From 463e9241934c3bf24b07457568e859cd672510d3 Mon Sep 17 00:00:00 2001
From: Bevan Kay <email@bevankay.me>
Date: Thu, 10 Sep 2026 10:58:27 +1000
Subject: [PATCH] cask: run zap and uninstall directives together

- `brew uninstall --zap` ran the whole `zap` stanza only after every
  artifact had been removed, so a `zap` `script:` inside the app could
  never run: `mullvad-vpn` and `private-internet-access` both raise.
- Run `zap` directives up to `script:` in the `uninstall` stanza's
  pass, before the artifacts are removed, `uninstall` arguments first.
- Keep `zap` `pkgutil:`, `delete:` and `trash:` after the artifacts and
  `uninstall_postflight` steps, as before: `betwixt`'s postflight reads
  a certificate that its `zap` stanza trashes.
- Run `rmdir:` for both stanzas after the artifacts are removed, so a
  directory that held only those artifacts is seen as empty.
- Pass `clear: true` when zapping, as `brew uninstall` already does, so
  an artifact target removed by `uninstall` `delete:` is skipped rather
  than raising for casks such as `cloudnet`, `mqttfx` and `pokerstars`.
- `zap` `signal:` now follows the same upgrade and reinstall rules as
  `uninstall` `signal:`.
- Head the output with `Zapping Cask`, like `Uninstalling Cask`, as
  `Dispatching zap stanza` no longer marks a separate pass.
---
 .../cask/artifact/abstract_uninstall.rb       | 62 +++++++++---
 Library/Homebrew/cask/artifact/uninstall.rb   | 33 +------
 Library/Homebrew/cask/artifact/zap.rb         | 14 +--
 Library/Homebrew/cask/installer.rb            | 99 +++++++++----------
 .../artifact/shared_examples/uninstall_zap.rb | 41 ++++----
 .../test/cask/artifact/uninstall_spec.rb      |  2 +-
 .../Homebrew/test/cask/artifact/zap_spec.rb   | 10 +-
 Library/Homebrew/test/cask/installer_spec.rb  | 54 ++++++++++
 Library/Homebrew/test/cask/reinstall_spec.rb  |  2 +-
 .../cask/Casks/with-uninstall-and-zap.rb      | 27 +++++
 .../cask/Casks/with-uninstall-delete-app.rb   | 15 +++
 .../cask/Casks/with-uninstall-rmdir-app.rb    | 15 +++
 12 files changed, 241 insertions(+), 133 deletions(-)
 create mode 100644 Library/Homebrew/test/support/fixtures/cask/Casks/with-uninstall-and-zap.rb
 create mode 100644 Library/Homebrew/test/support/fixtures/cask/Casks/with-uninstall-delete-app.rb
 create mode 100644 Library/Homebrew/test/support/fixtures/cask/Casks/with-uninstall-rmdir-app.rb

diff --git a/Library/Homebrew/cask/artifact/abstract_uninstall.rb b/Library/Homebrew/cask/artifact/abstract_uninstall.rb
index 6bab703063..ec5c843420 100644
--- a/Library/Homebrew/cask/artifact/abstract_uninstall.rb
+++ b/Library/Homebrew/cask/artifact/abstract_uninstall.rb
@@ -38,11 +38,54 @@ module Cask
         :on_upgrade,
       ].freeze
 
+      UPGRADE_REINSTALL_SKIP_DIRECTIVES = [:signal].freeze
+
       sig { params(cask: Cask, directives: DirectivesType).returns(AbstractUninstall) }
       def self.from_args(cask, **directives)
         new(cask, **directives)
       end
 
