diff --git a/.azure-pipelines.yml b/.azure-pipelines.yml
index 3348f07..ac65b2f 100644
--- a/.azure-pipelines.yml
+++ b/.azure-pipelines.yml
@@ -11,14 +11,6 @@ parameters:
 - name: testJobs
   type: object
   default:
-  - iosVersion: 12
-    xcodeVersion: 10
-    iosDeviceName: iPhone 6
-    vmImage: macOS-10.14
-  - iosVersion: 12.4
-    xcodeVersion: 10.3
-    iosDeviceName: iPhone X
-    vmImage: macOS-10.14
   - iosVersion: 13.2
     xcodeVersion: 11.2
     iosDeviceName: iPhone 11
@@ -31,7 +23,10 @@ parameters:
     xcodeVersion: 12
     iosDeviceName: iPhone 11
     vmImage: macOS-10.15
-
+  - iosVersion: 14.4
+    xcodeVersion: 12.4
+    iosDeviceName: iPhone 12
+    vmImage: macOS-10.15
 
 stages:
 - stage: Unit_Test
diff --git a/lib/simulator-xcode-9.js b/lib/simulator-xcode-9.js
index b748882..b20688d 100644
--- a/lib/simulator-xcode-9.js
+++ b/lib/simulator-xcode-9.js
@@ -4,10 +4,11 @@ import path from 'path';
 import { fs, timing } from 'appium-support';
 import AsyncLock from 'async-lock';
 import log from './logger';
-import { waitForCondition, retryInterval } from 'asyncbox';
+import { waitForCondition } from 'asyncbox';
 import { toBiometricDomainComponent, getDeveloperRoot } from './utils.js';
 import { NSUserDefaults, generateDefaultsCommandArgs } from './defaults-utils';
 import B from 'bluebird';
+import { EventEmitter } from 'events';
 
 const SIMULATOR_SHUTDOWN_TIMEOUT = 15 * 1000;
 const startupLock = new AsyncLock();
@@ -177,30 +178,38 @@ class SimulatorXcode9 extends SimulatorXcode8 {
   }
 
   /**
-   * Boots simulator if not already booted.
+   * Boots Simulator if not already booted.
    * Does nothing if it is already running.
+   * This API does NOT wait until Simulator is fully booted.
    *
-   * @throws {Error} If Simulator is still not running after being booted
+   * @throws {Error} If there was a failure while booting the Simulator.
    */
   async boot () {
-    if (await this.isRunning()) {
-      log.info(`Simulator '${this.udid}' is already running`);
-      return;
-    }
-
-    log.info(`Booting Simulator '${this.udid}'`);
+    const bootEventsEmitter = new EventEmitter();
+    await this.simctl.startBootMonitor({
+      onError: (err) => bootEventsEmitter.emit('failure', err),
+      onFinished: () => bootEventsEmitter.emit('finish'),
+      shouldPreboot: true,
+    });
     try {
-      await this.simctl.bootDevice();
-    } catch (e) {
-      log.warn(e.stderr || e.message);
+      await new B((resolve, reject) => {
+        // Historically this call was always asynchronous,
+        // e.g. it was not waiting until Simulator is fully booted.
+        // So we preserve that behavior, and if no errors are received for a while
+        // then we assume the Simulator booting is still in progress.
+        setTimeout(resolve, 3000);
+        bootEventsEmitter.once('failure', (err) => {
+          if (_.includes(err?.message, 'state: Booted')) {
+            resolve();
+          } else {
+            reject(err);
+          }
+        });
+        bootEventsEmitter.once('finish', resolve);
+      });
+    } finally {
+      bootEventsEmitter.removeAllListeners();
     }
-
-    await retryInterval(5, 1000, async () => {
-      if (!await this.isRunning()) {
-        throw new Error(`Simulator '${this.udid}' is not running after being booted. ` +
-          `Check the Appium log for more details.`);
-      }
-    });
   }
 
   /**
diff --git a/package.json b/package.json
index 484f806..7255f35 100644
--- a/package.json
+++ b/package.json
@@ -36,7 +36,7 @@
     "asyncbox": "^2.3.1",
     "bluebird": "^3.5.1",
     "lodash": "^4.2.1",
-    "node-simctl": "^6.4.0",
+    "node-simctl": "^6.6.0",
     "semver": "^7.0.0",
     "source-map-support": "^0.5.3",
     "teen_process": "^1.3.0",