diff --git a/Library/Homebrew/cask/lib/hbc/artifact/moved.rb b/Library/Homebrew/cask/lib/hbc/artifact/moved.rb
index ba1c8e9072003..11e019af2c4f7 100644
--- a/Library/Homebrew/cask/lib/hbc/artifact/moved.rb
+++ b/Library/Homebrew/cask/lib/hbc/artifact/moved.rb
@@ -12,7 +12,7 @@ def install_phase(**options)
       end
 
       def uninstall_phase(**options)
-        delete(**options)
+        move_back(**options)
       end
 
       def summarize_installed
@@ -30,7 +30,7 @@ def move(force: false, command: nil, **options)
           message = "It seems there is already #{self.class.english_article} #{self.class.english_name} at '#{target}'"
           raise CaskError, "#{message}." unless force
           opoo "#{message}; overwriting."
-          delete(force: force, command: command, **options)
+          delete(target, force: force, command: command, **options)
         end
 
         unless source.exist?
@@ -49,7 +49,32 @@ def move(force: false, command: nil, **options)
         add_altname_metadata(target, source.basename, command: command)
       end
 
-      def delete(force: false, command: nil, **_)
+      def move_back(skip: false, force: false, command: nil, **options)
+        if Utils.path_occupied?(source)
+          message = "It seems there is already #{self.class.english_article} #{self.class.english_name} at '#{source}'"
+          raise CaskError, "#{message}." unless force
+          opoo "#{message}; overwriting."
+          delete(source, force: force, command: command, **options)
+        end
+
+        unless target.exist?
+          return if skip
+          raise CaskError, "It seems the #{self.class.english_name} source '#{target}' is not there."
+        end
+
+        ohai "Moving #{self.class.english_name} '#{target.basename}' back to '#{source}'."
+        source.dirname.mkpath
+
+        if source.parent.writable?
+          FileUtils.move(target, source)
+        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, **_)
         ohai "Removing #{self.class.english_name} '#{target}'."
         raise CaskError, "Cannot remove undeletable #{self.class.english_name}." if MacOS.undeletable?(target)
 
diff --git a/Library/Homebrew/cask/lib/hbc/cli.rb b/Library/Homebrew/cask/lib/hbc/cli.rb
index e147c82809c61..215b59843dc73 100644
--- a/Library/Homebrew/cask/lib/hbc/cli.rb
+++ b/Library/Homebrew/cask/lib/hbc/cli.rb
@@ -21,6 +21,7 @@
 require "hbc/cli/search"
 require "hbc/cli/style"
 require "hbc/cli/uninstall"
+require "hbc/cli/upgrade"
 require "hbc/cli/--version"
 require "hbc/cli/zap"
 