+      # Dispatches the directives of one or more `uninstall`/`zap` stanzas in a single
+      # `ORDERED_DIRECTIVES` pass, the earlier stanza's first at each step, so that
+      # zapping runs `zap` directives alongside the `uninstall` stanza's. Each stanza's
+      # `deferred_directives` are skipped, and are the only ones run when `deferred:`.
+      sig {
+        params(
+          artifacts: T::Array[AbstractUninstall],
+          command:   T.class_of(SystemCommand),
+          deferred:  T::Boolean,
+          force:     T::Boolean,
+          successor: T.nilable(Cask),
+          upgrade:   T::Boolean,
+          reinstall: T::Boolean,
+          quit:      T::Boolean,
+        ).void
+      }
+      def self.dispatch_directives(artifacts, command:, deferred: false, force: false, successor: nil,
+                                   upgrade: false, reinstall: false, quit: true)
+        ORDERED_DIRECTIVES.each do |directive_sym|
+          next if directive_sym == :quit && !quit
+
+          artifacts.each do |artifact|
+            next if artifact.deferred_directives.include?(directive_sym) != deferred
+
+            if (upgrade || reinstall) &&
+               UPGRADE_REINSTALL_SKIP_DIRECTIVES.include?(directive_sym) &&
+               Array(artifact.directives[:on_upgrade]).map { |name| name.to_s.to_sym }.exclude?(directive_sym)
+              next
+            end
+
+            artifact.dispatch_uninstall_directive(directive_sym, command:, force:, successor:, upgrade:)
+          end
+        end
+      end
+
+      # Directives that wait until the cask's artifacts have been removed and its
+      # `uninstall_postflight` steps have run, so that directories which held only
+      # those artifacts are seen as empty.
+      sig { overridable.returns(T::Array[Symbol]) }
+      def deferred_directives = [:rmdir]
+
       sig { returns(T::Hash[Symbol, DirectivesType]) }
       attr_reader :directives
 
@@ -180,22 +223,7 @@ module Cask
           end
       end
 
-      private
-
-      sig {
-        params(
-          command:   T.class_of(SystemCommand),
-          force:     T::Boolean,
-          successor: T.nilable(Cask),
-          upgrade:   T::Boolean,
-        ).void
-      }
-      def dispatch_uninstall_directives(command:, force: false, successor: nil, upgrade: false)
-        ORDERED_DIRECTIVES.each do |directive_sym|
-          dispatch_uninstall_directive(directive_sym, command:, force:, successor:, upgrade:)
-        end
-      end
-
+      # Runs this stanza's `directive_sym` directive, if it has one.
       # The `uninstall_*` methods are dispatched dynamically, so they take these
       # options uniformly and ignore the ones they do not need.
       sig {
@@ -216,6 +244,8 @@ module Cask
              command:, force:, successor:, upgrade:)
       end
 
+      private
+
       sig { returns(Symbol) }
       def stanza
         self.class.dsl_key
diff --git a/Library/Homebrew/cask/artifact/uninstall.rb b/Library/Homebrew/cask/artifact/uninstall.rb
index 4636b07cbb..d882e07643 100644
--- a/Library/Homebrew/cask/artifact/uninstall.rb
+++ b/Library/Homebrew/cask/artifact/uninstall.rb
@@ -7,8 +7,6 @@ module Cask
   module Artifact
     # Artifact corresponding to the `uninstall` stanza.
     class Uninstall < AbstractUninstall
-      UPGRADE_REINSTALL_SKIP_DIRECTIVES = [:signal].freeze
-
       sig {
         params(
           command:   T.class_of(SystemCommand),
@@ -23,34 +21,7 @@ module Cask
       }
       def uninstall_phase(command:, skip: false, force: false, verbose: false, successor: nil, upgrade: false,
                           reinstall: false, quit: true)
-        raw_on_upgrade = directives[:on_upgrade]
-        on_upgrade_syms =
-          case raw_on_upgrade
-          when Symbol
-            [raw_on_upgrade]
-          when Array
-            raw_on_upgrade.map(&:to_sym)
-          else
-            []
-          end
-        on_upgrade_set = on_upgrade_syms.to_set
-
-        filtered_directives = ORDERED_DIRECTIVES.filter do |directive_sym|
-          next false if directive_sym == :rmdir
-          next false if directive_sym == :quit && !quit
-
-          if (upgrade || reinstall) &&
-             UPGRADE_REINSTALL_SKIP_DIRECTIVES.include?(directive_sym) &&
-             on_upgrade_set.exclude?(directive_sym)
-            next false
-          end
-
-          true
-        end
-
-        filtered_directives.each do |directive_sym|
-          dispatch_uninstall_directive(directive_sym, command:, force:, successor:, upgrade:)
-        end
+        AbstractUninstall.dispatch_directives([self], command:, force:, successor:, upgrade:, reinstall:, quit:)
       end
 
