diff --git a/Dockerfile b/Dockerfile
index b10b783cea..dfc9ded250 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -194,7 +194,7 @@ ENV DEPENDABOT_NATIVE_HELPERS_PATH="/opt" \
 RUN bash /opt/terraform/helpers/build /opt/terraform && \
   bash /opt/python/helpers/build /opt/python && \
   bash /opt/dep/helpers/build /opt/dep && \
-  bash /opt/bundler/helpers/build /opt/bundler && \
+  mkdir -p /opt/bundler/v1 && bash /opt/bundler/helpers/v1/build /opt/bundler/v1 && \
   bash /opt/go_modules/helpers/build /opt/go_modules && \
   bash /opt/npm_and_yarn/helpers/build /opt/npm_and_yarn && \
   bash /opt/hex/helpers/build /opt/hex && \
diff --git a/bundler/helpers/v1/.bundle/config b/bundler/helpers/v1/.bundle/config
new file mode 100644
index 0000000000..04f57bd2ed
--- /dev/null
+++ b/bundler/helpers/v1/.bundle/config
@@ -0,0 +1,2 @@
+---
+BUNDLE_PATH: ".bundle"
diff --git a/bundler/helpers/v1/.gitignore b/bundler/helpers/v1/.gitignore
new file mode 100644
index 0000000000..9e978b139f
--- /dev/null
+++ b/bundler/helpers/v1/.gitignore
@@ -0,0 +1,9 @@
+/.bundle/*
+!/.bundle/config
+/.env
+/tmp
+/dependabot-*.gem
+Gemfile.lock
+spec/fixtures/projects/*/.bundle/
+!spec/fixtures/projects/**/Gemfile.lock
+!spec/fixtures/projects/**/vendor
diff --git a/bundler/helpers/v1/Gemfile b/bundler/helpers/v1/Gemfile
new file mode 100644
index 0000000000..be8d883aed
--- /dev/null
+++ b/bundler/helpers/v1/Gemfile
@@ -0,0 +1,7 @@
+# frozen_string_literal: true
+
+source "https://rubygems.org"
+
+# NOTE: This is intentionally left blank as it's currently only used to force
+# bundler to use v1 when executing native helpers by pointing the BUNDLE_GEMFILE
+# env to this Gemfile in Dependabot::Bundler::NativeHelpers
diff --git a/bundler/helpers/build b/bundler/helpers/v1/build
similarity index 55%
rename from bundler/helpers/build
rename to bundler/helpers/v1/build
index 93f89bce2c..f1bcf37774 100755
--- a/bundler/helpers/build
+++ b/bundler/helpers/v1/build
@@ -10,9 +10,15 @@ fi
 
 helpers_dir="$(dirname "${BASH_SOURCE[0]}")"
 cp -r \
+  "$helpers_dir/.bundle" \
   "$helpers_dir/lib" \
   "$helpers_dir/monkey_patches" \
   "$helpers_dir/run.rb" \
+  "$helpers_dir/Gemfile" \
   "$install_dir"
 