diff --git a/Library/Homebrew/cask/lib/hbc/cli/upgrade.rb b/Library/Homebrew/cask/lib/hbc/cli/upgrade.rb
new file mode 100644
index 0000000000000..bd80ad6905d63
--- /dev/null
+++ b/Library/Homebrew/cask/lib/hbc/cli/upgrade.rb
@@ -0,0 +1,87 @@
+module Hbc
+  class CLI
+    class Upgrade < AbstractCommand
+      option "--greedy", :greedy, false
+      option "--quiet",  :quiet, false
+      option "--force", :force, false
+      option "--skip-cask-deps", :skip_cask_deps, false
+
+      def initialize(*)
+        super
+        self.verbose = ($stdout.tty? || verbose?) && !quiet?
+      end
+
+      def run
+        outdated_casks = casks(alternative: lambda {
+          Hbc.installed.select do |cask|
+            cask.outdated?(greedy?)
+          end
+        }).select { |cask| cask.outdated?(true) }
+
+        if outdated_casks.empty?
+          oh1 "No Casks to upgrade"
+          return
+        end
+
+        oh1 "Upgrading #{Formatter.pluralize(outdated_casks.length, "outdated package")}, with result:"
+        puts outdated_casks.map { |f| "#{f.full_name} #{f.version}" } * ", "
+
+        outdated_casks.each do |old_cask|
+          odebug "Started upgrade process for Cask #{old_cask}"
+          raise CaskNotInstalledError, old_cask unless old_cask.installed? || force?
+
+          raise CaskUnavailableError.new(old_cask, "The Caskfile is missing!") if old_cask.installed_caskfile.nil?
+
+          old_cask = CaskLoader.load(old_cask.installed_caskfile)
+
+          old_cask_installer = Installer.new(old_cask, binaries: binaries?, verbose: verbose?, force: force?, upgrade: true)
+
+          new_cask = CaskLoader.load(old_cask.to_s)
+
+          new_cask_installer =
+            Installer.new(new_cask, binaries:       binaries?,
+                                    verbose:        verbose?,
+                                    force:          force?,
+                                    skip_cask_deps: skip_cask_deps?,
+                                    require_sha:    require_sha?,
+                                    upgrade: true)
+
+          started_upgrade = false
+          new_artifacts_installed = false
+
+          begin
+            # Start new Cask's installation steps
+            new_cask_installer.check_conflicts
+
+            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.install_artifacts
+            new_artifacts_installed = true
+
+            new_cask_installer.enable_accessibility_access
+
+            # If successful, wipe the old Cask from staging
+            old_cask_installer.finalize_upgrade
+          rescue CaskError => e
+            new_cask_installer.uninstall_artifacts if new_artifacts_installed
+            new_cask_installer.purge_versioned_files
+            old_cask_installer.revert_upgrade if started_upgrade
+            raise e
+          end
+        end
+      end
+
+      def self.help
+        "upgrades all outdated casks"
+      end
+    end
+  end
+end
diff --git a/Library/Homebrew/cask/lib/hbc/installer.rb b/Library/Homebrew/cask/lib/hbc/installer.rb
index 1063f488bcf28..6056250fc05ce 100644
--- a/Library/Homebrew/cask/lib/hbc/installer.rb
+++ b/Library/Homebrew/cask/lib/hbc/installer.rb
@@ -19,7 +19,7 @@ class Installer
 
     PERSISTENT_METADATA_SUBDIRS = ["gpg"].freeze
 
-    def initialize(cask, command: SystemCommand, force: false, skip_cask_deps: false, binaries: true, verbose: false, require_sha: false)
+    def initialize(cask, command: SystemCommand, force: false, skip_cask_deps: false, binaries: true, verbose: false, require_sha: false, upgrade: false)
       @cask = cask
       @command = command
       @force = force
@@ -28,9 +28,10 @@ def initialize(cask, command: SystemCommand, force: false, skip_cask_deps: false
       @verbose = verbose
       @require_sha = require_sha
       @reinstall = false
+      @upgrade = upgrade
     end
 
-    attr_predicate :binaries?, :force?, :skip_cask_deps?, :require_sha?, :verbose?
+    attr_predicate :binaries?, :force?, :skip_cask_deps?, :require_sha?, :upgrade?, :verbose?
 
     def self.print_caveats(cask)
       odebug "Printing caveats"
@@ -82,7 +83,7 @@ def stage
     def install
       odebug "Hbc::Installer#install"
 
-      if @cask.installed? && !force? && !@reinstall
+      if @cask.installed? && !force? && !@reinstall && !upgrade?
         raise CaskAlreadyInstalledError, @cask
       end
 
@@ -129,13 +130,13 @@ def uninstall_existing_cask
       installed_cask = installed_caskfile.exist? ? CaskLoader.load(installed_caskfile) : @cask
 
       # Always force uninstallation, ignore method parameter
-      Installer.new(installed_cask, binaries: binaries?, verbose: verbose?, force: true).uninstall
+      Installer.new(installed_cask, binaries: binaries?, verbose: verbose?, force: true, upgrade: upgrade?).uninstall
     end
 
     def summary
       s = ""
       s << "#{Emoji.install_badge}  " if Emoji.enabled?
-      s << "#{@cask} was successfully installed!"
+      s << "#{@cask} was successfully #{upgrade? ? "upgraded" : "installed"}!"
     end
 
     def download
@@ -367,12 +368,31 @@ def save_caskfile
     def uninstall
       oh1 "Uninstalling Cask #{@cask}"
       disable_accessibility_access
-      uninstall_artifacts
+      uninstall_artifacts(clear: true)
       purge_versioned_files
       purge_caskroom_path if force?
     end
 