       sig {
@@ -63,7 +34,7 @@ module Cask
         ).void
       }
       def post_uninstall_phase(command:, skip: false, force: false, verbose: false, successor: nil)
-        dispatch_uninstall_directive(:rmdir, command:, force:, successor:)
+        AbstractUninstall.dispatch_directives([self], command:, deferred: true, force:, successor:)
       end
     end
   end
diff --git a/Library/Homebrew/cask/artifact/zap.rb b/Library/Homebrew/cask/artifact/zap.rb
index 336312b1bb..8b0545b79f 100644
--- a/Library/Homebrew/cask/artifact/zap.rb
+++ b/Library/Homebrew/cask/artifact/zap.rb
@@ -7,16 +7,10 @@ module Cask
   module Artifact
     # Artifact corresponding to the `zap` stanza.
     class Zap < AbstractUninstall
-      sig {
-        params(
-          command: T.class_of(SystemCommand),
-          force:   T::Boolean,
-          verbose: T::Boolean,
-        ).void
-      }
-      def zap_phase(command:, force: false, verbose: false)
-        dispatch_uninstall_directives(command:, force:)
-      end
+      # Removing files also waits, as `uninstall` steps may still need them, e.g. to
+      # identify a keychain certificate to delete.
+      sig { override.returns(T::Array[Symbol]) }
+      def deferred_directives = [:pkgutil, :delete, :trash, :rmdir]
     end
   end
 end
diff --git a/Library/Homebrew/cask/installer.rb b/Library/Homebrew/cask/installer.rb
index fb3ea53311..708242188f 100644
--- a/Library/Homebrew/cask/installer.rb
+++ b/Library/Homebrew/cask/installer.rb
@@ -715,67 +715,64 @@ on_request: true)
       puts summary
     end
 
-    sig { params(clear: T::Boolean, successor: T.nilable(Cask), quit: T::Boolean).void }
-    def uninstall_artifacts(clear: false, successor: nil, quit: true)
+    sig {
+      params(clear: T::Boolean, successor: T.nilable(Cask), quit: T::Boolean, zap_stanzas: T::Array[Artifact::Zap])
+        .void
+    }
+    def uninstall_artifacts(clear: false, successor: nil, quit: true, zap_stanzas: [])
       odebug "Uninstalling artifacts"
       odebug "#{::Utils.pluralize("artifact", artifacts.length, include_count: true)} defined", artifacts
 
-      artifacts.each do |artifact|
-        if artifact.respond_to?(:uninstall_phase)
-          artifact = T.cast(
-            artifact,
-            T.any(
-              Artifact::AbstractFlightBlock,
-              Artifact::GeneratedCompletion,
-              Artifact::KeyboardLayout,
-              Artifact::Moved,
-              Artifact::PostflightSteps,
-              Artifact::PreflightSteps,
-              Artifact::Qlplugin,
-              Artifact::Symlinked,
-              Artifact::Uninstall,
-              Artifact::UninstallPostflightSteps,
-              Artifact::UninstallPreflightSteps,
-            ),
-          )
+      directive_artifacts = [*artifacts.grep(Artifact::Uninstall), *zap_stanzas]
 
