Create separate PRs for any higher semver outside groups

common/lib/dependabot/dependency_group.rb

@@ -45,6 +45,12 @@ def ignored_versions_for(dependency)
       @ignore_condition.ignored_versions(dependency, SECURITY_UPDATES_ONLY)
     end
 
+    def targets_highest_versions_possible?
+      return true unless experimental_rules_enabled?
+
+      highest_semver_allowed == SEMVER_MAJOR
+    end
+
     def to_h
       { "name" => name }
     end
@@ -84,10 +90,13 @@ def pattern_rules?
       rules.key?("patterns") && rules["patterns"]&.any?
     end
 
+    def highest_semver_allowed
+      rules.fetch("highest-semver-allowed", DEFAULT_SEMVER_LEVEL)
+    end
+
     def generate_ignore_condition!
       return NullIgnoreCondition.new unless experimental_rules_enabled?
 
-      highest_semver_allowed = rules.fetch("highest-semver-allowed", DEFAULT_SEMVER_LEVEL)
       ignored_update_types = case highest_semver_allowed
       when SEMVER_MAJOR
         []

updater/lib/dependabot/dependency_group_engine.rb

@@ -56,6 +56,25 @@ def assign_to_groups!(dependencies:)
       @groups_calculated = true
     end
 
+    # TODO: Limit the dependency set to those we know have passed-over updates
+    #
+    # This will make a second update attempt on every dependency in any groups
+    # which do not permit highest version avaliable upgrades.
+    #
+    # We can be smarter about this since the versions available will need
+    # to be checked at least once prior to this set being evaluated.
+    #
+    # It will require us to start evaluating the DependencyGroup inside the
+    # UpdaterChecker and expose methods for the highest resolvable version
+    # both with and without the group's ignore rules.
+    #
+    # I'd rather ship this change separately once we've proved this run schema
+    # works as expected in terms of creating both group and single PRs which do
+    # not interfere with each other.
+    def dependencies_with_ungrouped_semvar_levels
+      dependency_groups.reject(&:targets_highest_versions_possible?).map(&:dependencies).flatten
+    end
+
     private
 
     def initialize(dependency_groups:)

updater/lib/dependabot/dependency_snapshot.rb

@@ -73,7 +73,8 @@ def ungrouped_dependencies
       # If no groups are defined, all dependencies are ungrouped by default.
       return allowed_dependencies unless groups.any?
 
-      @dependency_group_engine.ungrouped_dependencies
+      @dependency_group_engine.ungrouped_dependencies +
+        @dependency_group_engine.dependencies_with_ungrouped_semvar_levels
     end
 
     private

updater/spec/dependabot/updater/operations/group_update_all_versions_spec.rb

@@ -271,41 +271,52 @@
       original_bundler_files(fixture: "bundler_grouped_by_types")
     end
 
-    it "creates a group PR for minor- and patch-level changes and individual PRs for major-level changes" do
-      # We should create a group PR with the latest minor versions for rack and rubocop
-      expect(mock_service).to receive(:create_pull_request) do |dependency_change|
-        expect(dependency_change.dependency_group.name).to eql("small-bumps")
-
-        # We updated the right dependencies
-        expect(dependency_change.updated_dependencies.map(&:name)).to eql(%w(rack rubocop))
-
-        # We've updated the gemfiles properly
-        gemfile = dependency_change.updated_dependency_files.find do |file|
-          file.path == "/Gemfile"
-        end
-        expect(gemfile.content).to eql(fixture("bundler_grouped_by_types/updated_minor_and_patch/Gemfile"))
+    let(:updated_group_dependency_files) do
+      bundler_files_for(fixture: "bundler_grouped_by_types", state: "updated_minor_and_patch")
+    end
 
-        gemfile_lock = dependency_change.updated_dependency_files.find do |file|
-          file.path == "/Gemfile.lock"
-        end
-        expect(gemfile_lock.content).to eql(fixture("bundler_grouped_by_types/updated_minor_and_patch/Gemfile.lock"))
-      end
+    let(:updated_rack_major_files) do
+      bundler_files_for(fixture: "bundler_grouped_by_types", state: "updated_rack_major")
+    end
 
-      # We should also create isolated PRs for their major versions
-      # expect(mock_service).to receive(:create_pull_request) do |dependency_change|
-      #   expect(dependency_change.dependency_group).to be_nil
+    let(:updated_rubocop_major_files) do
+      bundler_files_for(fixture: "bundler_grouped_by_types", state: "updated_rubocop_major")
+    end
 
-      #   # We updated the right dependencies
-      #   expect(dependency_change.updated_dependencies.map(&:name)).to eql(%w(rack))
-      # end
+    it "creates a group PR for minor- and patch-level changes and individual PRs for major-level changes" do
+      expect(mock_service).to receive(:create_pull_request).with(
+        an_object_having_attributes(
+          dependency_group: an_object_having_attributes(name: "small-bumps"),
+          updated_dependencies: [
+            an_object_having_attributes(name: "rack", version: "2.2.7", previous_version: "2.1.4.3"),
+            an_object_having_attributes(name: "rubocop", version: "0.93.1", previous_version: "0.76.0")
+          ],
+          updated_dependency_files: updated_group_dependency_files
+        ),
+        "mock-sha"
+      )
 
