diff --git a/ui/admin/tests/e2e/helpers/boundary-cli.js b/ui/admin/tests/e2e/helpers/boundary-cli.js
index 26d36c6a2..8d7005d8d 100644
--- a/ui/admin/tests/e2e/helpers/boundary-cli.js
+++ b/ui/admin/tests/e2e/helpers/boundary-cli.js
@@ -4,7 +4,7 @@
  */
 
 /* eslint-disable no-undef */
-const { execSync } = require('child_process');
+const { execSync, exec } = require('child_process');
 
 /**
  * Checks that the boundary cli is available
@@ -36,3 +36,44 @@ exports.authenticateBoundaryCli = async () => {
     console.log(`${e.stderr}`);
   }
 };
+
+/**
+ * Uses the boundary CLI to connect to the specified target
+ * @param {string} targetId ID of the target to be connected to
+ * @returns ChildProcess representing the result of the command execution
+ */
+exports.connectToTarget = async (targetId) => {
+  let connect;
+  try {
+    connect = exec(
+      'boundary connect' +
+        ' -target-id=' +
+        targetId +
+        ' -exec /usr/bin/ssh --' +
+        ' -l ' +
+        process.env.E2E_SSH_USER +
+        ' -i ' +
+        process.env.E2E_SSH_KEY_PATH +
+        ' -o UserKnownHostsFile=/dev/null' +
+        ' -o StrictHostKeyChecking=no' +
+        ' -o IdentitiesOnly=yes' + // forces the use of the provided key
+        ' -p {{boundary.port}}' +
+        ' {{boundary.ip}}'
+    );
+  } catch (e) {
+    console.log(`${e.stderr}`);
+  }
+  return connect;
+};
+
+/**
+ * Uses the boundary CLI to delete the specified organization
+ * @param {string} orgId ID of the organization to be deleted
+ */
+exports.deleteOrg = async (orgId) => {
+  try {
+    exec('boundary scopes delete -id=' + orgId);
+  } catch (e) {
+    console.log(`${e.stderr}`);
+  }
+};
diff --git a/ui/admin/tests/e2e/helpers/boundary-ui.js b/ui/admin/tests/e2e/helpers/boundary-ui.js
index aa9cf59bc..14dbc37ab 100644
--- a/ui/admin/tests/e2e/helpers/boundary-ui.js
+++ b/ui/admin/tests/e2e/helpers/boundary-ui.js
@@ -167,6 +167,36 @@ exports.createNewTarget = async (page) => {
   return targetName;
 };
 
+/**
+ * Uses the UI to create a new target with address. Assumes you have selected the desired project.
+ * @param {Page} page Playwright page object
+ * @returns Name of the target
+ */
+exports.createNewTargetWithAddress = async (page) => {
+  const targetName = 'Target ' + nanoid();
+  await page
+    .getByRole('navigation', { name: 'Resources' })
+    .getByRole('link', { name: 'Targets' })
+    .click();
+  await page.getByRole('link', { name: 'New' }).click();
+  await page.getByLabel('Name').fill(targetName);
+  await page.getByLabel('Description').fill('This is an automated test');
+  await page.getByLabel('Target Address').fill(process.env.E2E_TARGET_IP);
+  await page.getByLabel('Default Port').fill(process.env.E2E_SSH_PORT);
+  await page.getByRole('button', { name: 'Save' }).click();
+  await expect(
+    page.getByRole('alert').getByText('Success', { exact: true })
+  ).toBeVisible();
+  await page.getByRole('button', { name: 'Dismiss' }).click();
+  await expect(
+    page
+      .getByRole('navigation', { name: 'breadcrumbs' })
+      .getByRole('link', { name: targetName })
+  ).toBeVisible();
+
+  return targetName;
+};
+
 /**
  * Uses the UI to add a host source to a target. Assume you have selected the desired target.
  * @param {Page} page Playwright page object
@@ -190,3 +220,32 @@ exports.addHostSourceToTarget = async (page, hostSourceName) => {
   await page.getByRole('button', { name: 'Dismiss' }).click();
   await expect(page.getByRole('link', { name: hostSourceName })).toBeVisible();
 };
+
+/**
+ * Uses the UI to navigate to Sessions and waits for the session to appear.
+ * @param {Page} page Playwright page object
+ * @param {string} targetName Name of the target associated with the session
+ */
+exports.waitForSessionToBeVisible = async (page, targetName) => {
+  await page
+    .getByRole('navigation', { name: 'Resources' })
+    .getByRole('link', { name: 'Sessions' })
+    .click();
+  let i = 0;
+  let sessionIsVisible = false;
+  do {
+    i = i + 1;
+    sessionIsVisible = await page
+      .getByRole('cell', { name: targetName })
+      .isVisible();
+    if (sessionIsVisible) {
+      break;
+    }
+    await page.getByRole('button', { name: 'Refresh' }).click();
+    await expect(page.getByRole('button', { name: 'Refresh' })).toBeEnabled();
+  } while (i < 5);
+
+  if (!sessionIsVisible) {
+    throw new Error('Session is not visible');
+  }
+};
diff --git a/ui/admin/tests/e2e/tests/target.spec.js b/ui/admin/tests/e2e/tests/target.spec.js
index cc790df20..abee22033 100644
--- a/ui/admin/tests/e2e/tests/target.spec.js
+++ b/ui/admin/tests/e2e/tests/target.spec.js
@@ -4,12 +4,14 @@
  */
 
