diff --git a/bundler/spec/dependabot/bundler/update_checker_spec.rb b/bundler/spec/dependabot/bundler/update_checker_spec.rb
index fb2c15887e3..f3ea1414341 100644
--- a/bundler/spec/dependabot/bundler/update_checker_spec.rb
+++ b/bundler/spec/dependabot/bundler/update_checker_spec.rb
@@ -363,6 +363,36 @@
         end
       end
     end
+
+    context "for a gem that depends on bundler" do
+      let(:dependenc_files) { bundler_project_dependency_files("guard_bundler") }
+
+      before do
+        rubygems_response = fixture("ruby", "rubygems_response_guard_bundler.json")
+        stub_request(:get, rubygems_url + "versions/guard-bundler.json").
+          to_return(status: 200, body: rubygems_response)
+      end
+
+      let(:dependency_name) { "guard-bundler" }
+      let(:current_version) { "2.2.1" }
+      let(:requirements) do
+        [{
+          file: "Gemfile",
+          requirement: "~> 2.2.1",
+          groups: [],
+          source: nil
+        }]
+      end
+
+      context "bundler v1", :bundler_v1_only do
+        # Surprisingly, this returns the incompatible version 3.0.0.
+        xit { is_expected.to eq(Gem::Version.new("2.2.1")) }
+      end
+
+      context "bundler v2", :bundler_v2_only do
+        it { is_expected.to eq(Gem::Version.new("3.0.0")) }
+      end
+    end
   end
 
   describe "#lowest_security_fix_version" do
diff --git a/bundler/spec/fixtures/ruby/rubygems_response_guard_bundler.json b/bundler/spec/fixtures/ruby/rubygems_response_guard_bundler.json
new file mode 100644
index 00000000000..79bc89d89c5
--- /dev/null
+++ b/bundler/spec/fixtures/ruby/rubygems_response_guard_bundler.json
@@ -0,0 +1 @@
+[{"authors":"Yann Lugrin","built_at":"2019-12-23T00:00:00.000Z","created_at":"2019-12-23T16:51:50.100Z","description":"Guard::Bundler automatically install/update your gem bundle when needed","downloads_count":138888,"metadata":{},"number":"3.0.0","summary":"Guard gem for Bundler","platform":"ruby","rubygems_version":"\u003e= 0","ruby_version":"\u003e= 2.4.9","prerelease":false,"licenses":["MIT"],"requirements":[],"sha":"c59d0bf0f65e6f800e4bbeb26b89a7b45cd4f17c170d67c50a8f3a097446ce9c"},{"authors":"Yann Lugrin","built_at":"2019-01-16T00:00:00.000Z","created_at":"2019-01-16T07:30:43.466Z","description":"Guard::Bundler automatically install/update your gem bundle when needed","downloads_count":1353682,"metadata":{},"number":"2.2.1","summary":"Guard gem for Bundler","platform":"ruby","rubygems_version":"\u003e= 0","ruby_version":"\u003e= 1.9.2","prerelease":false,"licenses":["MIT"],"requirements":[],"sha":"c2f8ad69d7c38775f0e60ff3a8a97df3e1b925a51553916fcd97f8c391435152"},{"authors":"Yann Lugrin","built_at":"2019-01-10T00:00:00.000Z","created_at":"2019-01-10T14:12:15.900Z","description":"Guard::Bundler automatically install/update your gem bundle when needed","downloads_count":23197,"metadata":{},"number":"2.2.0","summary":"Guard gem for Bundler","platform":"ruby","rubygems_version":"\u003e= 0","ruby_version":"\u003e= 1.9.2","prerelease":false,"licenses":["MIT"],"requirements":[],"sha":"db3494f840dd924a13a4f2f79ee67eef92b5555ab155cf33cbb278777a8b0d25"},{"authors":"Yann Lugrin","built_at":"2014-12-11T00:00:00.000Z","created_at":"2014-12-11T06:27:24.372Z","description":"Guard::Bundler automatically