-      # We should also create isolated PRs for their major versions
-      # expect(mock_service).to receive(:create_pull_request) do |dependency_change|
-      #   expect(dependency_change.dependency_group).to be_nil
+      expect(mock_service).to receive(:create_pull_request).with(
+        an_object_having_attributes(
+          dependency_group: nil,
+          updated_dependencies: [
+            an_object_having_attributes(name: "rack", version: "3.0.8", previous_version: "2.1.4.3")
+          ],
+          updated_dependency_files: updated_rack_major_files
+        ),
+        "mock-sha"
+      )
 
-      #   # We updated the right dependencies
-      #   expect(dependency_change.updated_dependencies.map(&:name)).to eql(%w(rubocop))
-      # end
+      expect(mock_service).to receive(:create_pull_request).with(
+        an_object_having_attributes(
+          dependency_group: nil,
+          updated_dependencies: [
+            an_object_having_attributes(name: "rubocop", version: "1.54.2", previous_version: "0.76.0")
+          ],
+          updated_dependency_files: updated_rubocop_major_files
+        ),
+        "mock-sha"
+      )
 
       group_update_all.perform
     end

updater/spec/fixtures/bundler_grouped_by_types/updated_rack_major/Gemfile

@@ -0,0 +1,10 @@
+# frozen_string_literal: true
+
+source "https://rubygems.org"
+
+gem "rack", "~> 3.0.8"
+gem "toml-rb", "~> 2.2.0"
+
+group :development do
+  gem "rubocop", "~> 0.76.0"
+end

updater/spec/fixtures/bundler_grouped_by_types/updated_rack_major/Gemfile.lock

@@ -0,0 +1,35 @@
+GEM
+  remote: https://rubygems.org/
+  specs:
+    ast (2.4.2)
+    citrus (3.0.2)
+    jaro_winkler (1.5.6)
+    parallel (1.23.0)
+    parser (3.2.2.3)
+      ast (~> 2.4.1)
+      racc
+    racc (1.7.1)
+    rack (3.0.8)
+    rainbow (3.1.1)
+    rubocop (0.76.0)
+      jaro_winkler (~> 1.5.1)
+      parallel (~> 1.10)
+      parser (>= 2.6)
+      rainbow (>= 2.2.2, < 4.0)
+      ruby-progressbar (~> 1.7)
+      unicode-display_width (>= 1.4.0, < 1.7)
+    ruby-progressbar (1.13.0)
+    toml-rb (2.2.0)
+      citrus (~> 3.0, > 3.0)
+    unicode-display_width (1.6.1)
+
+PLATFORMS
+  ruby
+
+DEPENDENCIES
+  rack (~> 3.0.8)
+  rubocop (~> 0.76.0)
+  toml-rb (~> 2.2.0)
+
+BUNDLED WITH
+   1.14.6

updater/spec/fixtures/bundler_grouped_by_types/updated_rubocop_major/Gemfile

@@ -0,0 +1,10 @@
+# frozen_string_literal: true
+
+source "https://rubygems.org"
+
+gem "rack", "~> 2.1.4"
+gem "toml-rb", "~> 2.2.0"
+
+group :development do
+  gem "rubocop", "~> 1.54.2"
+end

updater/spec/fixtures/bundler_grouped_by_types/updated_rubocop_major/Gemfile.lock

@@ -0,0 +1,44 @@
+GEM
+  remote: https://rubygems.org/
+  specs:
+    ast (2.4.2)
+    citrus (3.0.2)
+    json (2.6.3)
+    language_server-protocol (3.17.0.3)
+    parallel (1.23.0)
+    parser (3.2.2.3)
+      ast (~> 2.4.1)
+      racc
+    racc (1.7.1)
+    rack (2.1.4.3)
+    rainbow (3.1.1)
+    regexp_parser (2.8.1)
+    rexml (3.2.5)
+    rubocop (1.54.2)
+      json (~> 2.3)
+      language_server-protocol (>= 3.17.0)
+      parallel (~> 1.10)
+      parser (>= 3.2.2.3)
+      rainbow (>= 2.2.2, < 4.0)
+      regexp_parser (>= 1.8, < 3.0)
+      rexml (>= 3.2.5, < 4.0)
+      rubocop-ast (>= 1.28.0, < 2.0)
+      ruby-progressbar (~> 1.7)
+      unicode-display_width (>= 2.4.0, < 3.0)
+    rubocop-ast (1.29.0)
+      parser (>= 3.2.1.0)
+    ruby-progressbar (1.13.0)
+    toml-rb (2.2.0)
+      citrus (~> 3.0, > 3.0)
+    unicode-display_width (2.4.2)
+
+PLATFORMS
+  ruby
+
+DEPENDENCIES
+  rack (~> 2.1.4)
+  rubocop (~> 1.54.2)
+  toml-rb (~> 2.2.0)
+
+BUNDLED WITH
+   1.14.6