-    def uninstall_artifacts
+    def start_upgrade
+      oh1 "Starting upgrade for Cask #{@cask}"
+
+      disable_accessibility_access
+      uninstall_artifacts
+    end
+
+    def revert_upgrade
+      opoo "Reverting upgrade for Cask #{@cask}"
+      install_artifacts
+      enable_accessibility_access
+    end
+
+    def finalize_upgrade
+      purge_versioned_files
+
+      puts summary
+    end
+
+    def uninstall_artifacts(clear: false)
       odebug "Un-installing artifacts"
       artifacts = @cask.artifacts
 
@@ -381,7 +401,7 @@ def uninstall_artifacts
       artifacts.each do |artifact|
         next unless artifact.respond_to?(:uninstall_phase)
         odebug "Un-installing artifact of class #{artifact.class}"
-        artifact.uninstall_phase(command: @command, verbose: verbose?, force: force?)
+        artifact.uninstall_phase(command: @command, verbose: verbose?, skip: clear, force: force?)
       end
     end
 
@@ -405,7 +425,7 @@ def gain_permissions_remove(path)
     end
 
     def purge_versioned_files
-      odebug "Purging files for version #{@cask.version} of Cask #{@cask}"
+      ohai "Purging files for version #{@cask.version} of Cask #{@cask}"
 
       # versioned staged distribution
       gain_permissions_remove(@cask.staged_path) if !@cask.staged_path.nil? && @cask.staged_path.exist?
@@ -420,10 +440,10 @@ def purge_versioned_files
         end
       end
       @cask.metadata_versioned_path.rmdir_if_possible
-      @cask.metadata_master_container_path.rmdir_if_possible
+      @cask.metadata_master_container_path.rmdir_if_possible unless upgrade?
 
       # toplevel staged distribution
-      @cask.caskroom_path.rmdir_if_possible
+      @cask.caskroom_path.rmdir_if_possible unless upgrade?
     end
 
     def purge_caskroom_path
diff --git a/Library/Homebrew/test/cask/cli/reinstall_spec.rb b/Library/Homebrew/test/cask/cli/reinstall_spec.rb
index 5e551e5b5a2fb..3737a7a701357 100644
--- a/Library/Homebrew/test/cask/cli/reinstall_spec.rb
+++ b/Library/Homebrew/test/cask/cli/reinstall_spec.rb
@@ -13,7 +13,8 @@
       Already downloaded: .*local-caffeine--1.2.3.zip
       ==> Verifying checksum for Cask local-caffeine
       ==> Uninstalling Cask local-caffeine
-      ==> Removing App '.*Caffeine.app'.
+      ==> Moving App 'Caffeine.app' back to '.*Caffeine.app'.
+      ==> Purging files for version 1.2.3 of Cask local-caffeine
       ==> Installing Cask local-caffeine
       ==> Moving App 'Caffeine.app' to '.*Caffeine.app'.
       .*local-caffeine was successfully installed!
diff --git a/Library/Homebrew/test/cask/cli/uninstall_spec.rb b/Library/Homebrew/test/cask/cli/uninstall_spec.rb
index 1ab8f7e4da89a..345e1b9f230a6 100644
--- a/Library/Homebrew/test/cask/cli/uninstall_spec.rb
+++ b/Library/Homebrew/test/cask/cli/uninstall_spec.rb
@@ -12,7 +12,8 @@
 
     output = Regexp.new <<~EOS
       ==> Uninstalling Cask local-caffeine
-      ==> Removing App '.*Caffeine.app'.
+      ==> Moving App 'Caffeine.app' back to '.*Caffeine.app'.
+      ==> Purging files for version 1.2.3 of Cask local-caffeine
     EOS
 
