diff --git a/.rubocop.yml b/.rubocop.yml
index 3a9503f0..ed7f1565 100644
--- a/.rubocop.yml
+++ b/.rubocop.yml
@@ -14,7 +14,6 @@ AllCops:
     - "*/spec/fixtures/**/*"
     - "vendor/**/*"
     - "dry-run/**/*"
-    - "bundler/helpers/v1/patched_bundler"
     - "bundler/helpers/spec_helpers/*"
   NewCops: enable
   TargetRubyVersion: 3.1
diff --git a/.rubocop_todo.yml b/.rubocop_todo.yml
index 64ea1d09..e7673987 100644
--- a/.rubocop_todo.yml
+++ b/.rubocop_todo.yml
@@ -9,7 +9,6 @@
 # Offense count: 39
 RSpec/AnyInstance:
   Exclude:
-    - 'bundler/helpers/v1/spec/shared_contexts.rb'
     - 'bundler/spec/dependabot/bundler/update_checker_spec.rb'
     - 'common/spec/dependabot/clients/codecommit_spec.rb'
     - 'common/spec/dependabot/file_fetchers/base_spec.rb'
diff --git a/updater/lib/dependabot/dependency_snapshot.rb b/updater/lib/dependabot/dependency_snapshot.rb
index b9c2c853..02b03c4e 100644
--- a/updater/lib/dependabot/dependency_snapshot.rb
+++ b/updater/lib/dependabot/dependency_snapshot.rb
@@ -241,8 +241,10 @@ def dependency_file_parser
         reject_external_code: job.reject_external_code?,
         options: job.experiments
       )
-      # Add 'package_manager' to the depedency_snapshopt to use it in operations'
+      # Add 'package_manager' to the dependency_snapshot to use it in operations
       package_manager = parser.package_manager
+      # Raise an error if the package manager version is unsupported
+      package_manager&.raise_if_unsupported!
 
       @package_manager[@current_directory] = package_manager
 
diff --git a/updater/lib/dependabot/notices_helpers.rb b/updater/lib/dependabot/notices_helpers.rb
index b5a646c0..c8f52474 100644
--- a/updater/lib/dependabot/notices_helpers.rb
+++ b/updater/lib/dependabot/notices_helpers.rb
@@ -60,9 +60,6 @@ def log_notice(notice)
 
     sig { params(package_manager: T.nilable(PackageManagerBase)).returns(T.nilable(Dependabot::Notice)) }
     def create_deprecation_notice(package_manager)
-      # Feature flag check if deprecation notice should be added to notices.
-      return unless Dependabot::Experiments.enabled?(:add_deprecation_warn_to_pr_message)
-
       return unless package_manager
 
       return unless package_manager.is_a?(PackageManagerBase)
diff --git a/updater/lib/dependabot/update_files_command.rb b/updater/lib/dependabot/update_files_command.rb
index b3cb91d7..d04b4abc 100644
--- a/updater/lib/dependabot/update_files_command.rb
+++ b/updater/lib/dependabot/update_files_command.rb
@@ -67,7 +67,7 @@ def base_commit_sha
       Environment.job_definition["base_commit_sha"]
     end
 
-    # rubocop:disable Metrics/AbcSize, Layout/LineLength
+    # rubocop:disable Metrics/AbcSize, Layout/LineLength, Metrics/MethodLength
     def handle_parser_error(error)
       # This happens if the repo gets removed after a job gets kicked off.
       # The service will handle the removal without any prompt from the updater,
@@ -80,6 +80,16 @@ def handle_parser_error(error)
         # Check if the error is a known "run halting" state we should handle
         if (error_type = Updater::ErrorHandler::RUN_HALTING_ERRORS[error.class])
           { "error-type": error_type }
+        elsif error.is_a?(ToolVersionNotSupported)
+          Dependabot.logger.error(error.message)
+          {
+            "error-type": "tool_version_not_supported",
+            "error-detail": {
+              "tool-name": error.tool_name,
+              "detected-version": error.detected_version,
+              "supported-versions": error.supported_versions
+            }
+          }
         else
           # If it isn't, then log all the details and let the application error
           # tracker know about it
@@ -118,6 +128,6 @@ def handle_parser_error(error)
         error_details: error_details[:"error-detail"]
       )
     end
-    # rubocop:enable Metrics/AbcSize, Layout/LineLength
+    # rubocop:enable Metrics/AbcSize, Layout/LineLength, Metrics/MethodLength
   end
 end
diff --git a/updater/lib/dependabot/updater/group_update_creation.rb b/updater/lib/dependabot/updater/group_update_creation.rb
index 9494698c..abf23f64 100644
--- a/updater/lib/dependabot/updater/group_update_creation.rb
+++ b/updater/lib/dependabot/updater/group_update_creation.rb
@@ -241,9 +241,6 @@ def compile_updates_for(dependency, dependency_files, group) # rubocop:disable M
           return []
         end
 
