diff --git a/ui-tests/jupyter_server_test_config.py b/ui-tests/jupyter_server_test_config.py
index 86fd4353..40174569 100644
--- a/ui-tests/jupyter_server_test_config.py
+++ b/ui-tests/jupyter_server_test_config.py
@@ -14,5 +14,7 @@
 c: Any
 configure_jupyter_server(c)  # noqa
 
+c.FileContentsManager.delete_to_trash = False
+
 # Uncomment to set server log level to debug level
 # c.ServerApp.log_level = "DEBUG"
diff --git a/ui-tests/tests/chat.spec.ts b/ui-tests/tests/chat.spec.ts
new file mode 100644
index 00000000..91bda7f4
--- /dev/null
+++ b/ui-tests/tests/chat.spec.ts
@@ -0,0 +1,145 @@
+/*
+ * Copyright (c) Jupyter Development Team.
+ * Distributed under the terms of the Modified BSD License.
+ */
+
+import { expect, IJupyterLabPageFixture, test } from '@jupyterlab/galata';
+import type { User } from '@jupyterlab/services';
+import type { Locator } from '@playwright/test';
+
+const openPanel = async (page: IJupyterLabPageFixture): Promise<Locator> => {
+  const panel = page.locator('.jp-SidePanel.jp-collab-chat-sidepanel');
+
+  if (!(await panel?.isVisible())) {
+    const chatIcon = page.getByTitle('Jupyter Chat');
+    await chatIcon.click();
+    await expect(panel).toBeVisible();
+  }
+  return panel.first();
+};
+
+test.describe('Initialization', () => {
+  test('should contain the chat panel icon', async ({ page }) => {
+    const chatIcon = page.getByTitle('Jupyter Chat');
+    expect(chatIcon).toHaveCount(1);
+    expect(await chatIcon.screenshot()).toMatchSnapshot(
+      'chat_icon.png'
+    );
+  });
+
+  test('chat panel should contain a toolbar', async ({ page }) => {
+    const panel = await openPanel(page);
+    const toolbar = panel.locator('.jp-SidePanel-toolbar');
+    await expect(toolbar).toHaveCount(1);
+
+    const items = toolbar.locator('.jp-Toolbar-item');
+    await expect(items).toHaveCount(2);
+    await expect(items.first()).toHaveClass(/.jp-collab-chat-add/);
+    await expect(items.last()).toHaveClass(/.jp-collab-chat-open/);
+  });
+
+  test('chat panel should not contain a chat at init', async ({ page }) => {
+    const panel = await openPanel(page);
+    const content = panel.locator('.jp-SidePanel-content');
+    await expect(content).toBeEmpty();
+  });
+})
+
+test.describe('Chat creation', () => {
+  let panel: Locator;
+  let dialog: Locator;
+
+  test.beforeEach(async ({ page }) => {
+    panel = await openPanel(page);
+    const addButton = panel.locator(
+      '.jp-SidePanel-toolbar .jp-Toolbar-item.jp-collab-chat-add'
+    );
+    await addButton.click();
+
+    dialog = page.locator('.jp-Dialog');
+    await dialog.waitFor();
+  });
+
+  test('should create a chat', async ({ page }) => {
+    await dialog.locator('input[type="text"]').type('chat-test');
+    await dialog.getByRole('button').getByText('Ok').click();
+    expect(await page.filebrowser.contents.fileExists('chat-test.chat')).toBeTruthy();
+
+    const chatTitle = panel.locator('.jp-SidePanel-content .jp-AccordionPanel-title');
+    await expect(chatTitle).toHaveCount(1);
+    await expect(chatTitle.locator('.lm-AccordionPanel-titleLabel')).toHaveText(
+      'chat-test'
+    );
+  });
+
+  test('should create an untitled file if no name is provided', async ({ page }) => {
+    await dialog.getByRole('button').getByText('Ok').click();
+    expect(await page.filebrowser.contents.fileExists('untitled.chat')).toBeTruthy();
+
+    const chatTitle = panel.locator('.jp-SidePanel-content .jp-AccordionPanel-title');
+    await expect(chatTitle).toHaveCount(1);
+    await expect(chatTitle.locator('.lm-AccordionPanel-titleLabel')).toHaveText(
+      'untitled'
+    );
+  });
+
+  test('should not create a chat if dialog is cancelled', async ({ page }) => {
+    await dialog.getByRole('button').getByText('Cancel').click();
+
+    const content = panel.locator('.jp-SidePanel-content');
+    await expect(content).toBeEmpty();
+  });
+})
+
+test.describe('Opening/closing chat', () => {
+  const name = 'my-chat';
+  let panel: Locator;
+  let select: Locator;
+
+  test.beforeEach(async ({ page }) => {
+    await page.filebrowser.contents.uploadContent('{}', 'text', `${name}.chat`);
+  });
+
+  test.afterEach(async ({ page }) => {
+    await page.filebrowser.contents.deleteFile( `${name}.chat`);
+  });
+
+  test('should list existing chat', async ({ page }) => {
+    // reload to update the chat list
+    // FIX: add listener on file creation
+    await page.reload();
+    panel = await openPanel(page);
+    select = panel.locator(
+      '.jp-SidePanel-toolbar .jp-Toolbar-item.jp-collab-chat-open select'
+    );
+
+    for (let i=0; i< await select.locator('option').count(); i++) {
+      console.log(await select.locator('option').nth(i).textContent());
+    }
+    await expect(select.locator('option')).toHaveCount(2);
+    await expect(select.locator('option').last()).toHaveText(name);
+  });
+
+  test('should open an existing chat and close it', async ({ page }) => {
+    // reload to update the chat list
+    // FIX: add listener on file creation
+    await page.reload();
+    panel = await openPanel(page);
+    select = panel.locator(
+      '.jp-SidePanel-toolbar .jp-Toolbar-item.jp-collab-chat-open select'
+    );
+
+    await select.selectOption(name);
+
+    const chatTitle = panel.locator('.jp-SidePanel-content .jp-AccordionPanel-title');
+    await expect(chatTitle).toHaveCount(1);
+    await expect(chatTitle.locator('.lm-AccordionPanel-titleLabel')).toHaveText(
+      name
+    );
+
+    await page.pause();
+    await chatTitle.getByRole('button').click();
+    await page.pause();
+    await expect(chatTitle).toHaveCount(0);
+  });
+});
diff --git a/ui-tests/tests/chat.spec.ts-snapshots/chat-icon-linux.png b/ui-tests/tests/chat.spec.ts-snapshots/chat-icon-linux.png
new file mode 100644
index 00000000..76b5d4e0
Binary files /dev/null and b/ui-tests/tests/chat.spec.ts-snapshots/chat-icon-linux.png differ