diff --git a/lumigator/frontend/e2e/datasets.spec.ts b/lumigator/frontend/e2e/datasets.spec.ts
index 0d131abfd..ff2aa1580 100644
--- a/lumigator/frontend/e2e/datasets.spec.ts
+++ b/lumigator/frontend/e2e/datasets.spec.ts
@@ -1,47 +1,123 @@
 import { test, expect } from '@playwright/test'
-import path from 'path'
+import { log } from 'console';
+import path from 'path';
+import fs from 'fs';
 
 // get the sample dataset absolute file path
-const currentDir = path.dirname(new URL(import.meta.url).pathname)
+const currentDir = path.dirname(new URL(import.meta.url).pathname);
 const sampleDatasetFilePath = path.resolve(
   currentDir,
-  '../../sample_data/summarization/dialogsum_exc.csv',
-)
+  '../../sample_data/summarization/dialogsum_mini_no_gt.csv'
+);
 
-test('successfully uploads a dataset', async ({ page }) => {
-  await page.goto('/')
+// Create a unique file name by appending a timestamp.
+const timestamp = Date.now();
+const dynamicFileName = `dialogsum_mini_no_gt_${timestamp}.csv`;
+let submittedFileName = dynamicFileName;
 
-  // find & click the provide dataset button and capture the system file chooser dialog
-  const fileChooserPromise = page.waitForEvent('filechooser')
-  const button = page.getByRole('button', { name: 'Provide Dataset' })
-  await button.click()
-  const fileChooser = await fileChooserPromise
 
-  // choose the sample dataset file from the file chooser dialog
-  await fileChooser.setFiles(sampleDatasetFilePath)
+test('Launch a GT workflow with unique file and fail early on job failure', async ({ page }) => {
+  // Increase test timeout to 10 minutes.
+  test.setTimeout(600000);
+  await page.goto('/');
 
-  // click the upload button from the confirmation modal
-  const uploadButton = page.getByRole('button', { name: 'Upload' })
-  await uploadButton.click()
+  // Trigger file chooser by clicking "Provide Dataset".
+  const fileChooserPromise = page.waitForEvent('filechooser');
+  const provideDatasetButton = page.getByRole('button', { name: 'Provide Dataset' });
+  await provideDatasetButton.click();
+  const fileChooser = await fileChooserPromise;
 
-  // wait for the api requests to upload the file and refetch the datasets
+  const fileBuffer = fs.readFileSync(sampleDatasetFilePath);
+  await fileChooser.setFiles({
+    name: dynamicFileName,
+    mimeType: 'text/csv',
+    buffer: fileBuffer,
+  });
+
+  // Click the "Upload" button from the confirmation modal.
+  const uploadButton = page.getByRole('button', { name: 'Upload' });
+  await uploadButton.click();
+
+  // Wait for the API requests for upload and refresh.
   const [response] = await Promise.all([
     page.waitForResponse(
       (response) =>
         response.url().includes('datasets') &&
         response.status() === 201 &&
-        response.request().method() === 'POST',
+        response.request().method() === 'POST'
     ),
     page.waitForRequest(
-      (request) => request.url().includes('datasets') && request.method() === 'GET',
+      (request) => request.url().includes('datasets') && request.method() === 'GET'
     ),
-  ])
+  ]);
 
-  // get the returned filename and id from the api response
-  const { id, filename } = await response.json()
+  // Extract returned dataset id and filename from the API response.
+  const { id, filename } = await response.json();
 
-  // wait for the new table row with the new dataset id and filename to be rendered, (ids are shortened so we only check the first 20 characters)
+  // Wait for the new dataset row to appear in the table.
   await expect(
-    page.locator(`table tr:has(td:text("${id.slice(0, 20)}")):has(td:text("${filename}"))`),
-  ).toBeVisible()
-})
+    page.locator(`table tr:has(td:text("${id.slice(0, 20)}")):has(td:text("${filename}"))`)
+  ).toBeVisible();
+
+  // Click the dataset row (using the unique submittedFileName).
+  const datasetRow = page.locator('tr').filter({ hasText: submittedFileName }).first();
+  await expect(datasetRow).toBeVisible({ timeout: 5000 });
+  await datasetRow.click();
+
+  // Wait for the sidebar (with class "sliding-panel") to appear.
+  const sidebar = page.locator('.sliding-panel');
+  await expect(sidebar).toBeVisible({ timeout: 5000 });
+
+  // In the sidebar, click the "Generate Ground Truth" button.
+  const generateGtButton = sidebar.getByRole('button', { name: 'Generate Ground Truth' });
+  await expect(generateGtButton).toBeVisible({ timeout: 5000 });
+  await generateGtButton.click();
+
+  // Wait for the popup to appear (identified by its ".popup" class).
+  const popupContainer = page.locator('.popup');
+  await expect(popupContainer).toBeVisible({ timeout: 5000 });
+
+  // Click "Start Generating" and wait for the API to create the job.
+  const [jobResponse] = await Promise.all([
+    page.waitForResponse(
+      (res) =>
+        res.url().includes('/jobs') &&
+        res.request().method() === 'POST' &&
+        res.status() === 201
+    ),
+    popupContainer.getByRole('button', { name: 'Start Generating' }).click(),
+  ]);
+
+  // Extract the job ID from the API response.
+  const jobData = await jobResponse.json();
+  const jobId = jobData.id; // e.g., "712afa3f-ee81-41c0-8f1b-8939c2bf0ee4"
+
+  // Switch to the "Ground Truth Jobs" tab.
+  const groundTruthJobsTab = page.locator('button').filter({ hasText: 'Ground Truth Jobs' });
+  await groundTruthJobsTab.click();
+
+
+  await page.waitForFunction(
+    (fileName) => {
+      const rows = Array.from(document.querySelectorAll('tr')).filter(row =>
+        (row.textContent || "").includes(fileName)
+      );
+      if (rows.length === 0) return false;
+      const lastRow = rows[rows.length - 1];
+      const statusEl = lastRow.querySelector('.p-tag-label');
+      if (!statusEl || !(statusEl instanceof HTMLElement)) return false;
+      const status = statusEl.innerText.trim().toLowerCase();
+      if (status === 'failed') {
+          throw new Error('Job failed');
+      }
+      return status === 'succeeded';
+    },
+    submittedFileName,
+    { timeout: 600000 }
+  );
+
+  // Assert that the last row’s status is "succeeded".
+  const jobRows = page.locator(`tr:has(td:has-text("${submittedFileName}"))`);
+  const lastJobRow = jobRows.last();
+  await expect(lastJobRow.locator('.p-tag-label')).toHaveText(/succeeded/i);
+});