-          odebug "Uninstalling artifact of class #{artifact.class}"
-          if artifact.is_a?(Artifact::Uninstall)
-            artifact.uninstall_phase(command: @command, verbose: verbose?, skip: clear, force: force?, successor:,
-                                     upgrade: upgrade?, reinstall: reinstall?, quit:)
-          else
-            artifact.uninstall_phase(command: @command, verbose: verbose?, skip: clear, force: force?, successor:,
-                                     upgrade: upgrade?, reinstall: reinstall?)
-          end
-        end
-
-        next unless artifact.respond_to?(:post_uninstall_phase)
-
-        artifact = T.cast(artifact, Artifact::Uninstall)
-
-        odebug "Post-uninstalling artifact of class #{artifact.class}"
-        artifact.post_uninstall_phase(
-          command:   @command,
-          verbose:   verbose?,
-          skip:      clear,
-          force:     force?,
-          successor:,
-        )
+      preflight, removable = T.cast(
+        artifacts.grep_v(Artifact::AbstractUninstall).select { |artifact| artifact.respond_to?(:uninstall_phase) },
+        T::Array[
+          T.any(
+            Artifact::AbstractFlightBlock,
+            Artifact::GeneratedCompletion,
+            Artifact::KeyboardLayout,
+            Artifact::Moved,
+            Artifact::PostflightSteps,
+            Artifact::PreflightSteps,
+            Artifact::Qlplugin,
+            Artifact::Symlinked,
+            Artifact::UninstallPostflightSteps,
+            Artifact::UninstallPreflightSteps,
+          ),
+        ],
+      ).partition do |artifact|
+        order = artifact.sort_order
+        uninstall_order = order.fetch(Artifact::Uninstall)
+        order.fetch(artifact.class, uninstall_order) < uninstall_order
       end
+
+      preflight.each do |artifact|
+        odebug "Uninstalling artifact of class #{artifact.class}"
+        artifact.uninstall_phase(command: @command, verbose: verbose?, skip: clear, force: force?, successor:,
+                                 upgrade: upgrade?, reinstall: reinstall?)
+      end
+
+      Artifact::AbstractUninstall.dispatch_directives(directive_artifacts, command: @command, force: force?,
+                                                      successor:, upgrade: upgrade?, reinstall: reinstall?, quit:)
+
+      removable.each do |artifact|
+        odebug "Uninstalling artifact of class #{artifact.class}"
+        artifact.uninstall_phase(command: @command, verbose: verbose?, skip: clear, force: force?, successor:,
+                                 upgrade: upgrade?, reinstall: reinstall?)
+      end
+
+      Artifact::AbstractUninstall.dispatch_directives(directive_artifacts, command: @command, deferred: true,
+                                                                           force: force?, successor:)
     end
 
     sig { void }
     def zap
       load_installed_caskfile!
-      uninstall_artifacts
-      if (zap_stanzas = @cask.artifacts.grep(Artifact::Zap)).empty?
-        opoo "No zap stanza present for Cask '#{@cask}'"
-      else
-        ohai "Dispatching zap stanza"
-        zap_stanzas.each do |stanza|
-          stanza.zap_phase(command: @command, verbose: verbose?, force: force?)
-        end
-      end
+      oh1 "Zapping Cask #{Formatter.identifier(@cask)}"
+      zap_stanzas = @cask.artifacts.grep(Artifact::Zap)
+      opoo "No zap stanza present for Cask '#{@cask}'" if zap_stanzas.empty?
+      uninstall_artifacts(clear: true, zap_stanzas:)
       ohai "Removing all staged versions of Cask '#{@cask}'"
       purge_caskroom_path
     end
diff --git a/Library/Homebrew/test/cask/artifact/shared_examples/uninstall_zap.rb b/Library/Homebrew/test/cask/artifact/shared_examples/uninstall_zap.rb
index 61801225f7..32959970c1 100644
--- a/Library/Homebrew/test/cask/artifact/shared_examples/uninstall_zap.rb
+++ b/Library/Homebrew/test/cask/artifact/shared_examples/uninstall_zap.rb
@@ -4,7 +4,7 @@
 require "benchmark"
 require "services/system"
 
-RSpec.shared_examples "#uninstall_phase or #zap_phase" do
+RSpec.shared_examples "uninstall/zap directive dispatch" do
   extend Test::Helper::TestEach
 
   subject { artifact }
@@ -18,6 +18,11 @@ RSpec.shared_examples "#uninstall_phase or #zap_phase" do
     allow(Cask::Artifact::AbstractUninstall).to receive(:ancestor_bundle_ids).and_return([])
   end
 
+  def dispatch_stanza(**options)
+    described_class.dispatch_directives([subject], **options)
+    described_class.dispatch_directives([subject], deferred: true, **options)
+  end
+
   context "when using :launchctl" do
     let(:cask) { Cask::CaskLoader.load(cask_path("with-#{artifact_dsl_key}-launchctl")) }
     let(:launchctl_list_cmd) { %w[/bin/launchctl list my.fancy.package.service] }
@@ -50,7 +55,7 @@ RSpec.shared_examples "#uninstall_phase or #zap_phase" do
         must_succeed: false, sudo: false, sudo_as_root: false)
         .and_return(instance_double(SystemCommand::Result, success?: true))
 
-      subject.public_send(:"#{artifact_dsl_key}_phase", command: fake_system_command)
+      dispatch_stanza(command: fake_system_command)
     end
 
     it "works when job is owned by system" do
@@ -66,7 +71,7 @@ RSpec.shared_examples "#uninstall_phase or #zap_phase" do
         must_succeed: false, sudo: true, sudo_as_root: true)
         .and_return(instance_double(SystemCommand::Result, success?: true))
 