install/update your gem bundle when needed","downloads_count":2531228,"metadata":{},"number":"2.1.0","summary":"Guard gem for Bundler","platform":"ruby","rubygems_version":"\u003e= 0","ruby_version":"\u003e= 1.9.2","prerelease":false,"licenses":["MIT"],"requirements":[],"sha":"e0a1f96893866677ecf4238f524ca11602f70592afd0fb83d02df09867073898"},{"authors":"Yann Lugrin","built_at":"2013-10-30T00:00:00.000Z","created_at":"2013-10-30T11:00:19.545Z","description":"Guard::Bundler automatically install/update your gem bundle when needed","downloads_count":462401,"metadata":{},"number":"2.0.0","summary":"Guard gem for Bundler","platform":"ruby","rubygems_version":"\u003e= 0","ruby_version":"\u003e= 1.9.2","prerelease":false,"licenses":["MIT"],"requirements":[],"sha":"533a74e1002ea461b8a44c1a66f7783b4d9967bacc2d34342975246180bdebd7"},{"authors":"Yann Lugrin","built_at":"2012-06-15T00:00:00.000Z","created_at":"2012-06-15T09:22:13.404Z","description":"Guard::Bundler automatically install/update your gem bundle when needed","downloads_count":762953,"metadata":{},"number":"1.0.0","summary":"Guard gem for Bundler","platform":"ruby","rubygems_version":"\u003e= 1.3.6","ruby_version":null,"prerelease":false,"licenses":null,"requirements":null,"sha":"1ace3f43d27368b72f403226828dd6f4b1069cb25794800ea6d8afe4ad317869"},{"authors":"Yann Lugrin","built_at":"2011-05-13T22:00:00.000Z","created_at":"2011-05-14T14:01:16.218Z","description":"Guard::Bundler automatically install/update your gem bundle when needed","downloads_count":169520,"metadata":{},"number":"0.1.3","summary":"Guard gem for Bundler","platform":"ruby","rubygems_version":"\u003e= 1.3.6","ruby_version":null,"prerelease":false,"licenses":null,"requirements":null,"sha":"34e1fddfdcb3315eb99ce7bed8fb1b9cb3e722c8de196a91c4ad6948ed4aca13"},{"authors":"Yann Lugrin","built_at":"2011-02-17T23:00:00.000Z","created_at":"2011-02-18T12:44:59.013Z","description":"Guard::Bundler automatically install/update your gem bundle when needed","downloads_count":10477,"metadata":{},"number":"0.1.2","summary":"Guard gem for Bundler","platform":"ruby","rubygems_version":"\u003e= 1.3.6","ruby_version":null,"prerelease":false,"licenses":null,"requirements":null,"sha":"bb53cf08f60f587fcf9eb0a119046556e48e259ca5cf557ab98f4e1e701973f8"},{"authors":"Yann Lugrin","built_at":"2010-10-26T22:00:00.000Z","created_at":"2010-10-27T10:18:03.430Z","description":"Guard::Bundler automatically install/update your gem bundle when needed","downloads_count":3608,"metadata":{},"number":"0.1.1","summary":"Guard gem for Bundler","platform":"ruby","rubygems_version":"\u003e= 1.3.6","ruby_version":null,"prerelease":false,"licenses":null,"requirements":null,"sha":"4823bccaa8c62eaaed60a1d654a554893a9ca616d48fe447c0489c03136b8b69"},{"authors":"Yann Lugrin","built_at":"2010-10-23T22:00:00.000Z","created_at":"2010-10-24T12:11:15.715Z","description":"Guard::Bundler automatically install/update your gem bundle when needed","downloads_count":2880,"metadata":{},"number":"0.1.0","summary":"Guard gem for Bundler","platform":"ruby","rubygems_version":"\u003e= 1.3.6","ruby_version":null,"prerelease":false,"licenses":null,"requirements":null,"sha":"1f3d254b9ad6f6a71a60a9d22e43b6316aa5421c31300ec72cdd84f5f58c6519"}]
\ No newline at end of file