 cd "$install_dir"
+
+# NOTE: Sets `BUNDLED WITH` to match the installed v1 version in Gemfile.lock
+# forcing specs and native helpers to run with the same version
+BUNDLER_VERSION=1 bundle install
diff --git a/bundler/helpers/lib/functions.rb b/bundler/helpers/v1/lib/functions.rb
similarity index 100%
rename from bundler/helpers/lib/functions.rb
rename to bundler/helpers/v1/lib/functions.rb
diff --git a/bundler/helpers/lib/functions/conflicting_dependency_resolver.rb b/bundler/helpers/v1/lib/functions/conflicting_dependency_resolver.rb
similarity index 100%
rename from bundler/helpers/lib/functions/conflicting_dependency_resolver.rb
rename to bundler/helpers/v1/lib/functions/conflicting_dependency_resolver.rb
diff --git a/bundler/helpers/lib/functions/dependency_source.rb b/bundler/helpers/v1/lib/functions/dependency_source.rb
similarity index 100%
rename from bundler/helpers/lib/functions/dependency_source.rb
rename to bundler/helpers/v1/lib/functions/dependency_source.rb
diff --git a/bundler/helpers/lib/functions/file_parser.rb b/bundler/helpers/v1/lib/functions/file_parser.rb
similarity index 100%
rename from bundler/helpers/lib/functions/file_parser.rb
rename to bundler/helpers/v1/lib/functions/file_parser.rb
diff --git a/bundler/helpers/lib/functions/force_updater.rb b/bundler/helpers/v1/lib/functions/force_updater.rb
similarity index 100%
rename from bundler/helpers/lib/functions/force_updater.rb
rename to bundler/helpers/v1/lib/functions/force_updater.rb
diff --git a/bundler/helpers/lib/functions/lockfile_updater.rb b/bundler/helpers/v1/lib/functions/lockfile_updater.rb
similarity index 100%
rename from bundler/helpers/lib/functions/lockfile_updater.rb
rename to bundler/helpers/v1/lib/functions/lockfile_updater.rb
diff --git a/bundler/helpers/lib/functions/version_resolver.rb b/bundler/helpers/v1/lib/functions/version_resolver.rb
similarity index 100%
rename from bundler/helpers/lib/functions/version_resolver.rb
rename to bundler/helpers/v1/lib/functions/version_resolver.rb
diff --git a/bundler/helpers/monkey_patches/definition_bundler_version_patch.rb b/bundler/helpers/v1/monkey_patches/definition_bundler_version_patch.rb
similarity index 100%
rename from bundler/helpers/monkey_patches/definition_bundler_version_patch.rb
rename to bundler/helpers/v1/monkey_patches/definition_bundler_version_patch.rb
diff --git a/bundler/helpers/monkey_patches/definition_ruby_version_patch.rb b/bundler/helpers/v1/monkey_patches/definition_ruby_version_patch.rb
similarity index 100%
rename from bundler/helpers/monkey_patches/definition_ruby_version_patch.rb
rename to bundler/helpers/v1/monkey_patches/definition_ruby_version_patch.rb
diff --git a/bundler/helpers/monkey_patches/git_source_patch.rb b/bundler/helpers/v1/monkey_patches/git_source_patch.rb
similarity index 100%
rename from bundler/helpers/monkey_patches/git_source_patch.rb
rename to bundler/helpers/v1/monkey_patches/git_source_patch.rb
diff --git a/bundler/helpers/run.rb b/bundler/helpers/v1/run.rb
similarity index 100%
rename from bundler/helpers/run.rb
rename to bundler/helpers/v1/run.rb
diff --git a/bundler/lib/dependabot/bundler/file_parser.rb b/bundler/lib/dependabot/bundler/file_parser.rb
index a045f32857..4ff7cac3d8 100644
--- a/bundler/lib/dependabot/bundler/file_parser.rb
+++ b/bundler/lib/dependabot/bundler/file_parser.rb
@@ -5,6 +5,7 @@
 require "dependabot/file_parsers/base"
 require "dependabot/bundler/file_updater/lockfile_updater"
 require "dependabot/bundler/native_helpers"
+require "dependabot/bundler/helpers"
 require "dependabot/bundler/version"
 require "dependabot/shared_helpers"
 require "dependabot/errors"
@@ -129,8 +130,8 @@ def parsed_gemfile
                                                       repo_contents_path) do
             write_temporary_dependency_files
 
-            SharedHelpers.run_helper_subprocess(
-              command: NativeHelpers.helper_path,
+            NativeHelpers.run_bundler_subprocess(
+              bundler_version: bundler_version,
               function: "parsed_gemfile",
               args: {
                 gemfile_name: gemfile.name,
@@ -159,8 +160,8 @@ def parsed_gemspec(file)
                                                       repo_contents_path) do
             write_temporary_dependency_files
 