-      subject.public_send(:"#{artifact_dsl_key}_phase", command: fake_system_command)
+      dispatch_stanza(command: fake_system_command)
     end
 
     it "does not fail when sudo removal fails" do
@@ -83,7 +88,7 @@ RSpec.shared_examples "#uninstall_phase or #zap_phase" do
         .and_return(instance_double(SystemCommand::Result, success?: false))
 
       expect do
-        subject.public_send(:"#{artifact_dsl_key}_phase", command: fake_system_command)
+        dispatch_stanza(command: fake_system_command)
       end.not_to raise_error
     end
   end
@@ -135,7 +140,7 @@ RSpec.shared_examples "#uninstall_phase or #zap_phase" do
         must_succeed: false, sudo: true, sudo_as_root: true)
         .and_return(instance_double(SystemCommand::Result, success?: true))
 
-      subject.public_send(:"#{artifact_dsl_key}_phase", command: fake_system_command)
+      dispatch_stanza(command: fake_system_command)
     end
 
     it "returns the matching launchctl services" do
@@ -168,7 +173,7 @@ RSpec.shared_examples "#uninstall_phase or #zap_phase" do
       expect(main_pkg).to receive(:uninstall)
       expect(agent_pkg).to receive(:uninstall)
 
-      subject.public_send(:"#{artifact_dsl_key}_phase", command: fake_system_command)
+      dispatch_stanza(command: fake_system_command)
     end
   end
 
@@ -192,7 +197,7 @@ RSpec.shared_examples "#uninstall_phase or #zap_phase" do
       expect(subject).to receive(:system_command!)
         .with("/bin/rm", args: ["-rf", "/Library/Extensions/FancyPackage.kext"], sudo: true, sudo_as_root: true)
 
-      subject.public_send(:"#{artifact_dsl_key}_phase", command: fake_system_command)
+      dispatch_stanza(command: fake_system_command)
     end
   end
 
@@ -205,7 +210,7 @@ RSpec.shared_examples "#uninstall_phase or #zap_phase" do
       allow(subject).to receive(:running?).with(bundle_id).and_return(true)
 
       expect do
-        subject.public_send(:"#{artifact_dsl_key}_phase", command: fake_system_command)
+        dispatch_stanza(command: fake_system_command)
       end.to output(/Not logged into a GUI; skipping quitting application ID 'my.fancy.package.app'\./).to_stderr
     end
 
@@ -216,7 +221,7 @@ RSpec.shared_examples "#uninstall_phase or #zap_phase" do
 
       expect(subject).not_to receive(:quit)
       expect do
-        subject.public_send(:"#{artifact_dsl_key}_phase", command: fake_system_command)
+        dispatch_stanza(command: fake_system_command)
       end.to output(/Skipping quitting application 'my.fancy.package.app' as `brew` is running inside it\./)
         .to_stderr
     end
@@ -230,7 +235,7 @@ RSpec.shared_examples "#uninstall_phase or #zap_phase" do
       expect(subject).to receive(:running?).with(bundle_id).ordered.and_return(false)
 
       expect do
-        subject.public_send(:"#{artifact_dsl_key}_phase", command: fake_system_command)
+        dispatch_stanza(command: fake_system_command)
       end.to output(/Application 'my.fancy.package.app' quit successfully\./).to_stdout
     end
 
@@ -244,7 +249,7 @@ RSpec.shared_examples "#uninstall_phase or #zap_phase" do
       allow(Timeout).to receive(:timeout).and_raise(Timeout::Error)
 
       expect do
-        subject.public_send(:"#{artifact_dsl_key}_phase", command: fake_system_command)
+        dispatch_stanza(command: fake_system_command)
       end.to output(/Application 'my.fancy.package.app' did not quit\./).to_stderr
     end
   end
@@ -267,12 +272,10 @@ RSpec.shared_examples "#uninstall_phase or #zap_phase" do
         expect(Process).to receive(:kill).with(signal, *unix_pids).and_return(1)
       end
 
