c
--- /dev/null
+++ b/spec/bundler/support/windows_tag_group.rb
@@ -0,0 +1,185 @@
+# frozen_string_literal: true
+
+module Spec
+  module WindowsTagGroup
+    EXAMPLE_MAPPINGS = {
+      windows_a: [
+        "spec/runtime/setup_spec.rb",
+        "spec/commands/install_spec.rb",
+        "spec/commands/add_spec.rb",
+        "spec/install/gems/compact_index_spec.rb",
+        "spec/commands/config_spec.rb",
+        "spec/commands/pristine_spec.rb",
+        "spec/install/gemfile/path_spec.rb",
+        "spec/update/git_spec.rb",
+        "spec/commands/open_spec.rb",
+        "spec/commands/remove_spec.rb",
+        "spec/commands/show_spec.rb",
+        "spec/plugins/source/example_spec.rb",
+        "spec/commands/console_spec.rb",
+        "spec/runtime/require_spec.rb",
+        "spec/runtime/env_helpers_spec.rb",
+        "spec/runtime/gem_tasks_spec.rb",
+        "spec/install/gemfile_spec.rb",
+        "spec/commands/fund_spec.rb",
+        "spec/commands/init_spec.rb",
+        "spec/bundler/ruby_dsl_spec.rb",
+        "spec/bundler/mirror_spec.rb",
+        "spec/bundler/source/git/git_proxy_spec.rb",
+        "spec/bundler/source_list_spec.rb",
+        "spec/bundler/plugin/installer_spec.rb",
+        "spec/bundler/friendly_errors_spec.rb",
+        "spec/resolver/platform_spec.rb",
+        "spec/bundler/fetcher/downloader_spec.rb",
+        "spec/update/force_spec.rb",
+        "spec/bundler/env_spec.rb",
+        "spec/install/gems/mirror_spec.rb",
+        "spec/install/failure_spec.rb",
+        "spec/bundler/yaml_serializer_spec.rb",
+        "spec/bundler/environment_preserver_spec.rb",
+        "spec/install/gemfile/install_if_spec.rb",
+        "spec/install/gems/gemfile_source_header_spec.rb",
+        "spec/bundler/fetcher/base_spec.rb",
+        "spec/bundler/rubygems_integration_spec.rb",
+        "spec/bundler/worker_spec.rb",
+        "spec/bundler/dependency_spec.rb",
+        "spec/bundler/ui_spec.rb",
+        "spec/bundler/plugin/source_list_spec.rb",
+        "spec/bundler/source/path_spec.rb",
+      ],
+      windows_b: [
+        "spec/install/gemfile/git_spec.rb",
+        "spec/install/gems/standalone_spec.rb",
+        "spec/commands/lock_spec.rb",
+        "spec/cache/gems_spec.rb",
+        "spec/other/major_deprecation_spec.rb",
+        "spec/install/gems/dependency_api_spec.rb",
+        "spec/install/gemfile/gemspec_spec.rb",
+        "spec/plugins/install_spec.rb",
+        "spec/commands/binstubs_spec.rb",
+        "spec/install/gems/flex_spec.rb",
+        "spec/runtime/inline_spec.rb",
+        "spec/commands/post_bundle_message_spec.rb",
+        "spec/runtime/executable_spec.rb",
+        "spec/lock/git_spec.rb",
+        "spec/plugins/hook_spec.rb",
+        "spec/install/allow_offline_install_spec.rb",
+        "spec/install/gems/post_install_spec.rb",
+        "spec/install/gemfile/ruby_spec.rb",
+        "spec/install/security_policy_spec.rb",
+        "spec/install/yanked_spec.rb",
+        "spec/update/gemfile_spec.rb",
+        "spec/runtime/load_spec.rb",
+        "spec/plugins/command_spec.rb",
+        "spec/commands/version_spec.rb",
+        "spec/install/prereleases_spec.rb",
+        "spec/bundler/uri_credentials_filter_spec.rb",
+        "spec/bundler/plugin_spec.rb",
+        "spec/install/gems/mirror_probe_spec.rb",
+        "spec/plugins/list_spec.rb",
+        "spec/bundler/compact_index_client/parser_spec.rb",
+        "spec/bundler/gem_version_promoter_spec.rb",
+        "spec/other/cli_dispatch_spec.rb",
+        "spec/bundler/source/rubygems_spec.rb",
+        "spec/cache/platform_spec.rb",
+        "spec/update/gems/fund_spec.rb",
+        "spec/bundler/stub_specification_spec.rb",
+        "spec/bundler/retry_spec.rb",
+        "spec/bundler/installer/spec_installation_spec.rb",
+        "spec/bundler/spec_set_spec.rb",
+        "spec/quality_es_spec.rb",
+        "spec/bundler/index_spec.rb",
