Add cask upgrade quit opt-out

- Support `--no-quit` for users who need cask apps left open.
- Add `HOMEBREW_NO_UPGRADE_QUIT_CASKS` for persistent opt-out.
- Cover command, upgrade and uninstall-stanza paths with regressions.

Author: MikeMcQuaid

Library/Homebrew/cask/artifact/uninstall.rb

@@ -13,10 +13,11 @@ class Uninstall < AbstractUninstall
         params(
           upgrade:   T::Boolean,
           reinstall: T::Boolean,
+          quit:      T::Boolean,
           options:   T.anything,
         ).void
       }
-      def uninstall_phase(upgrade: false, reinstall: false, **options)
+      def uninstall_phase(upgrade: false, reinstall: false, quit: true, **options)
         raw_on_upgrade = directives[:on_upgrade]
         on_upgrade_syms =
           case raw_on_upgrade
@@ -31,6 +32,7 @@ def uninstall_phase(upgrade: false, reinstall: false, **options)
 
         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) &&

Library/Homebrew/cask/installer.rb

@@ -587,9 +587,9 @@ def remove_download_sha
       @cask.download_sha_path.parent.rmdir_if_possible
     end
 
-    sig { params(successor: T.nilable(Cask)).void }
-    def start_upgrade(successor:)
-      uninstall_artifacts(successor:)
+    sig { params(successor: T.nilable(Cask), quit: T::Boolean).void }
+    def start_upgrade(successor:, quit: true)
+      uninstall_artifacts(successor:, quit:)
       backup
     end
 
@@ -638,8 +638,8 @@ def finalize_upgrade
       puts summary
     end
 
-    sig { params(clear: T::Boolean, successor: T.nilable(Cask)).void }
-    def uninstall_artifacts(clear: false, successor: nil)
+    sig { params(clear: T::Boolean, successor: T.nilable(Cask), quit: T::Boolean).void }
+    def uninstall_artifacts(clear: false, successor: nil, quit: true)
       odebug "Uninstalling artifacts"
       odebug "#{::Utils.pluralize("artifact", artifacts.length, include_count: true)} defined", artifacts
 
@@ -659,15 +659,17 @@ def uninstall_artifacts(clear: false, successor: nil)
           )
 
           odebug "Uninstalling artifact of class #{artifact.class}"
-          artifact.uninstall_phase(
+          uninstall_options = {
             command:   @command,
             verbose:   verbose?,
             skip:      clear,
             force:     force?,
             successor:,
             upgrade:   upgrade?,
             reinstall: reinstall?,
-          )
+          }
+          uninstall_options[:quit] = quit if artifact.is_a?(Artifact::Uninstall)
+          artifact.uninstall_phase(**uninstall_options)
         end
 
         next unless artifact.respond_to?(:post_uninstall_phase)

Library/Homebrew/cask/upgrade.rb

@@ -112,6 +112,7 @@ def self.show_upgrade_summary(cask_upgrades, dry_run: false)
         binaries:             T.nilable(T::Boolean),
         quarantine:           T.nilable(T::Boolean),
         require_sha:          T.nilable(T::Boolean),
+        quit:                 T::Boolean,
         skip_prefetch:        T::Boolean,
         show_upgrade_summary: T::Boolean,
         download_queue:       T.nilable(Homebrew::DownloadQueue),
@@ -135,6 +136,7 @@ def self.upgrade_casks!(
       binaries: nil,
       quarantine: nil,
       require_sha: nil,
+      quit: true,
       skip_prefetch: false,
       show_upgrade_summary: true,
       download_queue: nil,
@@ -261,7 +263,7 @@ def self.upgrade_casks!(
         upgrade_cask(
           old_cask, new_cask,
           binaries:, force:, skip_cask_deps:, verbose:,
-          quarantine:, require_sha:, download_queue:
+          quarantine:, require_sha:, quit:, download_queue:
         )
       rescue => e
         new_exception = e.exception("#{new_cask.full_name}: #{e}")
@@ -331,14 +333,15 @@ def self.reopen_apps_after_upgrade(old_cask)
         force:          T.nilable(T::Boolean),
         quarantine:     T.nilable(T::Boolean),
         require_sha:    T.nilable(T::Boolean),
+        quit:           T::Boolean,
         skip_cask_deps: T.nilable(T::Boolean),
         verbose:        T.nilable(T::Boolean),
         download_queue: Homebrew::DownloadQueue,
       ).void
     }
     def self.upgrade_cask(
       old_cask, new_cask,
-      binaries:, force:, quarantine:, require_sha:, skip_cask_deps:, verbose:, download_queue:
+      binaries:, force:, quarantine:, require_sha:, quit:, skip_cask_deps:, verbose:, download_queue:
     )
       require "cask/installer"
 
@@ -402,7 +405,7 @@ def self.upgrade_cask(
         end
 
         # Move the old cask's artifacts back to staging
-        old_cask_installer.start_upgrade(successor: new_cask)
+        old_cask_installer.start_upgrade(successor: new_cask, quit:)
         # And flag it so in case of error
         started_upgrade = true
 
