diff --git a/bundler/lib/dependabot/bundler/update_checker/force_updater.rb b/bundler/lib/dependabot/bundler/update_checker/force_updater.rb
index c14558c41d9..686beaed4eb 100644
--- a/bundler/lib/dependabot/bundler/update_checker/force_updater.rb
+++ b/bundler/lib/dependabot/bundler/update_checker/force_updater.rb
@@ -77,6 +77,15 @@ def original_dependencies
             ).parse
         end
 
+        def top_level_dependencies
+          @top_level_dependencies ||=
+            FileParser.new(
+              dependency_files: dependency_files.reject { |file| file.name == lockfile.name },
+              credentials: credentials,
+              source: nil
+            ).parse
+        end
+
         def dependencies_from(updated_deps, specs)
           # You might think we'd want to remove dependencies whose version
           # hadn't changed from this array. We don't. We still need to unlock
@@ -85,14 +94,17 @@ def dependencies_from(updated_deps, specs)
           #
           # This is kind of a bug in Bundler, and we should try to fix it,
           # but resolving it won't necessarily be easy.
-          updated_deps.filter_map do |dep|
-            original_dep =
-              original_dependencies.find { |d| d.name == dep.fetch("name") }
-            spec = specs.find { |d| d.fetch("name") == dep.fetch("name") }
 
-            next if spec.fetch("version") == original_dep.version
+          # put the lead dependency first
+          index = specs.index { |dep| dep["name"] == updated_deps.first["name"] }
+          specs.unshift(specs.delete_at(index))
+          specs.filter_map do |dep|
+            next unless top_level_dependencies.find { |d| d.name == dep.fetch("name") }
+
+            original_dep = original_dependencies.find { |d| d.name == dep.fetch("name") }
+            next if dep.fetch("version") == original_dep.version
 
-            build_dependency(original_dep, spec)
+            build_dependency(original_dep, dep)
           end
         end
 