-      subject.public_send(:"#{artifact_dsl_key}_phase", command: fake_system_command)
+      dispatch_stanza(command: fake_system_command)
     end
 
     it "does not send signal when upgrading or reinstalling" do
-      skip "only uninstall has upgrade and reinstall phases" if artifact_dsl_key == :zap
-
       allow(subject).to receive(:running_processes).with(bundle_id)
                                                    .and_return(unix_pids.map { |pid| [pid, 0, bundle_id] })
 
@@ -280,8 +283,8 @@ RSpec.shared_examples "#uninstall_phase or #zap_phase" do
         expect(Process).not_to receive(:kill)
       end
 
-      subject.public_send(:"#{artifact_dsl_key}_phase", upgrade: true, command: fake_system_command)
-      subject.public_send(:"#{artifact_dsl_key}_phase", reinstall: true, command: fake_system_command)
+      dispatch_stanza(upgrade: true, command: fake_system_command)
+      dispatch_stanza(reinstall: true, command: fake_system_command)
     end
   end
 
@@ -315,7 +318,7 @@ RSpec.shared_examples "#uninstall_phase or #zap_phase" do
       it "is supported" do
         expect(paths).to all(exist)
 
-        subject.public_send(:"#{artifact_dsl_key}_phase", command: fake_system_command)
+        dispatch_stanza(command: fake_system_command)
 
         paths.each do |path|
           expect(path).not_to exist
@@ -344,7 +347,7 @@ RSpec.shared_examples "#uninstall_phase or #zap_phase" do
           )
 
         InstallHelper.install_without_artifacts(cask)
-        subject.public_send(:"#{artifact_dsl_key}_phase", command: fake_system_command)
+        dispatch_stanza(command: fake_system_command)
       end
     end
   end
@@ -360,7 +363,7 @@ RSpec.shared_examples "#uninstall_phase or #zap_phase" do
         )
         .and_return(instance_double(SystemCommand::Result, success?: true))
 
-      subject.public_send(:"#{artifact_dsl_key}_phase", command: fake_system_command)
+      dispatch_stanza(command: fake_system_command)
     end
   end
 end
diff --git a/Library/Homebrew/test/cask/artifact/uninstall_spec.rb b/Library/Homebrew/test/cask/artifact/uninstall_spec.rb
index 9f838a7832..ae697bb049 100644
--- a/Library/Homebrew/test/cask/artifact/uninstall_spec.rb
+++ b/Library/Homebrew/test/cask/artifact/uninstall_spec.rb
@@ -9,7 +9,7 @@ RSpec.describe Cask::Artifact::Uninstall, :cask do
   describe "#uninstall_phase" do
     let(:fake_system_command) { NeverSudoSystemCommand }
 
-    include_examples "#uninstall_phase or #zap_phase"
+    include_examples "uninstall/zap directive dispatch"
 
     context "when sudo is disabled" do
       let(:cask) { Cask::CaskLoader.load(cask_path("with-uninstall-launchctl")) }
diff --git a/Library/Homebrew/test/cask/artifact/zap_spec.rb b/Library/Homebrew/test/cask/artifact/zap_spec.rb
index 7f04af3bde..fc48dcde3b 100644
--- a/Library/Homebrew/test/cask/artifact/zap_spec.rb
+++ b/Library/Homebrew/test/cask/artifact/zap_spec.rb
@@ -4,8 +4,8 @@
 require_relative "shared_examples/uninstall_zap"
 
 RSpec.describe Cask::Artifact::Zap, :cask do
-  describe "#zap_phase" do
-    include_examples "#uninstall_phase or #zap_phase"
+  describe "directive dispatch" do
+    include_examples "uninstall/zap directive dispatch"
 
     context "when using :rmdir" do
       subject(:artifact) { cask.artifacts.find { |a| a.is_a?(described_class) } }
@@ -29,7 +29,7 @@ RSpec.describe Cask::Artifact::Zap, :cask do
         expect(empty_directory_tree).to exist
         expect(ds_store).to exist
 
