diff --git a/updater/lib/dependabot/updater/operations/group_update_all_versions.rb b/updater/lib/dependabot/updater/operations/group_update_all_versions.rb
index e07264059d..87e86d738f 100644
--- a/updater/lib/dependabot/updater/operations/group_update_all_versions.rb
+++ b/updater/lib/dependabot/updater/operations/group_update_all_versions.rb
@@ -71,6 +71,8 @@ def perform
         def run_grouped_dependency_updates
           Dependabot.logger.info("Starting grouped update job for #{job.source.repo}")
 
+          Dependabot.logger.info("Found #{dependency_snapshot.groups.count} group(s).")
+
           dependency_snapshot.groups.each do |_group_hash, group|
             Dependabot.logger.info("Starting update group for '#{group.name}'")
 
diff --git a/updater/spec/dependabot/updater/operations/group_update_all_versions_spec.rb b/updater/spec/dependabot/updater/operations/group_update_all_versions_spec.rb
index c336ea85c3..79c67f6490 100644
--- a/updater/spec/dependabot/updater/operations/group_update_all_versions_spec.rb
+++ b/updater/spec/dependabot/updater/operations/group_update_all_versions_spec.rb
@@ -128,6 +128,40 @@
     end
   end
 
+  context "when there are two overlapping groups" do
+    let(:job_definition) do
+      job_definition_fixture("bundler/version_updates/group_update_all_overlapping_groups")
+    end
+
+    let(:dependency_files) do
+      original_bundler_files
+    end
+
+    before do
+      stub_rubygems_calls
+    end
+
+    it "creates a pull request for each containing the same dependencies" do
+      allow(Dependabot.logger).to receive(:info)
+      expect(Dependabot.logger).to receive(:info).with(
+        "Found 2 group(s)."
+      )
+
+      expect(mock_error_handler).not_to receive(:handle_dependabot_error)
+      expect(mock_service).to receive(:create_pull_request) do |dependency_change|
+        expect(dependency_change.dependency_group.name).to eql("my-group")
+        expect(dependency_change.updated_dependency_files_hash).to eql(updated_bundler_files_hash)
+      end
+
+      expect(mock_service).to receive(:create_pull_request) do |dependency_change|
+        expect(dependency_change.dependency_group.name).to eql("my-overlapping-group")
+        expect(dependency_change.updated_dependency_files_hash).to eql(updated_bundler_files_hash)
+      end
+
+      group_update_all.perform
+    end
+  end
+
   context "when nothing in the group needs to be updated" do
     let(:job_definition) do
       job_definition_fixture("bundler/version_updates/group_update_all")
diff --git a/updater/spec/fixtures/job_definitions/bundler/version_updates/group_update_all_overlapping_groups.yaml b/updater/spec/fixtures/job_definitions/bundler/version_updates/group_update_all_overlapping_groups.yaml
new file mode 100644
index 0000000000..1977d2cd94
--- /dev/null
+++ b/updater/spec/fixtures/job_definitions/bundler/version_updates/group_update_all_overlapping_groups.yaml
@@ -0,0 +1,42 @@
+job:
+  package-manager: bundler
+  source:
+    provider: github
+    repo: dependabot/smoke-tests
+    directory: "/bundler"
+    branch:
+    api-endpoint: https://api.github.com/
+    hostname: github.com
+  dependencies:
+  existing-pull-requests: []
+  updating-a-pull-request: false
+  lockfile-only: false
+  update-subdependencies: false
+  ignore-conditions: []
+  requirements-update-strategy:
+  allowed-updates:
+  - dependency-type: direct
+    update-type: all
+  credentials-metadata:
+  - type: git_source
+    host: github.com
+  security-advisories: []
+  max-updater-run-time: 2700
+  vendor-dependencies: false
+  experiments:
+    grouped-updates-prototype: true
+  reject-external-code: false
+  commit-message-options:
+    prefix:
+    prefix-development:
+    include-scope:
+  security-updates-only: false
+  dependency-groups:
+  - name: my-group
+    rules:
+      patterns:
+        - "dummy-pkg-*"
+  - name: my-overlapping-group
+    rules:
+      patterns:
+        - "dummy-pkg-*"