diff --git a/Library/Homebrew/cask/artifact/abstract_uninstall.rb b/Library/Homebrew/cask/artifact/abstract_uninstall.rb
index e53bd28912..6c5f45982f 100644
--- a/Library/Homebrew/cask/artifact/abstract_uninstall.rb
+++ b/Library/Homebrew/cask/artifact/abstract_uninstall.rb
@@ -130,7 +130,12 @@ module Cask
           next if running_processes(bundle_id).empty?
 
           unless User.current.gui?
-            ohai "Not logged into a GUI; skipping quitting application ID '#{bundle_id}'."
+            opoo "Not logged into a GUI; skipping quitting application ID '#{bundle_id}'."
+            next
+          end
+
+          unless User.automation_access?
+            opoo "Skipping quitting application ID '#{bundle_id}'. #{User.automation_access_instructions}"
             next
           end
 
@@ -216,6 +221,11 @@ 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!(
             "osascript",
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 c8b2c50c09..f0e7c56fe1 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 +116,27 @@ 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_processes).with(bundle_id).and_return([[0, "", bundle_id]])
+
+      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_processes).with(bundle_id).and_return([[0, "", bundle_id]])
 
       expect {
         subject.public_send(:"#{artifact_dsl_key}_phase", command: fake_system_command)
-      }.to output(/Not logged into a GUI; skipping quitting application ID 'my.fancy.package.app'\./).to_stdout
+      }.to output(/Not logged into a GUI; skipping quitting application ID 'my.fancy.package.app'\./).to_stderr
     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_processes).with(bundle_id).ordered.and_return([[0, "", bundle_id]])
@@ -139,6 +150,7 @@ 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_processes).with(bundle_id).and_return([[0, "", bundle_id]])
@@ -247,6 +259,8 @@ 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!)
         .with(
           "osascript",
diff --git a/Library/Homebrew/utils/user.rb b/Library/Homebrew/utils/user.rb
index cf93d088d8..96f648d8c1 100644
--- a/Library/Homebrew/utils/user.rb
+++ b/Library/Homebrew/utils/user.rb
@@ -6,6 +6,23 @@ 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?