@@ -423,9 +426,9 @@ def self.upgrade_cask(
         # If successful, wipe the old cask from staging.
         old_cask_installer.finalize_upgrade
 
-        reopen_apps_after_upgrade(old_cask)
+        reopen_apps_after_upgrade(old_cask) if quit
       rescue => e
-        new_cask_installer.uninstall_artifacts(successor: old_cask) if new_artifacts_installed
+        new_cask_installer.uninstall_artifacts(successor: old_cask, quit:) if new_artifacts_installed
         new_cask_installer.purge_versioned_files
         old_cask_installer.revert_upgrade(predecessor: new_cask) if started_upgrade
         raise e

Library/Homebrew/cmd/upgrade.rb

@@ -109,6 +109,10 @@ class FinalUpgradeSummary < T::Struct
           [:switch, "--skip-cask-deps", {
             description: "Skip installing cask dependencies.",
           }],
+          [:switch, "--no-quit", {
+            description: "Prevent running cask applications from being quit during upgrade.",
+            env:         :no_upgrade_quit_casks,
+          }],
           [:switch, "-g", "--greedy", {
             description: "Also include casks with `version :latest` and `auto_updates true` casks " \
                          "that would otherwise be skipped.",
@@ -778,6 +782,7 @@ def upgrade_outdated_casks!(casks, skip_prefetch: false, show_upgrade_summary: t
           quarantine:           args.quarantine?,
           require_sha:          args.require_sha?,
           skip_cask_deps:       args.skip_cask_deps?,
+          quit:                 !args.no_quit?,
           verbose:              args.verbose?,
           quiet:                args.quiet?,
           skip_prefetch:,

Library/Homebrew/env_config.rb

@@ -483,6 +483,10 @@ module EnvConfig
         boolean:     true,
         hidden:      true, # odeprecated: remove in 5.2.0
       },
+      HOMEBREW_NO_UPGRADE_QUIT_CASKS:            {
+        description: "If set, `brew upgrade` will not quit running applications for casks during upgrades.",
+        boolean:     true,
+      },
       HOMEBREW_NO_VERIFY_ATTESTATIONS:           {
         description: "If set, Homebrew will not verify cryptographic attestations of build provenance for bottles " \
                      "from homebrew-core.",

Library/Homebrew/sorbet/rbi/dsl/homebrew/cmd/upgrade_cmd.rbi

@@ -25,6 +25,17 @@
           expect(quit_called).to be true
         end
 
+        it "skips :quit during upgrade when quit is false" do
+          quit_called = false
+          allow(artifact).to receive(:dispatch_uninstall_directive) do |directive, **options|
+            quit_called ||= directive == :quit && options[:command] == fake_system_command
+          end
+
+          artifact.uninstall_phase(upgrade: true, quit: false, command: fake_system_command)
+
+          expect(quit_called).to be false
+        end
+
         it "invokes :quit during reinstall" do
           quit_called = false
           allow(artifact).to receive(:dispatch_uninstall_directive) do |directive, **options|

Library/Homebrew/sorbet/rbi/dsl/homebrew/env_config.rbi

@@ -172,6 +172,20 @@ def write_info_plist(path, short_version:, bundle_version:)
         expect(summary_deprecated).to include("local-caffeine")
       end
 
+      it "passes the quit option to cask upgrades" do
+        expect(described_class).to receive(:upgrade_cask) do |_, _, **options|
+          expect(options[:quit]).to be(false)
+        end
+
+        described_class.upgrade_casks!(
+          local_caffeine,
+          quit:                 false,
+          skip_prefetch:        true,
+          show_upgrade_summary: false,
+          args:,
+        )
+      end
+
       it "excludes pinned Casks" do
         local_caffeine.pin
         summary_pinned = []

Library/Homebrew/test/cask/artifact/uninstall_spec.rb

@@ -160,6 +160,28 @@ def install_formula_version(name, version, optlinked: false)
     cmd.send(:upgrade_outdated_casks!, [])
   end
 
+  it "passes --no-quit to cask upgrades" do
+    cmd = described_class.new(["--cask", "--no-quit"])
+
+    expect(Cask::Upgrade).to receive(:upgrade_casks!) do |*_, **kwargs|
+      expect(kwargs[:quit]).to be(false)
+    end
+
+    cmd.send(:upgrade_outdated_casks!, [])
+  end
+
+  it "passes HOMEBREW_NO_UPGRADE_QUIT_CASKS to cask upgrades" do
+    with_env("HOMEBREW_NO_UPGRADE_QUIT_CASKS" => "1") do
+      cmd = described_class.new(["--cask"])
+
+      expect(Cask::Upgrade).to receive(:upgrade_casks!) do |*_, **kwargs|
+        expect(kwargs[:quit]).to be(false)
+      end
+
+      cmd.send(:upgrade_outdated_casks!, [])
+    end
+  end
+
   it "prints formula and cask ask plans before upgrading" do
     cmd = described_class.new(["--ask"])