diff --git a/Library/Homebrew/cask/lib/hbc/artifact/moved.rb b/Library/Homebrew/cask/lib/hbc/artifact/moved.rb
index 11e019af2c..f5ef790ebb 100644
--- a/Library/Homebrew/cask/lib/hbc/artifact/moved.rb
+++ b/Library/Homebrew/cask/lib/hbc/artifact/moved.rb
@@ -70,8 +70,6 @@ module Hbc
         else
           command.run("/bin/mv", args: [target, source], sudo: true)
         end
-
-        add_altname_metadata(target, source.basename, command: command)
       end
 
       def delete(target, force: false, command: nil, **_)
diff --git a/Library/Homebrew/cask/lib/hbc/cli/upgrade.rb b/Library/Homebrew/cask/lib/hbc/cli/upgrade.rb
index bd80ad6905..808b64c4b7 100644
--- a/Library/Homebrew/cask/lib/hbc/cli/upgrade.rb
+++ b/Library/Homebrew/cask/lib/hbc/cli/upgrade.rb
@@ -55,14 +55,14 @@ module Hbc
 
             new_cask_installer.fetch
 
-            new_cask_installer.stage
-
             # Move the old Cask's artifacts back to staging
             old_cask_installer.start_upgrade
             # And flag it so in case of error
             started_upgrade = true
 
             # Install the new Cask
+            new_cask_installer.stage
+
             new_cask_installer.install_artifacts
             new_artifacts_installed = true
 
diff --git a/Library/Homebrew/cask/lib/hbc/installer.rb b/Library/Homebrew/cask/lib/hbc/installer.rb
index b2087e643d..8520f154db 100644
--- a/Library/Homebrew/cask/lib/hbc/installer.rb
+++ b/Library/Homebrew/cask/lib/hbc/installer.rb
@@ -360,16 +360,33 @@ module Hbc
 
       disable_accessibility_access
       uninstall_artifacts
+      backup
+    end
+
+    def backup
+      @cask.staged_path.rename backup_path
+      @cask.metadata_versioned_path.rename backup_metadata_path
+    end
+
+    def restore_backup
+      return unless backup_path.directory? && backup_metadata_path.directory?
+
+      Pathname.new(@cask.staged_path).rmtree if @cask.staged_path.exist?
+      Pathname.new(@cask.metadata_versioned_path).rmtree if @cask.metadata_versioned_path.exist?
+
+      backup_path.rename @cask.staged_path
+      backup_metadata_path.rename @cask.metadata_versioned_path
     end
 
     def revert_upgrade
       opoo "Reverting upgrade for Cask #{@cask}"
+      restore_backup
       install_artifacts
       enable_accessibility_access
     end
 
     def finalize_upgrade
-      purge_versioned_files
+      purge_backed_up_versioned_files
 
       puts summary
     end
@@ -402,10 +419,37 @@ module Hbc
       purge_caskroom_path
     end
 
+    def backup_path
+      return nil if @cask.staged_path.nil?
+      Pathname.new "#{@cask.staged_path}.upgrading"
+    end
+
+    def backup_metadata_path
+      return nil if @cask.metadata_versioned_path.nil?
+      Pathname.new "#{@cask.metadata_versioned_path}.upgrading"
+    end
+
     def gain_permissions_remove(path)
       Utils.gain_permissions_remove(path, command: @command)
     end
 
+    def purge_backed_up_versioned_files
+      ohai "Purging files for version #{@cask.version} of Cask #{@cask}"
+
+      # versioned staged distribution
+      gain_permissions_remove(backup_path) if !backup_path.nil? && backup_path.exist?
+
+      # Homebrew-Cask metadata
+      if backup_metadata_path.directory?
+        backup_metadata_path.children.each do |subdir|
+          unless PERSISTENT_METADATA_SUBDIRS.include?(subdir.basename)
+            gain_permissions_remove(subdir)
+          end
+        end
+      end
+      backup_metadata_path.rmdir_if_possible
+    end
+
     def purge_versioned_files
       ohai "Purging files for version #{@cask.version} of Cask #{@cask}"
 
diff --git a/Library/Homebrew/test/cask/cli/upgrade_spec.rb b/Library/Homebrew/test/cask/cli/upgrade_spec.rb
index 5f389d6950..49775156e6 100644
--- a/Library/Homebrew/test/cask/cli/upgrade_spec.rb
+++ b/Library/Homebrew/test/cask/cli/upgrade_spec.rb
@@ -9,6 +9,7 @@ describe Hbc::CLI::Upgrade, :cask do
         "outdated/local-caffeine",
         "outdated/local-transmission",
         "outdated/auto-updates",
+        "outdated/version-latest",
       ]
     }
 
@@ -103,6 +104,9 @@ describe Hbc::CLI::Upgrade, :cask do
         auto_updates_path = Hbc.appdir.join("MyFancyApp.app")
         local_transmission = Hbc::CaskLoader.load("local-transmission")
         local_transmission_path = Hbc.appdir.join("Transmission.app")
+        version_latest = Hbc::CaskLoader.load("version-latest")
+        version_latest_path_1 = Hbc.appdir.join("Caffeine Mini.app")
+        version_latest_path_2 = Hbc.appdir.join("Caffeine Pro.app")
 
         expect(local_caffeine).to be_installed
         expect(local_caffeine_path).to be_a_directory
@@ -116,6 +120,11 @@ describe Hbc::CLI::Upgrade, :cask do
         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
@@ -129,6 +138,11 @@ describe Hbc::CLI::Upgrade, :cask do
         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
diff --git a/Library/Homebrew/test/support/fixtures/cask/Casks/outdated/version-latest.rb b/Library/Homebrew/test/support/fixtures/cask/Casks/outdated/version-latest.rb
new file mode 100644
index 0000000000..2ac869f896
--- /dev/null
+++ b/Library/Homebrew/test/support/fixtures/cask/Casks/outdated/version-latest.rb
@@ -0,0 +1,10 @@
+cask 'version-latest' do
+  version :latest
+  sha256 :no_check
+
+  url "file://#{TEST_FIXTURE_DIR}/cask/caffeines.zip"
+  homepage 'http://example.com/local-caffeine'
+
+  app 'Caffeine Mini.app'
+  app 'Caffeine Pro.app'
+end
diff --git a/Library/Homebrew/test/support/fixtures/cask/Casks/version-latest.rb b/Library/Homebrew/test/support/fixtures/cask/Casks/version-latest.rb
new file mode 100644
index 0000000000..2ac869f896
--- /dev/null
+++ b/Library/Homebrew/test/support/fixtures/cask/Casks/version-latest.rb
@@ -0,0 +1,10 @@
+cask 'version-latest' do
+  version :latest
+  sha256 :no_check
+
+  url "file://#{TEST_FIXTURE_DIR}/cask/caffeines.zip"
+  homepage 'http://example.com/local-caffeine'
+
+  app 'Caffeine Mini.app'
+  app 'Caffeine Pro.app'
+end