-        # Raise an error if the package manager version is unsupported
-        dependency_snapshot.package_manager&.raise_if_unsupported!
-
         checker.updated_dependencies(
           requirements_to_unlock: requirements_to_unlock
         )
diff --git a/updater/lib/dependabot/updater/operations/create_security_update_pull_request.rb b/updater/lib/dependabot/updater/operations/create_security_update_pull_request.rb
index d10754aa..156a48f3 100644
--- a/updater/lib/dependabot/updater/operations/create_security_update_pull_request.rb
+++ b/updater/lib/dependabot/updater/operations/create_security_update_pull_request.rb
@@ -105,7 +105,6 @@ def check_and_create_pr_with_error_handling(dependency)
         # rubocop:disable Metrics/AbcSize
         # rubocop:disable Metrics/PerceivedComplexity
         # rubocop:disable Metrics/MethodLength
-        # rubocop:disable Metrics/CyclomaticComplexity
         sig { params(dependency: Dependabot::Dependency).void }
         def check_and_create_pull_request(dependency)
           dependency = vulnerable_version(dependency) if dependency.metadata[:all_versions]
@@ -146,9 +145,6 @@ def check_and_create_pull_request(dependency)
           log_requirements_for_update(requirements_to_unlock, checker)
           return record_security_update_not_possible_error(checker) if requirements_to_unlock == :update_not_possible
 
-          # Raise an error if the package manager version is unsupported
-          dependency_snapshot.package_manager&.raise_if_unsupported!
-
           updated_deps = checker.updated_dependencies(
             requirements_to_unlock: requirements_to_unlock
           )
@@ -202,7 +198,6 @@ def check_and_create_pull_request(dependency)
         # rubocop:enable Metrics/MethodLength
         # rubocop:enable Metrics/AbcSize
         # rubocop:enable Metrics/PerceivedComplexity
-        # rubocop:enable Metrics/CyclomaticComplexity
         sig { params(dependency: Dependabot::Dependency).returns(Dependabot::Dependency) }
         def vulnerable_version(dependency)
           return dependency if dependency.metadata[:all_versions].count == 1
diff --git a/updater/lib/dependabot/updater/operations/refresh_security_update_pull_request.rb b/updater/lib/dependabot/updater/operations/refresh_security_update_pull_request.rb
index 6202dc7a..9acbffc8 100644
--- a/updater/lib/dependabot/updater/operations/refresh_security_update_pull_request.rb
+++ b/updater/lib/dependabot/updater/operations/refresh_security_update_pull_request.rb
@@ -54,9 +54,6 @@ def perform
           Dependabot.logger.info("Starting update job for #{job.source.repo}")
           Dependabot.logger.info("Checking and updating security pull requests...")
 
