diff --git a/Library/Homebrew/cask/artifact/abstract_uninstall.rb b/Library/Homebrew/cask/artifact/abstract_uninstall.rb
index 2f7f17595f..7fff5cfe31 100644
--- a/Library/Homebrew/cask/artifact/abstract_uninstall.rb
+++ b/Library/Homebrew/cask/artifact/abstract_uninstall.rb
@@ -270,8 +270,8 @@ module Cask
         end
       end
 
-      def uninstall_login_item(*login_items, command: nil, upgrade_or_reinstall: false, **_)
-        return if upgrade_or_reinstall
+      def uninstall_login_item(*login_items, command: nil, successor: nil, **_)
+        return unless successor.nil?
 
         apps = cask.artifacts.select { |a| a.class.dsl_key == :app }
         derived_login_items = apps.map { |a| { path: a.target } }
diff --git a/Library/Homebrew/cask/artifact/moved.rb b/Library/Homebrew/cask/artifact/moved.rb
index f3fa07be6e..e97a65b6f4 100644
--- a/Library/Homebrew/cask/artifact/moved.rb
+++ b/Library/Homebrew/cask/artifact/moved.rb
@@ -35,14 +35,16 @@ module Cask
 
       private
 
-      def move(adopt: false, force: false, verbose: false, upgrade_or_reinstall: false, reinstall: false,
+      def move(adopt: false, force: false, verbose: false, predecessor: nil, reinstall: false,
                command: nil, **options)
         unless source.exist?
           raise CaskError, "It seems the #{self.class.english_name} source '#{source}' is not there."
         end
 
         if Utils.path_occupied?(target)
-          if upgrade_or_reinstall && target.directory? && target.children.empty?
+          if !predecessor.nil? && target.directory? && target.children.empty? && predecessor.artifacts.any? do |a|
+               a.class.dsl_key == self.class.dsl_key && a.target == target
+             end
             # An upgrade removed the directory contents but left the directory itself (see below).
             unless source.directory?
               if target.parent.writable? && !force
@@ -149,13 +151,15 @@ module Cask
         delete(target, force: force, command: command, **options)
       end
 
-      def delete(target, force: false, upgrade_or_reinstall: false, command: nil, **_)
+      def delete(target, force: false, successor: nil, command: nil, **_)
         ohai "Removing #{self.class.english_name} '#{target}'"
         raise CaskError, "Cannot remove undeletable #{self.class.english_name}." if MacOS.undeletable?(target)
 
         return unless Utils.path_occupied?(target)
 
-        if upgrade_or_reinstall && target.directory?
+        if !successor.nil? && target.directory? && successor.artifacts.any? do |a|
+             a.class.dsl_key == self.class.dsl_key && a.target == self.target
+           end
           # If an app folder is deleted, macOS considers the app uninstalled and removes some data.
           # Remove only the contents to handle this case.
           target.children.each do |child|
diff --git a/Library/Homebrew/cask/installer.rb b/Library/Homebrew/cask/installer.rb
index 96ddcce544..d289e30795 100644
--- a/Library/Homebrew/cask/installer.rb
+++ b/Library/Homebrew/cask/installer.rb
@@ -95,6 +95,7 @@ module Cask
 
         raise CaskAlreadyInstalledError, @cask
       end
+      predecessor = (reinstall? && @cask.installed?) ? @cask : nil
 
       check_conflicts
 
@@ -110,7 +111,7 @@ module Cask
 
       @cask.config = @cask.default_config.merge(old_config)
 
-      install_artifacts
+      install_artifacts(predecessor: predecessor)
 
       if (tap = @cask.tap) && tap.should_report_analytics?
         ::Utils::Analytics.report_event(:cask_install, package_name: @cask.token, tap_name: tap.name,
@@ -148,7 +149,7 @@ on_request: true)
 
       # Always force uninstallation, ignore method parameter
       cask_installer = Installer.new(@cask, verbose: verbose?, force: true, upgrade: upgrade?, reinstall: true)
-      zap? ? cask_installer.zap : cask_installer.uninstall
+      zap? ? cask_installer.zap(successor: @cask) : cask_installer.uninstall(successor: @cask)
     end
 
     sig { returns(String) }
@@ -215,7 +216,7 @@ on_request: true)
       Quarantine.propagate(from: primary_container.path, to: to)
     end
 
