diff --git a/Library/Homebrew/cask/artifact/abstract_uninstall.rb b/Library/Homebrew/cask/artifact/abstract_uninstall.rb
index 71ce23677c..9278bff97d 100644
--- a/Library/Homebrew/cask/artifact/abstract_uninstall.rb
+++ b/Library/Homebrew/cask/artifact/abstract_uninstall.rb
@@ -124,6 +124,11 @@ module Cask
           end
       end
 
+      def automation_access_instructions
+        "Enable Automation Access for “Terminal > System Events” in " \
+        "“System Preferences > Security > Privacy > Automation” if you haven't already."
+      end
+
       # :quit/:signal must come before :kext so the kext will not be in use by a running process
       def uninstall_quit(*bundle_ids, command: nil, **_)
         bundle_ids.each do |bundle_id|
@@ -134,11 +139,6 @@ module Cask
             next
           end
 
-          unless User.automation_access?
-            opoo "Skipping quitting application ID '#{bundle_id}'. #{User.automation_access_instructions}"
-            next
-          end
-
           ohai "Quitting application '#{bundle_id}'..."
 
           begin
@@ -153,8 +153,7 @@ module Cask
               end
             end
           rescue Timeout::Error
-            opoo "Application '#{bundle_id}' did not quit."
-            next
+            opoo "Application '#{bundle_id}' did not quit. #{automation_access_instructions}"
           end
         end
       end
@@ -242,19 +241,18 @@ module Cask
             ["name", item]
           end
 
-          unless User.automation_access?
-            opoo "Skipping removal of login item #{id}. #{User.automation_access_instructions}"
-            next
-          end
-
           ohai "Removing login item #{id}"
-          system_command!(
+
+          result = system_command(
             "osascript",
             args: [
               "-e",
               %Q(tell application "System Events" to delete every login item whose #{type} is #{id.to_s.inspect}),
             ],
           )
+
+          opoo "Removal of login item #{id} failed. #{automation_access_instructions}" unless result.success?
+
           sleep 1
         end
       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 91eff61b6f..209be079fa 100644
--- a/Library/Homebrew/test/cask/artifact/shared_examples/uninstall_zap.rb
+++ b/Library/Homebrew/test/cask/artifact/shared_examples/uninstall_zap.rb
@@ -116,16 +116,6 @@ shared_examples "#uninstall_phase or #zap_phase" do
     let(:cask) { Cask::CaskLoader.load(cask_path("with-#{artifact_dsl_key}-quit")) }
     let(:bundle_id) { "my.fancy.package.app" }
 
-    it "is skipped when the user does not have automation access" do
-      allow(User).to receive(:automation_access?).and_return false
-      allow(User.current).to receive(:gui?).and_return true
-      allow(subject).to receive(:running?).with(bundle_id).and_return(true)
-
-      expect {
-        subject.public_send(:"#{artifact_dsl_key}_phase", command: fake_system_command)
-      }.to output(/Skipping quitting application ID 'my.fancy.package.app'\./).to_stderr
-    end
-
     it "is skipped when the user is not a GUI user" do
       allow(User.current).to receive(:gui?).and_return false
       allow(subject).to receive(:running?).with(bundle_id).and_return(true)
@@ -136,7 +126,6 @@ shared_examples "#uninstall_phase or #zap_phase" do
     end
 
     it "quits a running application" do
-      allow(User).to receive(:automation_access?).and_return true
       allow(User.current).to receive(:gui?).and_return true
 
       expect(subject).to receive(:running?).with(bundle_id).ordered.and_return(true)
@@ -150,7 +139,6 @@ shared_examples "#uninstall_phase or #zap_phase" do
     end
 
     it "tries to quit the application for 10 seconds" do
-      allow(User).to receive(:automation_access?).and_return true
       allow(User.current).to receive(:gui?).and_return true
 
       allow(subject).to receive(:running?).with(bundle_id).and_return(true)
@@ -257,14 +245,12 @@ shared_examples "#uninstall_phase or #zap_phase" do
     let(:cask) { Cask::CaskLoader.load(cask_path("with-#{artifact_dsl_key}-login-item")) }
 
     it "is supported" do
-      allow(User).to receive(:automation_access?).and_return true
-
-      expect(subject).to receive(:system_command!)
+      expect(subject).to receive(:system_command)
         .with(
           "osascript",
           args: ["-e", 'tell application "System Events" to delete every login item whose name is "Fancy"'],
         )
-        .and_return(instance_double("SystemCommand::Result"))
+        .and_return(instance_double("SystemCommand::Result", success?: true))
 
       subject.public_send(:"#{artifact_dsl_key}_phase", command: fake_system_command)
     end
diff --git a/Library/Homebrew/utils/user.rb b/Library/Homebrew/utils/user.rb
index 96f648d8c1..cf93d088d8 100644
--- a/Library/Homebrew/utils/user.rb
+++ b/Library/Homebrew/utils/user.rb
@@ -6,23 +6,6 @@ require "etc"
 require "system_command"
 
 class User < DelegateClass(String)
-  def self.automation_access?
-    return @automation_access if defined?(@automation_access)
-
-    *_, status = system_command "osascript", args: [
-      "-e", "with timeout of 0.5 seconds",
-      "-e", 'tell application "System Events" to get volume settings',
-      "-e", "end timeout"
-    ], print_stderr: false
-
-    @automation_access = status.success?
-  end
-
-  def self.automation_access_instructions
-    "Enable Automation Access for “Terminal > System Events” in " \
-    "“System Preferences > Security > Privacy > Automation”."
-  end
-
   def gui?
     out, _, status = system_command "who"
     return false unless status.success?