-          # Raise an error if the package manager version is unsupported
-          dependency_snapshot.package_manager&.raise_if_unsupported!
-
           # Retrieve the list of initial notices from dependency snapshot
           @notices = dependency_snapshot.notices
           # More notices can be added during the update process
@@ -132,7 +129,28 @@ def check_and_update_pull_request(dependencies)
           # Note: Gradle, Maven and Nuget dependency names can be case-insensitive
           # and the dependency name in the security advisory often doesn't match
           # what users have specified in their manifest.
-          lead_dep_name = job_dependencies.first&.downcase
+          # Dependabot::Experiments.register(:lead_security_dependency, true)
+
+          if Dependabot::Experiments.enabled?(:lead_security_dependency)
+            lead_dep_name = security_advisory_dependency
+
+            # telemetry data collection
+            Dependabot.logger.info(
+              "Security advisory dependency: #{lead_dep_name}\n" \
+              "First dependency in list: #{job_dependencies.first&.downcase}"
+            )
+
+            if lead_dep_name != job_dependencies.first&.downcase
+              Dependabot.logger.info(
+                "Difference found between security-advisory (#{lead_dep_name}) and " \
+                "first-dependency (#{job_dependencies.first&.downcase})"
+              )
+            end
+
+          else
+            lead_dep_name = job_dependencies.first&.downcase
+          end
+
           lead_dependency = dependencies.find do |dep|
             dep.name.downcase == lead_dep_name
           end
@@ -174,7 +192,9 @@ def check_and_update_pull_request(dependencies)
           # and the dependency name in the security advisory often doesn't match
           # what users have specified in their manifest.
           job_dependencies = job_dependencies.map(&:downcase)
-          if dependency_change.updated_dependencies.map { |x| x.name.downcase } != job_dependencies
+          changed_dependencies = dependency_change.updated_dependencies.map { |x| x.name.downcase }
+
+          if changed_dependencies.sort_by(&:downcase) != job_dependencies.sort_by(&:downcase)
             # The dependencies being updated have changed. Close the existing
             # multi-dependency PR and try creating a new one.
             close_pull_request(reason: :dependencies_changed)
@@ -288,6 +308,11 @@ def close_pull_request(reason:)
 
           service.close_pull_request(job_dependencies, reason)
         end
+
+        sig { returns(String) }
+        def security_advisory_dependency
+          T.cast(job.security_advisories.first, T::Hash[String, String])["dependency-name"].to_s
+        end
       end
     end
   end
diff --git a/updater/lib/dependabot/updater/operations/refresh_version_update_pull_request.rb b/updater/lib/dependabot/updater/operations/refresh_version_update_pull_request.rb
index 4919c758..aafa2b2e 100644
--- a/updater/lib/dependabot/updater/operations/refresh_version_update_pull_request.rb
+++ b/updater/lib/dependabot/updater/operations/refresh_version_update_pull_request.rb
@@ -138,9 +138,6 @@ def check_and_update_pull_request(dependencies)
             return close_pull_request(reason: :update_no_longer_possible)
           end
 
-          # Raise an error if the package manager version is unsupported
-          dependency_snapshot.package_manager&.raise_if_unsupported!
-
           updated_deps = checker.updated_dependencies(
             requirements_to_unlock: requirements_to_unlock
           )
diff --git a/updater/lib/dependabot/updater/operations/update_all_versions.rb b/updater/lib/dependabot/updater/operations/update_all_versions.rb
index 40e63264..bdcc9a20 100644
--- a/updater/lib/dependabot/updater/operations/update_all_versions.rb
+++ b/updater/lib/dependabot/updater/operations/update_all_versions.rb
@@ -172,9 +172,6 @@ def check_and_create_pull_request(dependency)
             notices: @notices
           )
 
-          # Raise an error if the package manager version is unsupported
-          dependency_snapshot.package_manager&.raise_if_unsupported!
-
           if dependency_change.updated_dependency_files.empty?
             raise "UpdateChecker found viable dependencies to be updated, but FileUpdater failed to update any files"
           end
diff --git a/updater/spec/dependabot/update_files_command_spec.rb b/updater/spec/dependabot/update_files_command_spec.rb
index 20a31a06..db17767e 100644
--- a/updater/spec/dependabot/update_files_command_spec.rb
+++ b/updater/spec/dependabot/update_files_command_spec.rb
@@ -3,6 +3,7 @@
 
 require "spec_helper"
 require "dependabot/update_files_command"
+require "dependabot/bundler"
 require "tmpdir"
 