-            SharedHelpers.run_helper_subprocess(
-              command: NativeHelpers.helper_path,
+            NativeHelpers.run_bundler_subprocess(
+              bundler_version: bundler_version,
               function: "parsed_gemspec",
               args: {
                 gemspec_name: file.name,
@@ -298,6 +299,10 @@ def imported_ruby_files
           select { |f| f.name.end_with?(".rb") }.
           reject { |f| f.name == "gems.rb" }
       end
+
+      def bundler_version
+        @bundler_version ||= Helpers.bundler_version(lockfile)
+      end
     end
   end
 end
diff --git a/bundler/lib/dependabot/bundler/file_updater.rb b/bundler/lib/dependabot/bundler/file_updater.rb
index c9a88441a2..d22427f074 100644
--- a/bundler/lib/dependabot/bundler/file_updater.rb
+++ b/bundler/lib/dependabot/bundler/file_updater.rb
@@ -3,6 +3,7 @@
 require "dependabot/file_updaters"
 require "dependabot/file_updaters/base"
 require "dependabot/bundler/native_helpers"
+require "dependabot/bundler/helpers"
 require "dependabot/file_updaters/vendor_updater"
 
 module Dependabot
@@ -75,8 +76,8 @@ def vendor_cache_dir
         return @vendor_cache_dir if defined?(@vendor_cache_dir)
 
         @vendor_cache_dir =
-          SharedHelpers.run_helper_subprocess(
-            command: NativeHelpers.helper_path,
+          NativeHelpers.run_bundler_subprocess(
+            bundler_version: bundler_version,
             function: "vendor_cache_dir",
             args: {
               dir: repo_contents_path
@@ -159,6 +160,10 @@ def top_level_gemspecs
           select { |file| file.name.end_with?(".gemspec") }.
           reject(&:support_file?)
       end
+
+      def bundler_version
+        @bundler_version ||= Helpers.bundler_version(lockfile)
+      end
     end
   end
 end
diff --git a/bundler/lib/dependabot/bundler/file_updater/lockfile_updater.rb b/bundler/lib/dependabot/bundler/file_updater/lockfile_updater.rb
index 8d9a57ea2d..ec2d6ec9b0 100644
--- a/bundler/lib/dependabot/bundler/file_updater/lockfile_updater.rb
+++ b/bundler/lib/dependabot/bundler/file_updater/lockfile_updater.rb
@@ -6,6 +6,7 @@
 require "dependabot/errors"
 require "dependabot/bundler/file_updater"
 require "dependabot/bundler/native_helpers"
+require "dependabot/bundler/helpers"
 
 module Dependabot
   module Bundler
@@ -64,8 +65,8 @@ def build_updated_lockfile
             ) do |tmp_dir|
               write_temporary_dependency_files
 
-              SharedHelpers.run_helper_subprocess(
-                command: NativeHelpers.helper_path,
+              NativeHelpers.run_bundler_subprocess(
+                bundler_version: bundler_version,
                 function: "update_lockfile",
                 args: {
                   gemfile_name: gemfile.name,
@@ -301,6 +302,10 @@ def using_bundler2?
 
           lockfile.content.match?(/BUNDLED WITH\s+2/m)
         end
+
+        def bundler_version
+          @bundler_version ||= Helpers.bundler_version(lockfile)
+        end
       end
     end
   end
diff --git a/bundler/lib/dependabot/bundler/helpers.rb b/bundler/lib/dependabot/bundler/helpers.rb
new file mode 100644
index 0000000000..ef1e6b7ebe
--- /dev/null
+++ b/bundler/lib/dependabot/bundler/helpers.rb
@@ -0,0 +1,16 @@
+# frozen_string_literal: true
+
+module Dependabot
+  module Bundler
+    module Helpers
+      V1 = "1"
+      V2 = "2"
+
+      # TODO: Add support for bundler v2
+      # return "v2" if lockfile.content.match?(/BUNDLED WITH\s+2/m)
+      def self.bundler_version(_lockfile)
+        V1
+      end
+    end
+  end
+end
diff --git a/bundler/lib/dependabot/bundler/native_helpers.rb b/bundler/lib/dependabot/bundler/native_helpers.rb
index 315fc55c42..1b743597b9 100644
--- a/bundler/lib/dependabot/bundler/native_helpers.rb
+++ b/bundler/lib/dependabot/bundler/native_helpers.rb
@@ -1,10 +1,35 @@
 # frozen_string_literal: true
 
