diff --git a/ui/desktop/tests/end2end/targets.spec.js b/ui/desktop/tests/end2end/targets.spec.js
new file mode 100644
index 000000000..4e05aeed2
--- /dev/null
+++ b/ui/desktop/tests/end2end/targets.spec.js
@@ -0,0 +1,128 @@
+/* eslint-disable no-undef */
+const { test, expect } = require('@playwright/test');
+const { _electron: electron } = require('playwright');
+const path = require('path');
+
+let electronApp = null;
+const returnScreenshotPath = (fileName) => {
+  const screenshotPath = 'tests/end2end/screenshots/targets/';
+  const screenshotFormat = '.png';
+  return path.join(screenshotPath, fileName).concat(screenshotFormat);
+};
+
+test.beforeEach(async () => {
+  electronApp = await electron.launch({
+    executablePath:
+      'electron-app/out/Boundary-darwin-arm64/Boundary.app/Contents/MacOS/Boundary',
+    env: {
+      NODE_ENV: 'test',
+      BYPASS_APP_UPDATER: true,
+    },
+  });
+});
+
+test.afterEach(async () => {
+  electronApp.close();
+  electronApp = null; // Not sure we should do this.
+});
+
+test.describe('Targets end to end test suite', async () => {
+  test('Connects to a target', async () => {
+    const boundaryWindow = await electronApp.firstWindow(); // The window that contains the app.
+    // Override local storage origin
+    await boundaryWindow.evaluate(() =>
+      window.localStorage.setItem('desktop:origin', null)
+    );
+
+    const originValue = 'http://localhost:9200';
+    const authLoginNameValue = 'admin';
+    const authLoginPasswordValue = 'password';
+
+    // Fill the origin input
+    await boundaryWindow.waitForSelector('.ember-text-field');
+    await boundaryWindow.fill('.ember-text-field', originValue);
+
+    // Click the submit button
+    // Due to an error with await boundaryWindow.click('button[type="submit"]'); we are using a workaround.
+    // More info about it here: https://github.com/microsoft/playwright/issues/1808
+    await boundaryWindow.waitForSelector('button[type="submit"]');
+    await boundaryWindow.$eval('button[type="submit"]', (element) =>
+      element.click()
+    );
+    // Fill user & password
+    await boundaryWindow.fill('[name="identification"]', authLoginNameValue);
+    await boundaryWindow.fill('[name="password"]', authLoginPasswordValue);
+
+    // Click submit
+    await boundaryWindow.waitForSelector('button[type="submit"]');
+    await boundaryWindow.$eval('button[type="submit"]', (element) =>
+      element.click()
+    );
+    // Check we are in Targets
+    await boundaryWindow.waitForSelector('h2 >> text=Targets');
+    expect(await boundaryWindow.innerText('h2 >> text=Targets')).toEqual(
+      'Targets '
+    );
+
+    // Click connect to a target
+    await boundaryWindow.waitForSelector('table.rose-table');
+    await boundaryWindow.$eval(
+      'table.rose-table >> tbody >> tr >> nth=0 >> button >> text=Connect',
+      (element) => element.click()
+    );
+
+    // The target popup opens
+    await boundaryWindow.waitForSelector('section.dialog-detail');
+    // Take screenshot
+    await boundaryWindow.screenshot({
+      path: returnScreenshotPath('targetConnectionDetails'),
+      fullPage: true,
+    });
+    // Click copyable in popup
+    // TODO: read clipboard value. Running into issues reading clipboard, so will take a shortcut for now
+    await boundaryWindow.$eval(
+      'section.dialog-detail >> div.rose-dialog-body >> button',
+      (element) => element.click()
+    );
+    // Temporary: persist proxy from target
+    const persistedProxy = await boundaryWindow.innerText(
+      'section.dialog-detail >> div.rose-dialog-body >> span.copyable-content'
+    );
+
+    // Click close popup
+    await boundaryWindow.$eval(
+      'section.dialog-detail >> footer >> button',
+      (element) => element.click()
+    );
+
+    // On left nav menu, click Sessions
+    await boundaryWindow.waitForSelector('section.rose-layout-global >> aside');
+    await boundaryWindow.$eval(
+      'section.rose-layout-global >> aside >> nav >> a >> text=Sessions',
+      (element) => element.click()
+    );
+
+    // Take screenshot
+    await boundaryWindow.screenshot({
+      path: returnScreenshotPath('sessions'),
+      fullPage: true,
+    });
+
+    // Check the right session has status pending.
+    await boundaryWindow.waitForSelector(
+      'main >> div.rose-layout-page-body >> table.rose-table'
+    );
+    // Select Proxy
+    const currentProxy = await boundaryWindow.innerText(
+      'div.rose-layout-page-body >> table >> tbody >> tr >> nth=0 >> td >> nth=1 >> .copyable-content'
+    );
+    const currentStatus = await boundaryWindow.innerText(
+      'div.rose-layout-page-body >> table >> tbody >> tr >> nth=0 >> td >> nth=3 >> .rose-badge-body'
+    );
+
+    expect(await persistedProxy).toEqual(await currentProxy);
+    expect(await currentStatus).toEqual('pending');
+    // TODO: before closing the app we should terminate sessions.
+    // TODO: add test to check if sessions are not terminated we promp the confirmation dialog
+  });
+});