-        artifact.zap_phase(command: fake_system_command)
+        described_class.dispatch_directives([artifact], command: fake_system_command, deferred: true)
 
         expect(ds_store).not_to exist
         expect(empty_directory).not_to exist
@@ -47,7 +47,9 @@ RSpec.describe Cask::Artifact::Zap, :cask do
         after { FileUtils.rm_rf target }
 
         it "leaves the link and its target alone" do
-          expect { artifact.zap_phase(command: fake_system_command) }.not_to raise_error
+          expect do
+            described_class.dispatch_directives([artifact], command: fake_system_command, deferred: true)
+          end.not_to raise_error
 
           expect(empty_directory).to be_a_symlink
           expect(target.join("nested")).to be_a_directory
diff --git a/Library/Homebrew/test/cask/installer_spec.rb b/Library/Homebrew/test/cask/installer_spec.rb
index e673c8177d..1252897e82 100644
--- a/Library/Homebrew/test/cask/installer_spec.rb
+++ b/Library/Homebrew/test/cask/installer_spec.rb
@@ -5,6 +5,8 @@ require "cask/installer"
 require "install"
 
 RSpec.describe Cask::Installer, :cask do
+  let(:rmdir_directory) { Pathname("#{TEST_TMPDIR}/rmdir_app_directory") }
+
   def stub_dmg_extraction
     allow(UnpackStrategy::Dmg).to receive(:can_extract?).and_return(true)
     allow_any_instance_of(UnpackStrategy::Dmg).to receive(:extract_nestedly) do |_strategy, to:, **|
@@ -512,6 +514,44 @@ RSpec.describe Cask::Installer, :cask do
       expect(caffeine).not_to be_installed
       expect(Pathname(caffeine.config.appdir).join("Caffeine.app")).not_to be_a_symlink
     end
+
+    it "zap method runs zap directives alongside uninstall ones, removing files last" do
+      cask = Cask::CaskLoader.load(cask_path("with-uninstall-and-zap"))
+      dispatched = []
+      allow_any_instance_of(Cask::Artifact::AbstractUninstall)
+        .to receive(:dispatch_uninstall_directive) do |artifact, directive, **|
+          dispatched << [artifact.class.dsl_key, directive] if artifact.directives[directive].present?
+        end
+      allow_any_instance_of(Cask::Artifact::UninstallPostflightSteps)
+        .to receive(:uninstall_phase) { dispatched << [:uninstall_postflight] }
+
+      described_class.new(cask, command: NeverSudoSystemCommand).zap
+
+      expect(dispatched).to eq [
+        [:uninstall, :quit], [:zap, :quit], [:zap, :script], [:uninstall, :delete],
+        [:uninstall_postflight], [:zap, :pkgutil], [:zap, :delete], [:zap, :trash]
+      ]
+    end
+
+    it "zap method tolerates an artifact target removed by an uninstall directive" do
+      cask = Cask::CaskLoader.load(cask_path("with-uninstall-delete-app"))
+      described_class.new(cask, command: NeverSudoSystemCommand).install
+
+      expect { described_class.new(cask, command: NeverSudoSystemCommand).zap }.not_to raise_error
+    end
+
+    context "when an `rmdir:` directory holds an artifact" do
+      after { FileUtils.rm_rf rmdir_directory }
+
+      it "zap method removes directories emptied by removing artifacts" do
+        cask = Cask::CaskLoader.load(cask_path("with-uninstall-rmdir-app"))
+        described_class.new(cask).install
+
+        described_class.new(cask).zap
+
+        expect(rmdir_directory).not_to exist
+      end
+    end
   end
 
   describe "#backup" do
@@ -530,6 +570,20 @@ RSpec.describe Cask::Installer, :cask do
   end
 
   describe "uninstall" do
+    context "with an `uninstall rmdir:` directory holding an artifact" do
+      after { FileUtils.rm_rf rmdir_directory }
+
+      it "removes the directory once the artifact is removed" do
+        cask = Cask::CaskLoader.load(cask_path("with-uninstall-rmdir-app"))
+        described_class.new(cask).install
+
+        described_class.new(cask).uninstall
+
+        expect(rmdir_directory/"nested").not_to exist
+        expect(rmdir_directory).to exist
+      end
+    end
+
     it "fully uninstalls a Cask" do
       caffeine = Cask::CaskLoader.load(cask_path("local-caffeine"))
       installer = described_class.new(caffeine)
diff --git a/Library/Homebrew/test/cask/reinstall_spec.rb b/Library/Homebrew/test/cask/reinstall_spec.rb
index 040004ffce..e821042546 100644
--- a/Library/Homebrew/test/cask/reinstall_spec.rb
+++ b/Library/Homebrew/test/cask/reinstall_spec.rb
@@ -31,9 +31,9 @@ RSpec.describe Cask::Reinstall, :cask do
     Cask::Installer.new(caffeine).install
 