+require "bundler"
+require "dependabot/shared_helpers"
+
 module Dependabot
   module Bundler
     module NativeHelpers
-      def self.helper_path
-        "bundle exec ruby #{File.join(native_helpers_root, 'run.rb')}"
+      def self.run_bundler_subprocess(function:, args:, bundler_version:)
+        # Run helper suprocess with all bundler-related ENV variables removed
+        ::Bundler.with_original_env do
+          SharedHelpers.run_helper_subprocess(
+            command: helper_path(bundler_version: bundler_version),
+            function: function,
+            args: args,
+            env: {
+              # Bundler will pick the matching installed major version
+              "BUNDLER_VERSION" => bundler_version,
+              "BUNDLE_GEMFILE" => File.join(versioned_helper_path(bundler_version: bundler_version), "Gemfile"),
+              "BUNDLE_PATH" => File.join(versioned_helper_path(bundler_version: bundler_version), ".bundle")
+            }
+          )
+        end
+      end
+
+      def self.versioned_helper_path(bundler_version:)
+        native_helper_version = "v#{bundler_version}"
+        File.join(native_helpers_root, native_helper_version)
+      end
+
+      def self.helper_path(bundler_version:)
+        "ruby #{File.join(versioned_helper_path(bundler_version: bundler_version), 'run.rb')}"
       end
 
       def self.native_helpers_root
diff --git a/bundler/lib/dependabot/bundler/update_checker/conflicting_dependency_resolver.rb b/bundler/lib/dependabot/bundler/update_checker/conflicting_dependency_resolver.rb
index 4cf7fbef28..a78c3544ca 100644
--- a/bundler/lib/dependabot/bundler/update_checker/conflicting_dependency_resolver.rb
+++ b/bundler/lib/dependabot/bundler/update_checker/conflicting_dependency_resolver.rb
@@ -2,6 +2,7 @@
 
 require "dependabot/bundler/update_checker"
 require "dependabot/bundler/native_helpers"
+require "dependabot/bundler/helpers"
 require "dependabot/shared_helpers"
 
 module Dependabot
@@ -28,8 +29,8 @@ def initialize(dependency_files:, repo_contents_path:, credentials:)
         #   * requirement [String] the requirement on the target_dependency
         def conflicting_dependencies(dependency:, target_version:)
           in_a_native_bundler_context(error_handling: false) do |tmp_dir|
-            SharedHelpers.run_helper_subprocess(
-              command: NativeHelpers.helper_path,
+            NativeHelpers.run_bundler_subprocess(
+              bundler_version: bundler_version,
               function: "conflicting_dependencies",
               args: {
                 dir: tmp_dir,
@@ -42,6 +43,12 @@ def conflicting_dependencies(dependency:, target_version:)
             )
           end
         end
+
+        private
+
+        def bundler_version
+          @bundler_version ||= Helpers.bundler_version(lockfile)
+        end
       end
     end
   end
diff --git a/bundler/lib/dependabot/bundler/update_checker/force_updater.rb b/bundler/lib/dependabot/bundler/update_checker/force_updater.rb
index feeb0d1b78..cfd5f32c29 100644
--- a/bundler/lib/dependabot/bundler/update_checker/force_updater.rb
+++ b/bundler/lib/dependabot/bundler/update_checker/force_updater.rb
@@ -3,6 +3,7 @@
 require "dependabot/bundler/file_parser"
 require "dependabot/bundler/file_updater/lockfile_updater"
 require "dependabot/bundler/native_helpers"
+require "dependabot/bundler/helpers"
 require "dependabot/bundler/update_checker"
 require "dependabot/bundler/update_checker/requirements_updater"
 require "dependabot/errors"
@@ -43,8 +44,8 @@ def update_multiple_dependencies?
 
         def force_update
           in_a_native_bundler_context(error_handling: false) do |tmp_dir|
-            updated_deps, specs = SharedHelpers.run_helper_subprocess(
-              command: NativeHelpers.helper_path,
+            updated_deps, specs = NativeHelpers.run_bundler_subprocess(
+              bundler_version: bundler_version,
               function: "force_update",
               args: {
                 dir: tmp_dir,
@@ -146,6 +147,10 @@ def using_bundler2?
 