     expect {
diff --git a/Library/Homebrew/test/cask/cli/upgrade_spec.rb b/Library/Homebrew/test/cask/cli/upgrade_spec.rb
new file mode 100644
index 0000000000000..5f389d695019c
--- /dev/null
+++ b/Library/Homebrew/test/cask/cli/upgrade_spec.rb
@@ -0,0 +1,211 @@
+require_relative "shared_examples/invalid_option"
+
+describe Hbc::CLI::Upgrade, :cask do
+  it_behaves_like "a command that handles invalid options"
+
+  context "successful upgrade" do
+    let(:installed) {
+      [
+        "outdated/local-caffeine",
+        "outdated/local-transmission",
+        "outdated/auto-updates",
+      ]
+    }
+
+    before(:example) do
+      installed.each { |cask| Hbc::CLI::Install.run(cask) }
+
+      allow_any_instance_of(described_class).to receive(:verbose?).and_return(true)
+    end
+
+    describe 'without --greedy it ignores the Casks with "version latest" or "auto_updates true"' do
+      it "updates all the installed Casks when no token is provided" do
+        local_caffeine = Hbc::CaskLoader.load("local-caffeine")
+        local_caffeine_path = Hbc.appdir.join("Caffeine.app")
+        local_transmission = Hbc::CaskLoader.load("local-transmission")
+        local_transmission_path = Hbc.appdir.join("Transmission.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(local_transmission).to be_installed
+        expect(local_transmission_path).to be_a_directory
+        expect(local_transmission.versions).to include("2.60")
+
+        described_class.run
+
+        expect(local_caffeine).to be_installed
+        expect(local_caffeine_path).to be_a_directory
+        expect(local_caffeine.versions).to include("1.2.3")
+
+        expect(local_transmission).to be_installed
+        expect(local_transmission_path).to be_a_directory
+        expect(local_transmission.versions).to include("2.61")
+      end
+
+      it "updates only the Casks specified in the command line" do
+        local_caffeine = Hbc::CaskLoader.load("local-caffeine")
+        local_caffeine_path = Hbc.appdir.join("Caffeine.app")
+        local_transmission = Hbc::CaskLoader.load("local-transmission")
+        local_transmission_path = Hbc.appdir.join("Transmission.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(local_transmission).to be_installed
+        expect(local_transmission_path).to be_a_directory
+        expect(local_transmission.versions).to include("2.60")
+
+        described_class.run("local-caffeine")
+
+        expect(local_caffeine).to be_installed
+        expect(local_caffeine_path).to be_a_directory
+        expect(local_caffeine.versions).to include("1.2.3")
+
+        expect(local_transmission).to be_installed
+        expect(local_transmission_path).to be_a_directory
+        expect(local_transmission.versions).to include("2.60")
+      end
+
+      it 'updates "auto_updates" and "latest" Casks when their tokens are provided in the command line' do
+        local_caffeine = Hbc::CaskLoader.load("local-caffeine")
+        local_caffeine_path = Hbc.appdir.join("Caffeine.app")
+        auto_updates = Hbc::CaskLoader.load("auto-updates")
+        auto_updates_path = Hbc.appdir.join("MyFancyApp.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")
+
+        described_class.run("local-caffeine", "auto-updates")
+
+        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")
+      end
+    end
+
+    describe "with --greedy it checks additional Casks" do
+      it 'includes the Casks with "auto_updates true" or "version latest"' do
+        local_caffeine = Hbc::CaskLoader.load("local-caffeine")
+        local_caffeine_path = Hbc.appdir.join("Caffeine.app")