 RSpec.describe Dependabot::UpdateFilesCommand do
@@ -112,6 +113,32 @@
       end
     end
 
+    context "when there is an unsupported package manager version" do
+      let(:error) do
+        Dependabot::ToolVersionNotSupported.new(
+          "bundler",       # tool name
+          "1.0.0",         # detected version
+          ">= 2.0.0"       # supported versions
+        )
+      end
+
+      it_behaves_like "a fast-failed job"
+
+      it "records the unsupported version error with details" do
+        expect(service).to receive(:record_update_job_error).with(
+          error_type: "tool_version_not_supported",
+          error_details: {
+            "tool-name": "bundler",
+            "detected-version": "1.0.0",
+            "supported-versions": ">= 2.0.0"
+          }
+        )
+        expect(service).to receive(:mark_job_as_processed)
+
+        perform_job
+      end
+    end
+
     context "with an update files error (cloud)" do
       let(:error) { StandardError.new("hell") }
 
diff --git a/updater/spec/fixtures/bundler/original/Gemfile.lock b/updater/spec/fixtures/bundler/original/Gemfile.lock
index 4fd8f37a..1f21c435 100644
--- a/updater/spec/fixtures/bundler/original/Gemfile.lock
+++ b/updater/spec/fixtures/bundler/original/Gemfile.lock
@@ -13,4 +13,4 @@ DEPENDENCIES
   dummy-pkg-b (~> 1.1.0)
 
 BUNDLED WITH
-   1.14.6
+   2.4.13
diff --git a/updater/spec/fixtures/bundler/original/sub_dep.lock b/updater/spec/fixtures/bundler/original/sub_dep.lock
index dae47db2..e6d6a5d0 100644
--- a/updater/spec/fixtures/bundler/original/sub_dep.lock
+++ b/updater/spec/fixtures/bundler/original/sub_dep.lock
@@ -13,4 +13,4 @@ DEPENDENCIES
   dummy-pkg-b (~> 1.1.0)
 
 BUNDLED WITH
-   1.14.6
+   2.4.13
\ No newline at end of file
diff --git a/updater/spec/fixtures/bundler/updated/Gemfile.lock b/updater/spec/fixtures/bundler/updated/Gemfile.lock
index 0e7697ff..6397df8c 100644
--- a/updater/spec/fixtures/bundler/updated/Gemfile.lock
+++ b/updater/spec/fixtures/bundler/updated/Gemfile.lock
@@ -13,4 +13,4 @@ DEPENDENCIES
   dummy-pkg-b (~> 1.2.0)
 
 BUNDLED WITH
-   1.14.6
+   2.4.13
diff --git a/updater/spec/fixtures/bundler_grouped/original/Gemfile.lock b/updater/spec/fixtures/bundler_grouped/original/Gemfile.lock
index 48feef35..8dc7b0cd 100644
--- a/updater/spec/fixtures/bundler_grouped/original/Gemfile.lock
+++ b/updater/spec/fixtures/bundler_grouped/original/Gemfile.lock
@@ -15,4 +15,4 @@ DEPENDENCIES
   ungrouped-dummy-pkg-c (~> 1.0.0)
 
 BUNDLED WITH
-   1.14.6
+   2.4.13
diff --git a/updater/spec/support/dummy_pkg_helpers.rb b/updater/spec/support/dummy_pkg_helpers.rb
index 2f207f5f..2750b821 100644
--- a/updater/spec/support/dummy_pkg_helpers.rb
+++ b/updater/spec/support/dummy_pkg_helpers.rb
@@ -89,10 +89,8 @@ def deprecated?
 
     sig { override.returns(T::Boolean) }
     def unsupported?
-      # Check if the feature flag for Bundler v1 unsupported error is enabled.
-      return false unless name == "bundler" && Dependabot::Experiments.enabled?(:bundler_v1_unsupported_error)
-
-      version < supported_versions.first
+      # Check if the version is not supported
+      supported_versions.all? { |supported| supported > version }
     end
   end
 end