           lockfile.content.match?(/BUNDLED WITH\s+2/m)
         end
+
+        def bundler_version
+          @bundler_version ||= Helpers.bundler_version(lockfile)
+        end
       end
     end
   end
diff --git a/bundler/lib/dependabot/bundler/update_checker/latest_version_finder/dependency_source.rb b/bundler/lib/dependabot/bundler/update_checker/latest_version_finder/dependency_source.rb
index e51887e4f3..2943ba0b05 100644
--- a/bundler/lib/dependabot/bundler/update_checker/latest_version_finder/dependency_source.rb
+++ b/bundler/lib/dependabot/bundler/update_checker/latest_version_finder/dependency_source.rb
@@ -1,5 +1,8 @@
 # frozen_string_literal: true
 
+require "dependabot/bundler/native_helpers"
+require "dependabot/bundler/helpers"
+
 module Dependabot
   module Bundler
     class UpdateChecker
@@ -53,8 +56,8 @@ def latest_git_version_details
 
             SharedHelpers.with_git_configured(credentials: credentials) do
               in_a_native_bundler_context do |tmp_dir|
-                SharedHelpers.run_helper_subprocess(
-                  command: NativeHelpers.helper_path,
+                NativeHelpers.run_bundler_subprocess(
+                  bundler_version: bundler_version,
                   function: "depencency_source_latest_git_version",
                   args: {
                     dir: tmp_dir,
@@ -98,8 +101,8 @@ def dependency_rubygems_uri
           def private_registry_versions
             @private_registry_versions ||=
               in_a_native_bundler_context do |tmp_dir|
-                SharedHelpers.run_helper_subprocess(
-                  command: NativeHelpers.helper_path,
+                NativeHelpers.run_bundler_subprocess(
+                  bundler_version: bundler_version,
                   function: "private_registry_versions",
                   args: {
                     dir: tmp_dir,
@@ -118,8 +121,8 @@ def source_type
             return @source_type = RUBYGEMS unless gemfile
 
             @source_type = in_a_native_bundler_context do |tmp_dir|
-              SharedHelpers.run_helper_subprocess(
-                command: NativeHelpers.helper_path,
+              NativeHelpers.run_bundler_subprocess(
+                bundler_version: bundler_version,
                 function: "dependency_source_type",
                 args: {
                   dir: tmp_dir,
@@ -135,6 +138,15 @@ def gemfile
             dependency_files.find { |f| f.name == "Gemfile" } ||
               dependency_files.find { |f| f.name == "gems.rb" }
           end
+
+          def lockfile
+            dependency_files.find { |f| f.name == "Gemfile.lock" } ||
+              dependency_files.find { |f| f.name == "gems.locked" }
+          end
+
+          def bundler_version
+            @bundler_version ||= Helpers.bundler_version(lockfile)
+          end
         end
       end
     end
diff --git a/bundler/lib/dependabot/bundler/update_checker/shared_bundler_helpers.rb b/bundler/lib/dependabot/bundler/update_checker/shared_bundler_helpers.rb
index a6c04a7da2..9583332300 100644
--- a/bundler/lib/dependabot/bundler/update_checker/shared_bundler_helpers.rb
+++ b/bundler/lib/dependabot/bundler/update_checker/shared_bundler_helpers.rb
@@ -4,6 +4,7 @@
 
 require "dependabot/bundler/update_checker"
 require "dependabot/bundler/native_helpers"
+require "dependabot/bundler/helpers"
 require "dependabot/shared_helpers"
 require "dependabot/errors"
 
@@ -163,8 +164,8 @@ def handle_bundler_errors(error)
 
         def inaccessible_git_dependencies
           in_a_native_bundler_context(error_handling: false) do |tmp_dir|
-            git_specs = SharedHelpers.run_helper_subprocess(
-              command: NativeHelpers.helper_path,
+            git_specs = NativeHelpers.run_bundler_subprocess(
+              bundler_version: bundler_version,
               function: "git_specs",
               args: {
                 dir: tmp_dir,
@@ -187,8 +188,8 @@ def inaccessible_git_dependencies
 
         def jfrog_source
           in_a_native_bundler_context(error_handling: false) do |dir|
-            SharedHelpers.run_helper_subprocess(
-              command: NativeHelpers.helper_path,
+            NativeHelpers.run_bundler_subprocess(
+              bundler_version: bundler_version,
               function: "jfrog_source",
               args: {
                 dir: dir,
@@ -236,6 +237,10 @@ def using_bundler2?
 