+        auto_updates = Hbc::CaskLoader.load("auto-updates")
+        auto_updates_path = Hbc.appdir.join("MyFancyApp.app")
+        local_transmission = Hbc::CaskLoader.load("local-transmission")
+        local_transmission_path = Hbc.appdir.join("Transmission.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")
+
+        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")
+      end
+
+      it 'does not include the Casks with "auto_updates true" when the version did not change' do
+        cask = Hbc::CaskLoader.load("auto-updates")
+        cask_path = Hbc.appdir.join("MyFancyApp.app")
+
+        expect(cask).to be_installed
+        expect(cask_path).to be_a_directory
+        expect(cask.versions).to include("2.57")
+
+        described_class.run("auto-updates", "--greedy")
+
+        expect(cask).to be_installed
+        expect(cask_path).to be_a_directory
+        expect(cask.versions).to include("2.61")
+
+        described_class.run("auto-updates", "--greedy")
+
+        expect(cask).to be_installed
+        expect(cask_path).to be_a_directory
+        expect(cask.versions).to include("2.61")
+      end
+    end
+  end
+
+  context "failed upgrade" do
+    let(:installed) {
+      [
+        "outdated/bad-checksum",
+        "outdated/will-fail-if-upgraded",
+      ]
+    }
+
+    before(:example) do
+      installed.each { |cask| Hbc::CLI::Install.run(cask) }
+
+      allow_any_instance_of(described_class).to receive(:verbose?).and_return(true)
+    end
+
+    output_reverted = Regexp.new <<~EOS
+      Warning: Reverting upgrade for Cask .*
+    EOS
+
+    it "restores the old Cask if the upgrade failed" do
+      will_fail_if_upgraded = Hbc::CaskLoader.load("will-fail-if-upgraded")
+      will_fail_if_upgraded_path = Hbc.appdir.join("container")
+
+      expect(will_fail_if_upgraded).to be_installed
+      expect(will_fail_if_upgraded_path).to be_a_file
+      expect(will_fail_if_upgraded.versions).to include("1.2.2")
+
+      expect {
+        described_class.run("will-fail-if-upgraded")
+      }.to raise_error(Hbc::CaskError).and output(output_reverted).to_stderr
+
+      expect(will_fail_if_upgraded).to be_installed
+      expect(will_fail_if_upgraded_path).to be_a_file
+      expect(will_fail_if_upgraded.versions).to include("1.2.2")
+      expect(will_fail_if_upgraded.staged_path).to_not exist
+    end
+
+    it "does not restore the old Cask if the upgrade failed pre-install" do
+      bad_checksum = Hbc::CaskLoader.load("bad-checksum")
+      bad_checksum_path = Hbc.appdir.join("Caffeine.app")
+
+      expect(bad_checksum).to be_installed
+      expect(bad_checksum_path).to be_a_directory
+      expect(bad_checksum.versions).to include("1.2.2")
+
+      expect {
+        described_class.run("bad-checksum")
+      }.to raise_error(Hbc::CaskSha256MismatchError).and(not_to_output(output_reverted).to_stderr)
+
+      expect(bad_checksum).to be_installed
+      expect(bad_checksum_path).to be_a_directory
+      expect(bad_checksum.versions).to include("1.2.2")
+      expect(bad_checksum.staged_path).to_not exist
+    end
+  end
+end
diff --git a/Library/Homebrew/test/support/fixtures/cask/Casks/auto-updates.rb b/Library/Homebrew/test/support/fixtures/cask/Casks/auto-updates.rb
index 1cada2561cfb5..4f61455bb1bb6 100644
--- a/Library/Homebrew/test/support/fixtures/cask/Casks/auto-updates.rb
+++ b/Library/Homebrew/test/support/fixtures/cask/Casks/auto-updates.rb
@@ -1,11 +1,11 @@
 cask 'auto-updates' do
   version '2.61'
-  sha256 'e44ffa103fbf83f55c8d0b1bea309a43b2880798dae8620b1ee8da5e1095ec68'
+  sha256 '5633c3a0f2e572cbf021507dec78c50998b398c343232bdfc7e26221d0a5db4d'
 