-    def install_artifacts
+    def install_artifacts(predecessor: nil)
       artifacts = @cask.artifacts
       already_installed_artifacts = []
 
@@ -229,7 +230,7 @@ on_request: true)
         next if artifact.is_a?(Artifact::Binary) && !binaries?
 
         artifact.install_phase(command: @command, verbose: verbose?, adopt: adopt?, force: force?,
-                               upgrade_or_reinstall: upgrade? || reinstall?)
+                               predecessor: predecessor)
         already_installed_artifacts.unshift(artifact)
       end
 
@@ -391,10 +392,10 @@ on_request: true)
       @cask.download_sha_path.atomic_write(@cask.new_download_sha) if @cask.checksumable?
     end
 
-    def uninstall
+    def uninstall(successor: nil)
       load_installed_caskfile!
       oh1 "Uninstalling Cask #{Formatter.identifier(@cask)}"
-      uninstall_artifacts(clear: true)
+      uninstall_artifacts(clear: true, successor: successor)
       if !reinstall? && !upgrade?
         remove_download_sha
         remove_config_file
@@ -412,8 +413,8 @@ on_request: true)
       FileUtils.rm_f @cask.download_sha_path if @cask.download_sha_path.exist?
     end
 
-    def start_upgrade
-      uninstall_artifacts
+    def start_upgrade(successor:)
+      uninstall_artifacts(successor: successor)
       backup
     end
 
@@ -432,10 +433,10 @@ on_request: true)
       backup_metadata_path.rename @cask.metadata_versioned_path
     end
 
-    def revert_upgrade
+    def revert_upgrade(predecessor)
       opoo "Reverting upgrade for Cask #{@cask}"
       restore_backup
-      install_artifacts
+      install_artifacts(predecessor: predecessor)
     end
 
     def finalize_upgrade
@@ -446,7 +447,7 @@ on_request: true)
       puts summary
     end
 
-    def uninstall_artifacts(clear: false)
+    def uninstall_artifacts(clear: false, successor: nil)
       artifacts = @cask.artifacts
 
       odebug "Uninstalling artifacts"
@@ -456,11 +457,11 @@ on_request: true)
         if artifact.respond_to?(:uninstall_phase)
           odebug "Uninstalling artifact of class #{artifact.class}"
           artifact.uninstall_phase(
-            command:              @command,
-            verbose:              verbose?,
-            skip:                 clear,
-            force:                force?,
-            upgrade_or_reinstall: upgrade? || reinstall?,
+            command:   @command,
+            verbose:   verbose?,
+            skip:      clear,
+            force:     force?,
+            successor: successor,
           )
         end
 
@@ -468,16 +469,16 @@ on_request: true)
 
         odebug "Post-uninstalling artifact of class #{artifact.class}"
         artifact.post_uninstall_phase(
-          command:              @command,
-          verbose:              verbose?,
-          skip:                 clear,
-          force:                force?,
-          upgrade_or_reinstall: upgrade? || reinstall?,
+          command:   @command,
+          verbose:   verbose?,
+          skip:      clear,
+          force:     force?,
+          successor: successor,
         )
       end
     end
 
-    def zap
+    def zap(successor: nil)
       load_installed_caskfile!
       ohai "Implied `brew uninstall --cask #{@cask}`"
       uninstall_artifacts
diff --git a/Library/Homebrew/cask/upgrade.rb b/Library/Homebrew/cask/upgrade.rb
index 17c38f43be..eab3a2342f 100644
--- a/Library/Homebrew/cask/upgrade.rb
+++ b/Library/Homebrew/cask/upgrade.rb
@@ -180,22 +180,22 @@ module Cask
         new_cask_installer.fetch
 
         # Move the old cask's artifacts back to staging
-        old_cask_installer.start_upgrade
+        old_cask_installer.start_upgrade(successor: new_cask)
         # 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_cask_installer.install_artifacts(predecessor: old_cask)
         new_artifacts_installed = true
 