           lockfile.content.match?(/BUNDLED WITH\s+2/m)
         end
+
+        def bundler_version
+          @bundler_version ||= Helpers.bundler_version(lockfile)
+        end
       end
     end
   end
diff --git a/bundler/lib/dependabot/bundler/update_checker/version_resolver.rb b/bundler/lib/dependabot/bundler/update_checker/version_resolver.rb
index 3cdce23605..a482b26967 100644
--- a/bundler/lib/dependabot/bundler/update_checker/version_resolver.rb
+++ b/bundler/lib/dependabot/bundler/update_checker/version_resolver.rb
@@ -2,6 +2,7 @@
 
 require "excon"
 
+require "dependabot/bundler/helpers"
 require "dependabot/bundler/update_checker"
 require "dependabot/bundler/file_updater/lockfile_updater"
 require "dependabot/bundler/requirement"
@@ -75,8 +76,8 @@ def fetch_latest_resolvable_version_details
             # some errors we want to handle specifically ourselves, including
             # potentially retrying in the case of the Ruby version being locked
             in_a_native_bundler_context(error_handling: false) do |tmp_dir|
-              details =  SharedHelpers.run_helper_subprocess(
-                command: NativeHelpers.helper_path,
+              details = NativeHelpers.run_bundler_subprocess(
+                bundler_version: bundler_version,
                 function: "resolve_version",
                 args: {
                   dependency_name: dependency.name,
@@ -218,6 +219,10 @@ def using_bundler2?
 
           lockfile.content.match?(/BUNDLED WITH\s+2/m)
         end
+
+        def bundler_version
+          @bundler_version ||= Helpers.bundler_version(lockfile)
+        end
       end
     end
   end
diff --git a/bundler/spec/dependabot/bundler/update_checker/latest_version_finder_spec.rb b/bundler/spec/dependabot/bundler/update_checker/latest_version_finder_spec.rb
index ecfe8bd7f9..b831824a98 100644
--- a/bundler/spec/dependabot/bundler/update_checker/latest_version_finder_spec.rb
+++ b/bundler/spec/dependabot/bundler/update_checker/latest_version_finder_spec.rb
@@ -241,18 +241,18 @@
       before do
         # We only need to stub out the version callout since it would
         # otherwise call out to the internet in a shell command
-        allow(Dependabot::SharedHelpers).
-          to receive(:run_helper_subprocess).
+        allow(Dependabot::Bundler::NativeHelpers).
+          to receive(:run_bundler_subprocess).
           with({
-                 command: Dependabot::Bundler::NativeHelpers.helper_path,
+                 bundler_version: "1",
                  function: "dependency_source_type",
                  args: anything
                }).and_call_original
 
-        allow(Dependabot::SharedHelpers).
-          to receive(:run_helper_subprocess).
+        allow(Dependabot::Bundler::NativeHelpers).
+          to receive(:run_bundler_subprocess).
           with({
-                 command: Dependabot::Bundler::NativeHelpers.helper_path,
+                 bundler_version: "1",
                  function: "private_registry_versions",
                  args: anything
                }).
@@ -297,10 +297,10 @@
         end
 
         before do
-          allow(Dependabot::SharedHelpers).
-            to receive(:run_helper_subprocess).
+          allow(Dependabot::Bundler::NativeHelpers).
+            to receive(:run_bundler_subprocess).
             with({
-                   command: Dependabot::Bundler::NativeHelpers.helper_path,
+                   bundler_version: "1",
                    function: "private_registry_versions",
                    args: anything
                  }).
@@ -330,10 +330,10 @@
         end
 
         before do
-          allow(Dependabot::SharedHelpers).
-            to receive(:run_helper_subprocess).
+          allow(Dependabot::Bundler::NativeHelpers).
+            to receive(:run_bundler_subprocess).
             with({
-                   command: Dependabot::Bundler::NativeHelpers.helper_path,
+                   bundler_version: "1",
                    function: "private_registry_versions",
                    args: anything
                  }).
@@ -363,10 +363,10 @@
         end
 
