diff --git a/lib/commands/install.js b/lib/commands/install.js
index aaec388..4ba182d 100644
--- a/lib/commands/install.js
+++ b/lib/commands/install.js
@@ -5,11 +5,17 @@ const { loadOsModule } = require('../helpers/load-os-module');
 module.exports = /** @type {import('yargs').CommandModule} */ ({
   command: 'install',
   describe: 'Install text to speech extension and other support',
-  async handler() {
+  builder(yargs) {
+    return yargs.option('unattended', {
+      desc: 'Fail if installation requires human intervention',
+      boolean: true,
+    });
+  },
+  async handler({ unattended }) {
     const installDelegate = loadOsModule('install', {
       darwin: () => require('../install/macos'),
       win32: () => require('../install/win32'),
     });
-    await installDelegate.install();
+    await installDelegate.install({ unattended });
   },
 });
diff --git a/lib/install/macos.js b/lib/install/macos.js
index efbff4d..5637f4e 100644
--- a/lib/install/macos.js
+++ b/lib/install/macos.js
@@ -3,6 +3,7 @@
 const { exec: _exec } = require('child_process');
 const { resolve } = require('path');
 const { promisify } = require('util');
+const { 'interaction.pressKeys': pressKeys } = require('../modules/macos/interaction');
 
 const LSREGISTER_EXECUTABLE_PATH =
   '/System/Library/Frameworks/CoreServices.framework/Versions/Current/Frameworks/LaunchServices.framework/Versions/Current/Support/lsregister';
@@ -22,15 +23,60 @@ const SYSTEM_VOICE_IDENTIFIER = 'com.apple.Fred';
 const PLUGIN_TRIPLET_IDENTIFIER = 'ausp atdg BOCU';
 
 const exec = promisify(_exec);
+const enableKeyAutomationPrompt = `This tool can only be installed on systems which allow automated key pressing.
+Please allow the Terminal application to control your computer (the setting is
+controlled in System Settings > Privacy & Security > Accessibility).`;
 
 /** @typedef {import('child_process').ExecOptions} ExecOptions */
 
 /**
+ * Prompt the user to press any key. Resolves when the user presses a key.
+ *
  * @returns {Promise<void>}
  */
-exports.install = async function () {
+const promptForManualKeyPress = async () => {
+  process.stdout.write('Press any key to continue... ');
+  const wasRaw = process.stdin.isRaw;
+  process.stdin.setRawMode(true);
+  process.stdin.resume();
+  const byteArray = await new Promise(resolve => {
+    process.stdin.once('data', data => resolve(Array.from(data)));
+  });
+
+  process.stdin.pause();
+  process.stdin.setRawMode(wasRaw);
+  process.stdout.write('\n');
+
+  // Honor "Control + C" motion by exiting.
+  if (byteArray[0] === 3) {
+    process.exit(1);
+  }
+};
+
+/**
+ * @param {object} options
+ * @param {boolean} options.unattended - Whether installation should fail if
+ *                                       human intervention is required
+ *
+ * @returns {Promise<void>}
+ */
+exports.install = async function ({ unattended }) {
   const options = await getExecOptions();
 
+  if (!(await canPressKeys())) {
+    if (unattended) {
+      throw new Error('The system cannot automate key pressing.');
+    } else {
+      console.error(enableKeyAutomationPrompt);
+
+      await promptForManualKeyPress();
+
+      if (!(await canPressKeys())) {
+        throw new Error('The system cannot automate key pressing.');
+      }
+    }
+  }
+
   if (await isInstalled()) {
     throw new Error('Already installed');
   }
@@ -55,6 +101,21 @@ exports.uninstall = async function () {
   await unregisterExtensions(options);
 };
 
+/**
+ * Experimentally determine whether the current system supports automated key
+ * pressing by attempting to press an arbitrary key.
+ *
+ * @returns {Promise<boolean>}
+ */
+const canPressKeys = async () => {
+  try {
+    await pressKeys(null, { keys: ['shift'] });
+  } catch ({}) {
+    return false;
+  }
+  return true;
+};
+
 const isInstalled = async function () {
   const { stdout } = await exec(`auval -v ${PLUGIN_TRIPLET_IDENTIFIER}`);
   return /ATDriverGenericMacOSExtension/.test(stdout);