         # If successful, wipe the old cask from staging
         old_cask_installer.finalize_upgrade
       rescue => e
-        new_cask_installer.uninstall_artifacts if new_artifacts_installed
+        new_cask_installer.uninstall_artifacts(successor: old_cask) if new_artifacts_installed
         new_cask_installer.purge_versioned_files
-        old_cask_installer.revert_upgrade if started_upgrade
+        old_cask_installer.revert_upgrade(predecessor: new_cask) if started_upgrade
         raise e
       end
 
diff --git a/Library/Homebrew/test/cask/artifact/app_spec.rb b/Library/Homebrew/test/cask/artifact/app_spec.rb
index a172bd7bc6..aa401e345e 100644
--- a/Library/Homebrew/test/cask/artifact/app_spec.rb
+++ b/Library/Homebrew/test/cask/artifact/app_spec.rb
@@ -323,13 +323,13 @@ describe Cask::Artifact::App, :cask do
       inode = target_path.stat.ino
       expect(contents_path).to exist
 
-      app.uninstall_phase(command: command, force: force, upgrade_or_reinstall: true)
+      app.uninstall_phase(command: command, force: force, successor: cask)
 
       expect(target_path).to exist
       expect(target_path.children).to be_empty
       expect(contents_path).not_to exist
 
-      app.install_phase(command: command, adopt: adopt, force: force, upgrade_or_reinstall: true)
+      app.install_phase(command: command, adopt: adopt, force: force, predecessor: cask)
       expect(target_path).to exist
       expect(target_path.stat.ino).to eq(inode)
 
diff --git a/Library/Homebrew/test/cask/upgrade_spec.rb b/Library/Homebrew/test/cask/upgrade_spec.rb
index 5647f3eceb..d10b53be54 100644
--- a/Library/Homebrew/test/cask/upgrade_spec.rb
+++ b/Library/Homebrew/test/cask/upgrade_spec.rb
@@ -13,6 +13,9 @@ describe Cask::Upgrade, :cask do
   let(:local_transmission) { Cask::CaskLoader.load("local-transmission") }
   let(:local_caffeine_path) { local_caffeine.config.appdir.join("Caffeine.app") }
   let(:local_caffeine) { Cask::CaskLoader.load("local-caffeine") }
+  let(:renamed_app) { Cask::CaskLoader.load("renamed-app") }
+  let(:renamed_app_old_path) { renamed_app.config.appdir.join("OldApp.app") }
+  let(:renamed_app_new_path) { renamed_app.config.appdir.join("NewApp.app") }
   let(:args) { Homebrew::CLI::Args.new }
 
   context "when the upgrade is successful" do
@@ -22,6 +25,7 @@ describe Cask::Upgrade, :cask do
         "outdated/local-transmission",
         "outdated/auto-updates",
         "outdated/version-latest",
+        "outdated/renamed-app",
       ]
     end
 
@@ -41,6 +45,11 @@ describe Cask::Upgrade, :cask do
         expect(local_transmission_path).to be_a_directory
         expect(local_transmission.versions).to include("2.60")
 
+        expect(renamed_app).to be_installed
+        expect(renamed_app_old_path).to be_a_directory
+        expect(renamed_app_new_path).not_to be_a_directory
+        expect(renamed_app.versions).to include("1.0.0")
+
         described_class.upgrade_casks(args: args)
 
         expect(local_caffeine).to be_installed
@@ -50,6 +59,11 @@ describe Cask::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(renamed_app).to be_installed
+        expect(renamed_app_old_path).not_to be_a_directory
+        expect(renamed_app_new_path).to be_a_directory
+        expect(renamed_app.versions).to include("2.0.0")
       end
 
       it "updates only the Casks specified in the command line" do
@@ -61,6 +75,11 @@ describe Cask::Upgrade, :cask do
         expect(local_transmission_path).to be_a_directory
         expect(local_transmission.versions).to include("2.60")
 
+        expect(renamed_app).to be_installed
+        expect(renamed_app_old_path).to be_a_directory
+        expect(renamed_app_new_path).not_to be_a_directory
+        expect(renamed_app.versions).to include("1.0.0")
+
         described_class.upgrade_casks(local_caffeine, args: args)
 
         expect(local_caffeine).to be_installed
@@ -70,6 +89,11 @@ describe Cask::Upgrade, :cask do
         expect(local_transmission).to be_installed
         expect(local_transmission_path).to be_a_directory
         expect(local_transmission.versions).to include("2.60")
+
+        expect(renamed_app).to be_installed
+        expect(renamed_app_old_path).to be_a_directory
+        expect(renamed_app_new_path).not_to be_a_directory
+        expect(renamed_app.versions).to include("1.0.0")
       end
 
       it 'updates "auto_updates" and "latest" Casks when their tokens are provided in the command line' do
@@ -107,6 +131,11 @@ describe Cask::Upgrade, :cask do
         expect(local_transmission_path).to be_a_directory
         expect(local_transmission.versions).to include("2.60")
 