         before do
-          allow(Dependabot::SharedHelpers).
-            to receive(:run_helper_subprocess).
+          allow(Dependabot::Bundler::NativeHelpers).
+            to receive(:run_bundler_subprocess).
             with({
-                   command: Dependabot::Bundler::NativeHelpers.helper_path,
+                   bundler_version: "1",
                    function: "private_registry_versions",
                    args: anything
                  }).
@@ -385,10 +385,10 @@
 
       context "that doesn't have details of the gem" do
         before do
-          allow(Dependabot::SharedHelpers).
-            to receive(:run_helper_subprocess).
+          allow(Dependabot::Bundler::NativeHelpers).
+            to receive(:run_bundler_subprocess).
             with({
-                   command: Dependabot::Bundler::NativeHelpers.helper_path,
+                   bundler_version: "1",
                    function: "private_registry_versions",
                    args: anything
                  }).
@@ -540,18 +540,18 @@
       before do
         # We only need to stub out the version callout since it would
         # otherwise call out to the internet in a shell command
-        allow(Dependabot::SharedHelpers).
-          to receive(:run_helper_subprocess).
+        allow(Dependabot::Bundler::NativeHelpers).
+          to receive(:run_bundler_subprocess).
           with({
-                 command: Dependabot::Bundler::NativeHelpers.helper_path,
+                 bundler_version: "1",
                  function: "dependency_source_type",
                  args: anything
                }).and_call_original
 
-        allow(Dependabot::SharedHelpers).
-          to receive(:run_helper_subprocess).
+        allow(Dependabot::Bundler::NativeHelpers).
+          to receive(:run_bundler_subprocess).
           with({
-                 command: Dependabot::Bundler::NativeHelpers.helper_path,
+                 bundler_version: "1",
                  function: "private_registry_versions",
                  args: anything
                }).
diff --git a/bundler/spec/dependabot/bundler/update_checker/version_resolver_spec.rb b/bundler/spec/dependabot/bundler/update_checker/version_resolver_spec.rb
index 2656b19481..b84aee382f 100644
--- a/bundler/spec/dependabot/bundler/update_checker/version_resolver_spec.rb
+++ b/bundler/spec/dependabot/bundler/update_checker/version_resolver_spec.rb
@@ -188,10 +188,10 @@
           end
 
           before do
-            allow(Dependabot::SharedHelpers).
-              to receive(:run_helper_subprocess).
+            allow(Dependabot::Bundler::NativeHelpers).
+              to receive(:run_bundler_subprocess).
               with({
-                     command: Dependabot::Bundler::NativeHelpers.helper_path,
+                     bundler_version: "1",
                      function: "resolve_version",
                      args: anything
                    }).
diff --git a/bundler/spec/dependabot/bundler/update_checker_spec.rb b/bundler/spec/dependabot/bundler/update_checker_spec.rb
index 2176b7dd07..c5a098d496 100644
--- a/bundler/spec/dependabot/bundler/update_checker_spec.rb
+++ b/bundler/spec/dependabot/bundler/update_checker_spec.rb
@@ -195,18 +195,18 @@
       before do
         # We only need to stub out the version callout since it would
         # otherwise call out to the internet in a shell command
-        allow(Dependabot::SharedHelpers).
-          to receive(:run_helper_subprocess).
+        allow(Dependabot::Bundler::NativeHelpers).
+          to receive(:run_bundler_subprocess).
           with({
-                 command: Dependabot::Bundler::NativeHelpers.helper_path,
+                 bundler_version: "1",
                  function: "dependency_source_type",
                  args: anything
                }).and_call_original
 
-        allow(Dependabot::SharedHelpers).
-          to receive(:run_helper_subprocess).
+        allow(Dependabot::Bundler::NativeHelpers).
+          to receive(:run_bundler_subprocess).
           with({
-                 command: Dependabot::Bundler::NativeHelpers.helper_path,
+                 bundler_version: "1",
                  function: "private_registry_versions",
                  args: anything
                }).
diff --git a/bundler/spec/fixtures/projects/bundler1/gemspec_with_require_no_lockfile/example.gemspec b/bundler/spec/fixtures/projects/bundler1/gemspec_with_require_no_lockfile/example.gemspec
index c520a97a69..705e935a3a 100644
--- a/bundler/spec/fixtures/projects/bundler1/gemspec_with_require_no_lockfile/example.gemspec
+++ b/bundler/spec/fixtures/projects/bundler1/gemspec_with_require_no_lockfile/example.gemspec
@@ -1,5 +1,7 @@
 # frozen_string_literal: true
 
