diff --git a/packages/client-app/internal_packages/sync-health-checker/lib/main.es6 b/packages/client-app/internal_packages/sync-health-checker/lib/main.es6
new file mode 100644
index 000000000..e7ca045d1
--- /dev/null
+++ b/packages/client-app/internal_packages/sync-health-checker/lib/main.es6
@@ -0,0 +1,9 @@
+import SyncHealthChecker from './sync-health-checker'
+
+export function activate() {
+  SyncHealthChecker.start()
+}
+
+export function deactivate() {
+  SyncHealthChecker.stop()
+}
diff --git a/packages/client-app/internal_packages/sync-health-checker/lib/sync-health-checker.es6 b/packages/client-app/internal_packages/sync-health-checker/lib/sync-health-checker.es6
new file mode 100644
index 000000000..70ba7dbe9
--- /dev/null
+++ b/packages/client-app/internal_packages/sync-health-checker/lib/sync-health-checker.es6
@@ -0,0 +1,111 @@
+import {ipcRenderer} from 'electron'
+import {AccountStore, Actions, NylasAPI, NylasAPIRequest} from 'nylas-exports'
+
+const CHECK_HEALTH_INTERVAL = 5 * 60 * 1000;
+
+class SyncHealthChecker {
+  constructor() {
+    this._lastSyncActivity = null
+    this._interval = null
+  }
+
+  start() {
+    if (this._interval) {
+      console.warn('SyncHealthChecker has already been started')
+    } else {
+      this._interval = setInterval(this._checkSyncHealth, CHECK_HEALTH_INTERVAL)
+    }
+  }
+
+  stop() {
+    clearInterval(this._interval)
+    this._interval = null
+  }
+
+  // This is a separate function so the request can be manipulated in the specs
+  _buildRequest = () => {
+    return new NylasAPIRequest({
+      api: NylasAPI,
+      options: {
+        accountId: AccountStore.accounts()[0].id,
+        path: `/health`,
+      },
+    });
+  }
+
+  _checkSyncHealth = async () => {
+    try {
+      const request = this._buildRequest()
+      const response = await request.run()
+      this._lastSyncActivity = response
+    } catch (err) {
+      if (/ECONNREFUSED/i.test(err.toString())) {
+        this._onWorkerWindowUnavailable()
+      } else {
+        err.message = `Error checking sync health: ${err.message}`
+        NylasEnv.reportError(err)
+      }
+    }
+  }
+
+  _onWorkerWindowUnavailable() {
+    let extraData = {};
+
+    // Extract data that we want to report. We'll report the entire
+    // _lastSyncActivity object, but it'll probably be useful if we can segment
+    // by the data in the oldest or newest entry, so we report those as
+    // individual values too.
+    const lastActivityEntries = Object.entries(this._lastSyncActivity || {})
+    if (lastActivityEntries.length > 0) {
+      const times = lastActivityEntries.map((entry) => entry[1].time)
+      const now = Date.now()
+
+      const maxTime = Math.max(...times)
+      const mostRecentEntry = lastActivityEntries.find((entry) => entry[1].time === maxTime)
+      const [mostRecentActivityAccountId, {
+        activity: mostRecentActivity,
+        time: mostRecentActivityTime,
+      }] = mostRecentEntry;
+      const mostRecentDuration = now - mostRecentActivityTime
+
+      const minTime = Math.min(...times)
+      const leastRecentEntry = lastActivityEntries.find((entry) => entry[1].time === minTime)
+      const [leastRecentActivityAccountId, {
+        activity: leastRecentActivity,
+        time: leastRecentActivityTime,
+      }] = leastRecentEntry;
+      const leastRecentDuration = now - leastRecentActivityTime
+
+      extraData = {
+        mostRecentActivity,
+        mostRecentActivityTime,
+        mostRecentActivityAccountId,
+        mostRecentDuration,
+        leastRecentActivity,
+        leastRecentActivityTime,
+        leastRecentActivityAccountId,
+        leastRecentDuration,
+      }
+    }
+
+    NylasEnv.reportError(new Error('Worker window was unavailable'), {
+      // This information isn't as useful in Sentry, but include it here until
+      // the data is actually sent to Mixpanel. (See the TODO below)
+      lastActivityPerAccount: this._lastSyncActivity,
+      ...extraData,
+    })
+
+    // TODO: This doesn't make it to Mixpanel because our analytics process
+    // lives in the worker window. We should move analytics to the main process.
+    // https://phab.nylas.com/T8029
+    Actions.recordUserEvent('Worker Window Unavailable', {
+      lastActivityPerAccount: this._lastSyncActivity,
+      ...extraData,
+    })
+
+    console.log(`Detected worker window was unavailable. Restarting it.`, this._lastSyncActivity)
+    ipcRenderer.send('ensure-worker-window')
+  }
+}
+
+export default new SyncHealthChecker()
diff --git a/packages/client-app/internal_packages/sync-health-checker/package.json b/packages/client-app/internal_packages/sync-health-checker/package.json
new file mode 100644
index 000000000..f4682568b
--- /dev/null
+++ b/packages/client-app/internal_packages/sync-health-checker/package.json
@@ -0,0 +1,11 @@
+{
+  "name": "sync-health-checker",
+  "version": "0.1.0",
+  "main": "./lib/main",
+  "description": "Periodically ping the sync process to ensure it's running",
+  "license": "GPL-3.0",
+  "private": true,
+  "engines": {
+    "nylas": "*"
+  }
+}
diff --git a/packages/client-app/src/browser/application.es6 b/packages/client-app/src/browser/application.es6
index 3768dceb4..fd36e19b9 100644
--- a/packages/client-app/src/browser/application.es6
+++ b/packages/client-app/src/browser/application.es6
@@ -465,6 +465,10 @@ export default class Application extends EventEmitter {
       }
     });
 
+    ipcMain.on('ensure-worker-window', () => {
+      this.windowManager.ensureWindow(WindowManager.WORK_WINDOW)
+    })
+
     ipcMain.on('inline-style-parse', (event, {html, key}) => {
       const juice = require('juice');
       let out = null;