+        "spec/other/cli_man_pages_spec.rb",
+      ],
+      windows_c: [
+        "spec/commands/newgem_spec.rb",
+        "spec/commands/exec_spec.rb",
+        "spec/commands/clean_spec.rb",
+        "spec/commands/platform_spec.rb",
+        "spec/cache/git_spec.rb",
+        "spec/install/gemfile/groups_spec.rb",
+        "spec/commands/cache_spec.rb",
+        "spec/commands/check_spec.rb",
+        "spec/commands/list_spec.rb",
+        "spec/install/path_spec.rb",
+        "spec/bundler/cli_spec.rb",
+        "spec/install/bundler_spec.rb",
+        "spec/install/git_spec.rb",
+        "spec/commands/doctor_spec.rb",
+        "spec/bundler/dsl_spec.rb",
+        "spec/install/gems/fund_spec.rb",
+        "spec/install/gems/env_spec.rb",
+        "spec/bundler/ruby_version_spec.rb",
+        "spec/bundler/definition_spec.rb",
+        "spec/install/gemfile/eval_gemfile_spec.rb",
+        "spec/plugins/source_spec.rb",
+        "spec/install/gems/dependency_api_fallback_spec.rb",
+        "spec/plugins/uninstall_spec.rb",
+        "spec/bundler/plugin/index_spec.rb",
+        "spec/bundler/bundler_spec.rb",
+        "spec/bundler/fetcher_spec.rb",
+        "spec/bundler/source/rubygems/remote_spec.rb",
+        "spec/bundler/lockfile_parser_spec.rb",
+        "spec/cache/cache_path_spec.rb",
+        "spec/bundler/source/git_spec.rb",
+        "spec/bundler/source_spec.rb",
+        "spec/commands/ssl_spec.rb",
+        "spec/bundler/fetcher/compact_index_spec.rb",
+        "spec/bundler/plugin/api_spec.rb",
+        "spec/bundler/endpoint_specification_spec.rb",
+        "spec/bundler/fetcher/index_spec.rb",
+        "spec/bundler/settings/validator_spec.rb",
+        "spec/bundler/build_metadata_spec.rb",
+        "spec/bundler/current_ruby_spec.rb",
+        "spec/bundler/installer/gem_installer_spec.rb",
+        "spec/bundler/cli_common_spec.rb",
+        "spec/bundler/ci_detector_spec.rb",
+      ],
+      windows_d: [
+        "spec/commands/outdated_spec.rb",
+        "spec/commands/update_spec.rb",
+        "spec/lock/lockfile_spec.rb",
+        "spec/install/deploy_spec.rb",
+        "spec/install/gemfile/sources_spec.rb",
+        "spec/runtime/self_management_spec.rb",
+        "spec/install/gemfile/specific_platform_spec.rb",
+        "spec/commands/info_spec.rb",
+        "spec/install/gems/resolving_spec.rb",
+        "spec/install/gemfile/platform_spec.rb",
+        "spec/bundler/gem_helper_spec.rb",
+        "spec/install/global_cache_spec.rb",
+        "spec/runtime/platform_spec.rb",
+        "spec/update/gems/post_install_spec.rb",
+        "spec/install/gems/native_extensions_spec.rb",
+        "spec/install/force_spec.rb",
+        "spec/cache/path_spec.rb",
+        "spec/install/gemspecs_spec.rb",
+        "spec/commands/help_spec.rb",
+        "spec/bundler/shared_helpers_spec.rb",
+        "spec/bundler/settings_spec.rb",
+        "spec/resolver/basic_spec.rb",
+        "spec/install/gemfile/force_ruby_platform_spec.rb",
+        "spec/commands/licenses_spec.rb",
+        "spec/install/gemfile/lockfile_spec.rb",
+        "spec/bundler/fetcher/dependency_spec.rb",
+        "spec/quality_spec.rb",
+        "spec/bundler/remote_specification_spec.rb",
+        "spec/install/process_lock_spec.rb",
+        "spec/install/binstubs_spec.rb",
+        "spec/bundler/compact_index_client/updater_spec.rb",
+        "spec/bundler/ui/shell_spec.rb",
+        "spec/other/ext_spec.rb",
+        "spec/commands/issue_spec.rb",
+        "spec/update/path_spec.rb",
+        "spec/bundler/plugin/api/source_spec.rb",
+        "spec/install/gems/win32_spec.rb",
+        "spec/bundler/plugin/dsl_spec.rb",
+        "spec/runtime/requiring_spec.rb",
+        "spec/bundler/plugin/events_spec.rb",
+        "spec/bundler/resolver/candidate_spec.rb",
+        "spec/bundler/digest_spec.rb",
+        "spec/bundler/fetcher/gem_remote_fetcher_spec.rb",
+      ],
+    }.freeze
+  end
+end