-  url "file://#{TEST_FIXTURE_DIR}/cask/transmission-2.61.dmg"
-  homepage 'http://example.com/auto-updates'
+  url "file://#{TEST_FIXTURE_DIR}/cask/MyFancyApp.zip"
+  homepage 'http://example.com/MyFancyApp'
 
   auto_updates true
 
-  app 'Transmission.app'
+  app 'MyFancyApp/MyFancyApp.app'
 end
diff --git a/Library/Homebrew/test/support/fixtures/cask/Casks/outdated/auto-updates.rb b/Library/Homebrew/test/support/fixtures/cask/Casks/outdated/auto-updates.rb
index e202f5a1632e7..5844a0762cc7f 100644
--- a/Library/Homebrew/test/support/fixtures/cask/Casks/outdated/auto-updates.rb
+++ b/Library/Homebrew/test/support/fixtures/cask/Casks/outdated/auto-updates.rb
@@ -1,11 +1,11 @@
 cask 'auto-updates' do
   version '2.57'
-  sha256 'e44ffa103fbf83f55c8d0b1bea309a43b2880798dae8620b1ee8da5e1095ec68'
+  sha256 '5633c3a0f2e572cbf021507dec78c50998b398c343232bdfc7e26221d0a5db4d'
 
-  url "file://#{TEST_FIXTURE_DIR}/cask/transmission-2.61.dmg"
-  homepage 'http://example.com/auto-updates'
+  url "file://#{TEST_FIXTURE_DIR}/cask/MyFancyApp.zip"
+  homepage 'http://example.com/MyFancyApp'
 
   auto_updates true
 
-  app 'Transmission.app'
+  app 'MyFancyApp/MyFancyApp.app'
 end
diff --git a/Library/Homebrew/test/support/fixtures/cask/Casks/outdated/bad-checksum.rb b/Library/Homebrew/test/support/fixtures/cask/Casks/outdated/bad-checksum.rb
new file mode 100644
index 0000000000000..5e7e744830225
--- /dev/null
+++ b/Library/Homebrew/test/support/fixtures/cask/Casks/outdated/bad-checksum.rb
@@ -0,0 +1,9 @@
+cask 'bad-checksum' do
+  version '1.2.2'
+  sha256 '67cdb8a02803ef37fdbf7e0be205863172e41a561ca446cd84f0d7ab35a99d94'
+
+  url "file://#{TEST_FIXTURE_DIR}/cask/caffeine.zip"
+  homepage 'http://example.com/local-caffeine'
+
+  app 'Caffeine.app'
+end
diff --git a/Library/Homebrew/test/support/fixtures/cask/Casks/outdated/will-fail-if-upgraded.rb b/Library/Homebrew/test/support/fixtures/cask/Casks/outdated/will-fail-if-upgraded.rb
new file mode 100644
index 0000000000000..7735ffa848a8a
--- /dev/null
+++ b/Library/Homebrew/test/support/fixtures/cask/Casks/outdated/will-fail-if-upgraded.rb
@@ -0,0 +1,9 @@
+cask 'will-fail-if-upgraded' do
+  version '1.2.2'
+  sha256 'fab685fabf73d5a9382581ce8698fce9408f5feaa49fa10d9bc6c510493300f5'
+
+  url "file://#{TEST_FIXTURE_DIR}/cask/container.tar.gz"
+  homepage 'https://example.com/container-tar-gz'
+
+  app 'container'
+end
diff --git a/Library/Homebrew/test/support/fixtures/cask/Casks/will-fail-if-upgraded.rb b/Library/Homebrew/test/support/fixtures/cask/Casks/will-fail-if-upgraded.rb
new file mode 100644
index 0000000000000..99ed4b87cfd08
--- /dev/null
+++ b/Library/Homebrew/test/support/fixtures/cask/Casks/will-fail-if-upgraded.rb
@@ -0,0 +1,9 @@
+cask 'will-fail-if-upgraded' do
+  version '1.2.3'
+  sha256 'e44ffa103fbf83f55c8d0b1bea309a43b2880798dae8620b1ee8da5e1095ec68'
+
+  url "file://#{TEST_FIXTURE_DIR}/cask/transmission-2.61.dmg"
+  homepage 'http://example.com/local-transmission'
+
+  app 'container'
+end