+        expect(renamed_app).to be_installed
+        expect(renamed_app_old_path).to be_a_directory
+        expect(renamed_app_new_path).not_to be_a_directory
+        expect(renamed_app.versions).to include("1.0.0")
+
         expect(version_latest).to be_installed
         expect(version_latest_path_1).to be_a_directory
         expect(version_latest.versions).to include("latest")
@@ -128,6 +157,11 @@ describe Cask::Upgrade, :cask do
         expect(local_transmission_path).to be_a_directory
         expect(local_transmission.versions).to include("2.61")
 
+        expect(renamed_app).to be_installed
+        expect(renamed_app_old_path).not_to be_a_directory
+        expect(renamed_app_new_path).to be_a_directory
+        expect(renamed_app.versions).to include("2.0.0")
+
         expect(version_latest).to be_installed
         expect(version_latest_path_2).to be_a_directory
         expect(version_latest.versions).to include("latest")
@@ -187,6 +221,7 @@ describe Cask::Upgrade, :cask do
         "outdated/local-transmission",
         "outdated/auto-updates",
         "outdated/version-latest",
+        "outdated/renamed-app",
       ]
     end
 
@@ -208,6 +243,11 @@ describe Cask::Upgrade, :cask do
         expect(local_transmission_path).to be_a_directory
         expect(local_transmission.versions).to include("2.60")
 
+        expect(renamed_app).to be_installed
+        expect(renamed_app_old_path).to be_a_directory
+        expect(renamed_app_new_path).not_to be_a_directory
+        expect(renamed_app.versions).to include("1.0.0")
+
         described_class.upgrade_casks(dry_run: true, args: args)
 
         expect(local_caffeine).to be_installed
@@ -219,6 +259,12 @@ describe Cask::Upgrade, :cask do
         expect(local_transmission_path).to be_a_directory
         expect(local_transmission.versions).to include("2.60")
         expect(local_transmission.versions).not_to include("2.61")
+
+        expect(renamed_app).to be_installed
+        expect(renamed_app_old_path).to be_a_directory
+        expect(renamed_app_new_path).not_to be_a_directory
+        expect(renamed_app.versions).to include("1.0.0")
+        expect(renamed_app.versions).not_to include("2.0.0")
       end
 
       it "would update only the Casks specified in the command line" do
@@ -256,6 +302,11 @@ describe Cask::Upgrade, :cask do
         expect(auto_updates_path).to be_a_directory
         expect(auto_updates.versions).to include("2.57")
 
+        expect(renamed_app).to be_installed
+        expect(renamed_app_old_path).to be_a_directory
+        expect(renamed_app_new_path).not_to be_a_directory
+        expect(renamed_app.versions).to include("1.0.0")
+
         described_class.upgrade_casks(local_caffeine, auto_updates, dry_run: true, args: args)
 
         expect(local_caffeine).to be_installed
@@ -267,6 +318,12 @@ describe Cask::Upgrade, :cask do
         expect(auto_updates_path).to be_a_directory
         expect(auto_updates.versions).to include("2.57")
         expect(auto_updates.versions).not_to include("2.61")
+
+        expect(renamed_app).to be_installed
+        expect(renamed_app_old_path).to be_a_directory
+        expect(renamed_app_new_path).not_to be_a_directory
+        expect(renamed_app.versions).to include("1.0.0")
+        expect(renamed_app.versions).not_to include("2.0.0")
       end
     end
 
@@ -286,6 +343,11 @@ describe Cask::Upgrade, :cask do
         expect(local_transmission_path).to be_a_directory
         expect(local_transmission.versions).to include("2.60")
 
