diff --git a/Library/Homebrew/cask/artifact/moved.rb b/Library/Homebrew/cask/artifact/moved.rb
index 3b19f5849d..d41e62cec0 100644
--- a/Library/Homebrew/cask/artifact/moved.rb
+++ b/Library/Homebrew/cask/artifact/moved.rb
@@ -84,8 +84,7 @@ module Cask
 
         Utils.gain_permissions_mkpath(target.dirname, command: command) unless target.dirname.exist?
 
-        if target.directory?
-          Quarantine.ensure_app_management_permissions_granted(app: target, command: command)
+        if target.directory? && Quarantine.app_management_permissions_granted?(app: target, command: command)
           if target.writable?
             source.children.each { |child| FileUtils.move(child, target/child.basename) }
           else
@@ -154,10 +153,11 @@ module Cask
 
         return unless Utils.path_occupied?(target)
 
-        if target.directory? && matching_artifact?(successor)
+        if target.directory? && matching_artifact?(successor) && Quarantine.app_management_permissions_granted?(
+          app: target, command: command,
+        )
           # If an app folder is deleted, macOS considers the app uninstalled and removes some data.
           # Remove only the contents to handle this case.
-          Quarantine.ensure_app_management_permissions_granted(app: target, command: command)
           target.children.each do |child|
             if target.writable? && !force
               child.rmtree
diff --git a/Library/Homebrew/cask/quarantine.rb b/Library/Homebrew/cask/quarantine.rb
index cb402e6955..194c794990 100644
--- a/Library/Homebrew/cask/quarantine.rb
+++ b/Library/Homebrew/cask/quarantine.rb
@@ -192,9 +192,9 @@ module Cask
     # Ensures that Homebrew has permission to update apps on macOS Ventura.
     # This may be granted either through the App Management toggle or the Full Disk Access toggle.
     # The system will only show a prompt for App Management, so we ask the user to grant that.
-    sig { params(app: Pathname, command: T.class_of(SystemCommand)).void }
-    def self.ensure_app_management_permissions_granted(app:, command:)
-      return unless app.directory?
+    sig { params(app: Pathname, command: T.class_of(SystemCommand)).returns(T::Boolean) }
+    def self.app_management_permissions_granted?(app:, command:)
+      return true unless app.directory?
 
       # To get macOS to prompt the user for permissions, we need to actually attempt to
       # modify a file in the app.
@@ -215,7 +215,7 @@ module Cask
         begin
           File.write(test_file, "")
           test_file.delete
-          return
+          return true
         rescue Errno::EACCES
           # Using error handler below
         end
@@ -237,17 +237,19 @@ module Cask
             print_stderr: false,
             sudo:         true,
           )
-          return
+          return true
         rescue ErrorDuringExecution => e
           # We only want to handle "touch" errors here; propagate "sudo" errors up
           raise e unless e.stderr.include?("touch: #{test_file}: Operation not permitted")
         end
       end
 
-      odie <<~EOF
-        Your terminal needs permission to update apps.
-        Go to Settings > Security and Privacy > App Management, or look for a notification saying your terminal was prevented from modifying apps.
+      opoo <<~EOF
+        Your terminal does not have App Management permissions, so Homebrew will delete and reinstall the app.
+        This may result in some configurations (like notification settings or location in the Dock/Launchpad) being lost.
+        To fix this, go to Settings > Security and Privacy > App Management and turn on the switch for your terminal.
       EOF
+      false
     end
   end
 end
diff --git a/Library/Homebrew/test/cask/artifact/app_spec.rb b/Library/Homebrew/test/cask/artifact/app_spec.rb
index 3dc19a2cc4..ed94017311 100644
--- a/Library/Homebrew/test/cask/artifact/app_spec.rb
+++ b/Library/Homebrew/test/cask/artifact/app_spec.rb
@@ -329,13 +329,16 @@ describe Cask::Artifact::App, :cask do
     end
 
     describe "when the system blocks modifying apps" do
-      it "does not delete files" do
+      it "uninstalls and reinstalls the app" do
         target_contents_path = target_path.join("Contents")
 
         expect(File).to receive(:write).with(target_path / ".homebrew-write-test",
                                              instance_of(String)).and_raise(Errno::EACCES)
 
-        expect { app.uninstall_phase(command: command, force: force, successor: cask) }.to raise_error(SystemExit)
+        app.uninstall_phase(command: command, force: force, successor: cask)
+        expect(target_path).not_to exist
+
+        app.install_phase(command: command, adopt: adopt, force: force, predecessor: cask)
         expect(target_contents_path).to exist
       end
     end
@@ -368,7 +371,7 @@ describe Cask::Artifact::App, :cask do
       end
 
       describe "when the system blocks modifying apps" do
-        it "does not delete files" do
+        it "uninstalls and reinstalls the app" do
           target_contents_path = target_path.join("Contents")
 
           allow(command).to receive(:run!).with(any_args).and_call_original
@@ -380,7 +383,10 @@ describe Cask::Artifact::App, :cask do
             .and_raise(ErrorDuringExecution.new([], status: 1,
 output: [[:stderr, "touch: #{target_path}/.homebrew-write-test: Operation not permitted\n"]], secrets: []))
 
-          expect { app.uninstall_phase(command: command, force: force, successor: cask) }.to raise_error(SystemExit)
+          app.uninstall_phase(command: command, force: force, successor: cask)
+          expect(target_path).not_to exist
+
+          app.install_phase(command: command, adopt: adopt, force: force, predecessor: cask)
           expect(target_contents_path).to exist
         end
       end