+require "find"
+
 lib = File.expand_path("lib", __dir__)
 $LOAD_PATH.unshift(lib) unless $LOAD_PATH.include?(lib)
 require "example/version"
diff --git a/bundler/spec/fixtures/projects/bundler1/imports_gemspec_with_require/example.gemspec b/bundler/spec/fixtures/projects/bundler1/imports_gemspec_with_require/example.gemspec
index c520a97a69..705e935a3a 100644
--- a/bundler/spec/fixtures/projects/bundler1/imports_gemspec_with_require/example.gemspec
+++ b/bundler/spec/fixtures/projects/bundler1/imports_gemspec_with_require/example.gemspec
@@ -1,5 +1,7 @@
 # frozen_string_literal: true
 
+require "find"
+
 lib = File.expand_path("lib", __dir__)
 $LOAD_PATH.unshift(lib) unless $LOAD_PATH.include?(lib)
 require "example/version"
diff --git a/bundler/spec/native_spec_helper.rb b/bundler/spec/native_spec_helper.rb
index 39c1d77d11..01d15ebfe7 100644
--- a/bundler/spec/native_spec_helper.rb
+++ b/bundler/spec/native_spec_helper.rb
@@ -2,8 +2,8 @@
 
 require "spec_helper"
 
-$LOAD_PATH.unshift(File.expand_path("../helpers/lib", __dir__))
-$LOAD_PATH.unshift(File.expand_path("../helpers/monkey_patches", __dir__))
+$LOAD_PATH.unshift(File.expand_path("../helpers/v1/lib", __dir__))
+$LOAD_PATH.unshift(File.expand_path("../helpers/v1/monkey_patches", __dir__))
 
 # Bundler monkey patches
 require "definition_ruby_version_patch"
diff --git a/common/lib/dependabot/shared_helpers.rb b/common/lib/dependabot/shared_helpers.rb
index b6d0724016..82ea8e5fde 100644
--- a/common/lib/dependabot/shared_helpers.rb
+++ b/common/lib/dependabot/shared_helpers.rb
@@ -75,13 +75,17 @@ def self.run_helper_subprocess(command:, function:, args:, env: nil,
       start = Time.now
       stdin_data = JSON.dump(function: function, args: args)
       cmd = allow_unsafe_shell_command ? command : escape_command(command)
-      env_cmd = [env, cmd].compact
+
+      # NOTE: For debugging native helpers in specs and dry-run: outputs the
+      # bash command to run in the tmp directory created by
+      # in_a_temporary_directory
       if ENV["DEBUG_FUNCTION"] == function
-        escaped_stdin_data = stdin_data.gsub("\"", "\\\"")
-        puts "$ cd #{Dir.pwd} && echo \"#{escaped_stdin_data}\" | #{env_cmd.join(' ')}"
+        puts helper_subprocess_bash_command(stdin_data: stdin_data, command: cmd, env: env)
         # Pause execution so we can run helpers inside the temporary directory
         byebug # rubocop:disable Lint/Debugger
       end
+
+      env_cmd = [env, cmd].compact
       stdout, stderr, process = Open3.capture3(*env_cmd, stdin_data: stdin_data)
       time_taken = Time.now - start
 
@@ -286,5 +290,12 @@ def self.run_shell_command(command, allow_unsafe_shell_command: false)
         error_context: error_context
       )
     end
+
+    def self.helper_subprocess_bash_command(command:, stdin_data:, env:)
+      escaped_stdin_data = stdin_data.gsub("\"", "\\\"")
+      env_keys = env ? env.compact.map { |k, v| "#{k}=#{v}" }.join(" ") + " " : ""
+      "$ cd #{Dir.pwd} && echo \"#{escaped_stdin_data}\" | #{env_keys}#{command}"
+    end
+    private_class_method :helper_subprocess_bash_command
   end
 end