diff --git a/Library/Homebrew/test/cask/cmd/upgrade_spec.rb b/Library/Homebrew/test/cask/cmd/upgrade_spec.rb
index ee7b9c8713..476364c7c6 100644
--- a/Library/Homebrew/test/cask/cmd/upgrade_spec.rb
+++ b/Library/Homebrew/test/cask/cmd/upgrade_spec.rb
@@ -74,6 +74,54 @@ describe Cask::Cmd::Upgrade, :cask do
     end
 
     describe "with --greedy it checks additional Casks" do
+      it 'includes the Casks with "auto_updates true" or "version latest"' do
+        local_caffeine = Cask::CaskLoader.load("local-caffeine")
+        local_caffeine_path = Cask::Config.global.appdir.join("Caffeine.app")
+        auto_updates = Cask::CaskLoader.load("auto-updates")
+        auto_updates_path = Cask::Config.global.appdir.join("MyFancyApp.app")
+        local_transmission = Cask::CaskLoader.load("local-transmission")
+        local_transmission_path = Cask::Config.global.appdir.join("Transmission.app")
+        version_latest = Cask::CaskLoader.load("version-latest")
+        version_latest_path_1 = Cask::Config.global.appdir.join("Caffeine Mini.app")
+        version_latest_path_2 = Cask::Config.global.appdir.join("Caffeine Pro.app")
+
+        expect(local_caffeine).to be_installed
+        expect(local_caffeine_path).to be_a_directory
+        expect(local_caffeine.versions).to include("1.2.2")
+
+        expect(auto_updates).to be_installed
+        expect(auto_updates_path).to be_a_directory
+        expect(auto_updates.versions).to include("2.57")
+
+        expect(local_transmission).to be_installed
+        expect(local_transmission_path).to be_a_directory
+        expect(local_transmission.versions).to include("2.60")
+
+        expect(version_latest).to be_installed
+        expect(version_latest_path_1).to be_a_directory
+        expect(version_latest_path_2).to be_a_directory
+        expect(version_latest.versions).to include("latest")
+
+        described_class.run("--greedy")
+
+        expect(local_caffeine).to be_installed
+        expect(local_caffeine_path).to be_a_directory
+        expect(local_caffeine.versions).to include("1.2.3")
+
+        expect(auto_updates).to be_installed
+        expect(auto_updates_path).to be_a_directory
+        expect(auto_updates.versions).to include("2.61")
+
+        expect(local_transmission).to be_installed
+        expect(local_transmission_path).to be_a_directory
+        expect(local_transmission.versions).to include("2.61")
+
+        expect(version_latest).to be_installed
+        expect(version_latest_path_1).to be_a_directory
+        expect(version_latest_path_2).to be_a_directory
+        expect(version_latest.versions).to include("latest")
+      end
+
       it 'does not include the Casks with "auto_updates true" when the version did not change' do
         cask = Cask::CaskLoader.load("auto-updates")
         cask_path = cask.config.appdir.join("MyFancyApp.app")