 /* eslint-disable no-undef */
-const { test, expect } = require('@playwright/test');
-const { exec, execSync } = require('child_process');
+const { test } = require('@playwright/test');
+const { execSync } = require('child_process');
 const { checkEnv, authenticatedState } = require('../helpers/general');
 const {
   authenticateBoundaryCli,
   checkBoundaryCli,
+  connectToTarget,
+  deleteOrg,
 } = require('../helpers/boundary-cli');
 const {
   createNewOrg,
@@ -18,6 +20,8 @@ const {
   createNewHostSet,
   createNewHostInHostSet,
   createNewTarget,
+  createNewTargetWithAddress,
+  waitForSessionToBeVisible,
   addHostSourceToTarget,
 } = require('../helpers/boundary-ui');
 
@@ -34,10 +38,12 @@ test.beforeAll(async () => {
   await checkBoundaryCli();
 });
 
-test('Verify session created then cancel the session', async ({ page }) => {
+test('Verify session created to target with host, then cancel the session', async ({
+  page,
+}) => {
   await page.goto('/');
-
-  var connect;
+  let org;
+  let connect;
   try {
     const orgName = await createNewOrg(page);
     const projectName = await createNewProject(page);
@@ -49,7 +55,7 @@ test('Verify session created then cancel the session', async ({ page }) => {
 
     await authenticateBoundaryCli();
     const orgs = JSON.parse(execSync('boundary scopes list -format json'));
-    const org = orgs.items.filter((obj) => obj.name == orgName)[0];
+    org = orgs.items.filter((obj) => obj.name == orgName)[0];
     const projects = JSON.parse(
       execSync('boundary scopes list -format json -scope-id ' + org.id)
     );
@@ -59,50 +65,54 @@ test('Verify session created then cancel the session', async ({ page }) => {
     );
     const target = targets.items.filter((obj) => obj.name == targetName)[0];
 
-    connect = exec(
-      'boundary connect' +
-        ' -target-id=' +
-        target.id +
-        ' -exec /usr/bin/ssh --' +
-        ' -l ' +
-        process.env.E2E_SSH_USER +
-        ' -i ' +
-        process.env.E2E_SSH_KEY_PATH +
-        ' -o UserKnownHostsFile=/dev/null' +
-        ' -o StrictHostKeyChecking=no' +
-        ' -o IdentitiesOnly=yes' + // forces the use of the provided key
-        ' -p {{boundary.port}}' +
-        ' {{boundary.ip}}'
-    );
-
-    await page
-      .getByRole('navigation', { name: 'Resources' })
-      .getByRole('link', { name: 'Sessions' })
-      .click();
-    let i = 0;
-    let sessionIsVisible = false;
-    do {
-      i = i + 1;
-      sessionIsVisible = await page
-        .getByRole('cell', { name: targetName })
-        .isVisible();
-      if (sessionIsVisible) {
-        break;
-      }
-      await page.getByRole('button', { name: 'Refresh' }).click();
-      await expect(page.getByRole('button', { name: 'Refresh' })).toBeEnabled();
-    } while (i < 5);
-
-    if (!sessionIsVisible) {
-      throw new Error('Session is not visible');
-    }
-
+    connect = await connectToTarget(target.id);
+    await waitForSessionToBeVisible(page, targetName);
     await page
       .getByRole('cell', { name: targetName })
       .locator('..')
       .getByRole('button', { name: 'Cancel' })
       .click();
   } finally {
+    await deleteOrg(org.id);
+    // End `boundary connect` process
+    if (connect) {
+      connect.kill('SIGTERM');
+    }
+  }
+});
+
+test('Verify session created to target with address, then cancel the session', async ({
+  page,
+}) => {
+  await page.goto('/');
+  let org;
+  let connect;
+  try {
+    const orgName = await createNewOrg(page);
+    const projectName = await createNewProject(page);
+    const targetName = await createNewTargetWithAddress(page);
+
+    await authenticateBoundaryCli();
+    const orgs = JSON.parse(execSync('boundary scopes list -format json'));
+    org = orgs.items.filter((obj) => obj.name == orgName)[0];
+    const projects = JSON.parse(
+      execSync('boundary scopes list -format json -scope-id ' + org.id)
+    );
+    const project = projects.items.filter((obj) => obj.name == projectName)[0];
+    const targets = JSON.parse(
+      execSync('boundary targets list -format json -scope-id ' + project.id)
+    );
+    const target = targets.items.filter((obj) => obj.name == targetName)[0];
+
+    connect = await connectToTarget(target.id);
+    await waitForSessionToBeVisible(page, targetName);
+    await page
+      .getByRole('cell', { name: targetName })
+      .locator('..')
+      .getByRole('button', { name: 'Cancel' })
+      .click();
+  } finally {
+    await deleteOrg(org.id);
     // End `boundary connect` process
     if (connect) {
       connect.kill('SIGTERM');