+        expect(renamed_app).to be_installed
+        expect(renamed_app_old_path).to be_a_directory
+        expect(renamed_app_new_path).not_to be_a_directory
+        expect(renamed_app.versions).to include("1.0.0")
+
         expect(version_latest).to be_installed
         # Change download sha so that :latest cask decides to update itself
         version_latest.download_sha_path.write("fake download sha")
@@ -308,6 +370,12 @@ describe Cask::Upgrade, :cask do
         expect(local_transmission.versions).to include("2.60")
         expect(local_transmission.versions).not_to include("2.61")
 
+        expect(renamed_app).to be_installed
+        expect(renamed_app_old_path).to be_a_directory
+        expect(renamed_app_new_path).not_to be_a_directory
+        expect(renamed_app.versions).to include("1.0.0")
+        expect(renamed_app.versions).not_to include("2.0.0")
+
         expect(version_latest).to be_installed
         expect(version_latest.outdated_download_sha?).to be(true)
       end
diff --git a/Library/Homebrew/test/support/fixtures/cask/Casks/outdated/renamed-app.rb b/Library/Homebrew/test/support/fixtures/cask/Casks/outdated/renamed-app.rb
new file mode 100644
index 0000000000..e93b90cb8e
--- /dev/null
+++ b/Library/Homebrew/test/support/fixtures/cask/Casks/outdated/renamed-app.rb
@@ -0,0 +1,9 @@
+cask "renamed-app" do
+  version "1.0.0"
+  sha256 "cf001ed6c81820e049dc7a353957dab8936b91f1956ee74ff0b3eb59791f1ad9"
+
+  url "file://#{TEST_FIXTURE_DIR}/cask/old-app.tar.gz"
+  homepage "https://brew.sh/"
+
+  app "OldApp.app"
+end
diff --git a/Library/Homebrew/test/support/fixtures/cask/Casks/renamed-app.rb b/Library/Homebrew/test/support/fixtures/cask/Casks/renamed-app.rb
new file mode 100644
index 0000000000..3e1f367fa5
--- /dev/null
+++ b/Library/Homebrew/test/support/fixtures/cask/Casks/renamed-app.rb
@@ -0,0 +1,9 @@
+cask "renamed-app" do
+  version "2.0.0"
+  sha256 "9f88a6f3d8a7977cd3c116c56ee7a20a3c69e838a1d4946f815a926a57883299"
+
+  url "file://#{TEST_FIXTURE_DIR}/cask/new-app.tar.gz"
+  homepage "https://brew.sh/"
+
+  app "NewApp.app"
+end
diff --git a/Library/Homebrew/test/support/fixtures/cask/NewApp.app/Contents/Info.plist b/Library/Homebrew/test/support/fixtures/cask/NewApp.app/Contents/Info.plist
new file mode 100644
index 0000000000..e69de29bb2
diff --git a/Library/Homebrew/test/support/fixtures/cask/NewApp.app/Contents/MacOS/NewApp b/Library/Homebrew/test/support/fixtures/cask/NewApp.app/Contents/MacOS/NewApp
new file mode 100644
index 0000000000..e69de29bb2
diff --git a/Library/Homebrew/test/support/fixtures/cask/NewApp.app/Contents/PkgInfo b/Library/Homebrew/test/support/fixtures/cask/NewApp.app/Contents/PkgInfo
new file mode 100644
index 0000000000..e69de29bb2
diff --git a/Library/Homebrew/test/support/fixtures/cask/NewApp.app/Contents/Resources/Caffeine.icns b/Library/Homebrew/test/support/fixtures/cask/NewApp.app/Contents/Resources/Caffeine.icns
new file mode 100644
index 0000000000..e69de29bb2
diff --git a/Library/Homebrew/test/support/fixtures/cask/new-app.tar.gz b/Library/Homebrew/test/support/fixtures/cask/new-app.tar.gz
new file mode 100644
index 0000000000..a07fc7c8fe
Binary files /dev/null and b/Library/Homebrew/test/support/fixtures/cask/new-app.tar.gz differ
diff --git a/Library/Homebrew/test/support/fixtures/cask/old-app.tar.gz b/Library/Homebrew/test/support/fixtures/cask/old-app.tar.gz
new file mode 100644
index 0000000000..d02fd7e111
Binary files /dev/null and b/Library/Homebrew/test/support/fixtures/cask/old-app.tar.gz differ