     output = Regexp.new <<~EOS
+      ==> Zapping Cask local-caffeine
       ==> Backing up App 'Caffeine.app' to '.*Caffeine.app'
       ==> Removing App '.*Caffeine.app'
-      ==> Dispatching zap stanza
       ==> Trashing files:
       .*org.example.caffeine.plist
       ==> Removing all staged versions of Cask 'local-caffeine'
diff --git a/Library/Homebrew/test/support/fixtures/cask/Casks/with-uninstall-and-zap.rb b/Library/Homebrew/test/support/fixtures/cask/Casks/with-uninstall-and-zap.rb
new file mode 100644
index 0000000000..7df871b770
--- /dev/null
+++ b/Library/Homebrew/test/support/fixtures/cask/Casks/with-uninstall-and-zap.rb
@@ -0,0 +1,27 @@
+# typed: false
+
+cask "with-uninstall-and-zap" do
+  version "1.2.3"
+  sha256 "8c62a2b791cf5f0da6066a0a4b6e85f62949cd60975da062df44adf887f4370b"
+
+  url "file://#{TEST_FIXTURE_DIR}/cask/MyFancyPkg.zip"
+  homepage "https://brew.sh/fancy-pkg"
+
+  pkg "MyFancyPkg/Fancy.pkg"
+
+  uninstall_postflight_steps do
+    remove "uninstall-postflight-marker"
+  end
+
+  uninstall quit:   "my.fancy.package.app",
+            delete: "#{TEST_TMPDIR}/absolute_path"
+
+  zap quit:    "my.fancy.package.app",
+      script:  {
+        executable: "MyFancyPkg/FancyUninstaller.tool",
+        args:       ["--please"],
+      },
+      pkgutil: "my.fancy.package.*",
+      delete:  "#{TEST_TMPDIR}/zap_delete_path",
+      trash:   "#{TEST_TMPDIR}/zap_path"
+end
diff --git a/Library/Homebrew/test/support/fixtures/cask/Casks/with-uninstall-delete-app.rb b/Library/Homebrew/test/support/fixtures/cask/Casks/with-uninstall-delete-app.rb
new file mode 100644
index 0000000000..8a0cbd3bb8
--- /dev/null
+++ b/Library/Homebrew/test/support/fixtures/cask/Casks/with-uninstall-delete-app.rb
@@ -0,0 +1,15 @@
+# typed: false
+
+cask "with-uninstall-delete-app" do
+  version "1.2.3"
+  sha256 "67cdb8a02803ef37fdbf7e0be205863172e41a561ca446cd84f0d7ab35a99d94"
+
+  url "file://#{TEST_FIXTURE_DIR}/cask/caffeine.zip"
+  homepage "https://brew.sh/"
+
+  app "Caffeine.app"
+
+  uninstall delete: "#{appdir}/Caffeine.app"
+
+  zap trash: "#{TEST_TMPDIR}/with_uninstall_delete_app_zap"
+end
diff --git a/Library/Homebrew/test/support/fixtures/cask/Casks/with-uninstall-rmdir-app.rb b/Library/Homebrew/test/support/fixtures/cask/Casks/with-uninstall-rmdir-app.rb
new file mode 100644
index 0000000000..158ee6d9b9
--- /dev/null
+++ b/Library/Homebrew/test/support/fixtures/cask/Casks/with-uninstall-rmdir-app.rb
@@ -0,0 +1,15 @@
+# typed: false
+
+cask "with-uninstall-rmdir-app" do
+  version "1.2.3"
+  sha256 "67cdb8a02803ef37fdbf7e0be205863172e41a561ca446cd84f0d7ab35a99d94"
+
+  url "file://#{TEST_FIXTURE_DIR}/cask/caffeine.zip"
+  homepage "https://brew.sh/"
+
+  app "Caffeine.app", target: "#{TEST_TMPDIR}/rmdir_app_directory/nested/Caffeine.app"
+
+  uninstall rmdir: "#{TEST_TMPDIR}/rmdir_app_directory/nested"
+
+  zap rmdir: "#{TEST_TMPDIR}/rmdir_app_directory"
+end