diff --git a/bundler/spec/dependabot/bundler/update_checker/force_updater_spec.rb b/bundler/spec/dependabot/bundler/update_checker/force_updater_spec.rb
index 1c0fd2ff978..653251dfb83 100644
--- a/bundler/spec/dependabot/bundler/update_checker/force_updater_spec.rb
+++ b/bundler/spec/dependabot/bundler/update_checker/force_updater_spec.rb
@@ -215,5 +215,50 @@
           to raise_error(Dependabot::DependencyFileNotResolvable)
       end
     end
+
+    context "when peer dependencies in the Gemfile should update together" do
+      let(:dependency_files) { bundler_project_dependency_files("top_level_update") }
+      let(:target_version) { "19.4" }
+      let(:dependency_name) { "octicons" }
+      let(:requirements) do
+        [{
+          file: "Gemfile",
+          requirement: "~> 19.2",
+          groups: [:default],
+          source: nil
+        }]
+      end
+      let(:expected_requirements) do
+        [{
+          file: "Gemfile",
+          requirement: "~> 19.4",
+          groups: [:default],
+          source: nil
+        }]
+      end
+
+      it "updates all dependencies" do
+        expect(updated_dependencies).to eq(
+          [
+            Dependabot::Dependency.new(
+              name: "octicons",
+              version: "19.4.0",
+              previous_version: "19.2.0",
+              requirements: expected_requirements,
+              previous_requirements: requirements,
+              package_manager: "bundler"
+            ),
+            Dependabot::Dependency.new(
+              name: "octicons_helper",
+              version: "19.4.0",
+              previous_version: "19.2.0",
+              requirements: expected_requirements,
+              previous_requirements: requirements,
+              package_manager: "bundler"
+            )
+          ]
+        )
+      end
+    end
   end
 end
diff --git a/bundler/spec/fixtures/projects/bundler1/top_level_update/Gemfile b/bundler/spec/fixtures/projects/bundler1/top_level_update/Gemfile
new file mode 100644
index 00000000000..3a4d403c749
--- /dev/null
+++ b/bundler/spec/fixtures/projects/bundler1/top_level_update/Gemfile
@@ -0,0 +1,8 @@
+# frozen_string_literal: true
+
+source "https://rubygems.org"
+
+git_source(:github) {|repo_name| "https://github.com/#{repo_name}" }
+
+gem "octicons", "~> 19.2"
+gem "octicons_helper", "~> 19.2"
diff --git a/bundler/spec/fixtures/projects/bundler1/top_level_update/Gemfile.lock b/bundler/spec/fixtures/projects/bundler1/top_level_update/Gemfile.lock
new file mode 100644
index 00000000000..dda2e5040f3
--- /dev/null
+++ b/bundler/spec/fixtures/projects/bundler1/top_level_update/Gemfile.lock
@@ -0,0 +1,74 @@
+GEM
+  remote: https://rubygems.org/
+  specs:
+    actionpack (7.0.6)
+      actionview (= 7.0.6)
+      activesupport (= 7.0.6)
+      rack (~> 2.0, >= 2.2.4)
+      rack-test (>= 0.6.3)
+      rails-dom-testing (~> 2.0)
+      rails-html-sanitizer (~> 1.0, >= 1.2.0)
+    actionview (7.0.6)
+      activesupport (= 7.0.6)
+      builder (~> 3.1)
+      erubi (~> 1.4)
+      rails-dom-testing (~> 2.0)
+      rails-html-sanitizer (~> 1.1, >= 1.2.0)
+    activesupport (7.0.6)
+      concurrent-ruby (~> 1.0, >= 1.0.2)
+      i18n (>= 1.6, < 2)
+      minitest (>= 5.1)
+      tzinfo (~> 2.0)
+    builder (3.2.4)
+    concurrent-ruby (1.2.2)
+    crass (1.0.6)
+    erubi (1.12.0)
+    i18n (1.14.1)
+      concurrent-ruby (~> 1.0)
+    loofah (2.21.3)
+      crass (~> 1.0.2)
+      nokogiri (>= 1.12.0)
+    method_source (1.0.0)
+    mini_portile2 (2.8.4)
+    minitest (5.18.1)
+    nokogiri (1.15.3)
+      mini_portile2 (~> 2.8.2)
+      racc (~> 1.4)
+    octicons (19.2.0)
+    octicons_helper (19.2.0)
+      actionview
+      octicons (= 19.2.0)
+      railties
+    racc (1.7.1)
+    rack (2.2.7)
+    rack-test (2.1.0)
+      rack (>= 1.3)
+    rails-dom-testing (2.1.1)
+      activesupport (>= 5.0.0)
+      minitest
+      nokogiri (>= 1.6)
+    rails-html-sanitizer (1.6.0)
+      loofah (~> 2.21)
+      nokogiri (~> 1.14)
+    railties (7.0.6)
+      actionpack (= 7.0.6)
+      activesupport (= 7.0.6)
+      method_source
+      rake (>= 12.2)
+      thor (~> 1.0)
+      zeitwerk (~> 2.5)
+    rake (13.0.6)
+    thor (1.2.2)
+    tzinfo (2.0.6)
+      concurrent-ruby (~> 1.0)
+    zeitwerk (2.6.8)
+
+PLATFORMS
+  ruby
+
+DEPENDENCIES
+  octicons (~> 19.2)
+  octicons_helper (~> 19.2)
+
+BUNDLED WITH
+   1.17.3
diff --git a/bundler/spec/fixtures/projects/bundler2/top_level_update/Gemfile b/bundler/spec/fixtures/projects/bundler2/top_level_update/Gemfile
new file mode 100644
index 00000000000..3a4d403c749
--- /dev/null
+++ b/bundler/spec/fixtures/projects/bundler2/top_level_update/Gemfile
@@ -0,0 +1,8 @@
+# frozen_string_literal: true
+
+source "https://rubygems.org"
+
+git_source(:github) {|repo_name| "https://github.com/#{repo_name}" }
+
+gem "octicons", "~> 19.2"
+gem "octicons_helper", "~> 19.2"
diff --git a/bundler/spec/fixtures/projects/bundler2/top_level_update/Gemfile.lock b/bundler/spec/fixtures/projects/bundler2/top_level_update/Gemfile.lock
new file mode 100644
index 00000000000..fc0126ffccd
--- /dev/null
+++ b/bundler/spec/fixtures/projects/bundler2/top_level_update/Gemfile.lock
@@ -0,0 +1,74 @@
+GEM
+  remote: https://rubygems.org/
+  specs:
+    actionpack (7.0.6)
+      actionview (= 7.0.6)
+      activesupport (= 7.0.6)
+      rack (~> 2.0, >= 2.2.4)
+      rack-test (>= 0.6.3)
+      rails-dom-testing (~> 2.0)
+      rails-html-sanitizer (~> 1.0, >= 1.2.0)
+    actionview (7.0.6)
+      activesupport (= 7.0.6)
+      builder (~> 3.1)
+      erubi (~> 1.4)
+      rails-dom-testing (~> 2.0)
+      rails-html-sanitizer (~> 1.1, >= 1.2.0)
+    activesupport (7.0.6)
+      concurrent-ruby (~> 1.0, >= 1.0.2)
+      i18n (>= 1.6, < 2)
+      minitest (>= 5.1)
+      tzinfo (~> 2.0)
+    builder (3.2.4)
+    concurrent-ruby (1.2.2)
+    crass (1.0.6)
+    erubi (1.12.0)
+    i18n (1.14.1)
+      concurrent-ruby (~> 1.0)
+    loofah (2.21.3)
+      crass (~> 1.0.2)
+      nokogiri (>= 1.12.0)
+    method_source (1.0.0)
+    mini_portile2 (2.8.2)
+    minitest (5.18.1)
+    nokogiri (1.15.2)
+      mini_portile2 (~> 2.8.2)
+      racc (~> 1.4)
+    octicons (19.2.0)
+    octicons_helper (19.2.0)
+      actionview
+      octicons (= 19.2.0)
+      railties
+    racc (1.7.1)
+    rack (2.2.7)
+    rack-test (2.1.0)
+      rack (>= 1.3)
+    rails-dom-testing (2.1.1)
+      activesupport (>= 5.0.0)
+      minitest
+      nokogiri (>= 1.6)
+    rails-html-sanitizer (1.6.0)
+      loofah (~> 2.21)
+      nokogiri (~> 1.14)
+    railties (7.0.6)
+      actionpack (= 7.0.6)
+      activesupport (= 7.0.6)
+      method_source
+      rake (>= 12.2)
+      thor (~> 1.0)
+      zeitwerk (~> 2.5)
+    rake (13.0.6)
+    thor (1.2.2)
+    tzinfo (2.0.6)
+      concurrent-ruby (~> 1.0)
+    zeitwerk (2.6.8)
+
+PLATFORMS
+  ruby
+
+DEPENDENCIES
+  octicons (~> 19.2)
+  octicons_helper (~> 19.2)
+
+BUNDLED WITH
+   2.1.4