diff --git a/site/e2e/README.md b/site/e2e/README.md
index 291344a67c..315de9dd47 100644
--- a/site/e2e/README.md
+++ b/site/e2e/README.md
@@ -46,3 +46,11 @@ Enterprise tests require a license key to run.
 ```shell
 export CODER_E2E_ENTERPRISE_LICENSE=<license key>
 ```
+
+# Debugging tests
+
+To debug a test, it is more helpful to run it in `ui` mode.
+
+```
+pnpm playwright:test-ui
+```
diff --git a/site/e2e/api.ts b/site/e2e/api.ts
index 88f8666475..9bb8d62719 100644
--- a/site/e2e/api.ts
+++ b/site/e2e/api.ts
@@ -6,8 +6,12 @@ import { findSessionToken, randomName } from "./helpers";
 let currentOrgId: string;
 
 export const setupApiCalls = async (page: Page) => {
-  const token = await findSessionToken(page);
-  API.setSessionToken(token);
+  try {
+    const token = await findSessionToken(page);
+    API.setSessionToken(token);
+  } catch {
+    // If this fails, we have an unauthenticated client.
+  }
   API.setHost(`http://127.0.0.1:${coderPort}`);
 };
 
diff --git a/site/e2e/global.setup.ts b/site/e2e/global.setup.ts
index fd37b29ea5..b99c461308 100644
--- a/site/e2e/global.setup.ts
+++ b/site/e2e/global.setup.ts
@@ -1,10 +1,19 @@
 import { expect, test } from "@playwright/test";
+import { hasFirstUser } from "api/api";
 import { Language } from "pages/CreateUserPage/CreateUserForm";
+import { setupApiCalls } from "./api";
 import * as constants from "./constants";
 import { storageState } from "./playwright.config";
 
 test("setup deployment", async ({ page }) => {
   await page.goto("/", { waitUntil: "domcontentloaded" });
+  await setupApiCalls(page);
+  const exists = await hasFirstUser();
+  // First user already exists, abort early. All tests execute this as a dependency,
+  // if you run multiple tests in the UI, this will fail unless we check this.
+  if (exists) {
+    return;
+  }
 
   // Setup first user
   await page.getByLabel(Language.usernameLabel).fill(constants.username);
diff --git a/site/package.json b/site/package.json
index 016f0bdafa..24ba4d5262 100644
--- a/site/package.json
+++ b/site/package.json
@@ -16,6 +16,7 @@
     "lint:types": "tsc -p .",
     "playwright:install": "playwright install --with-deps chromium",
     "playwright:test": "playwright test --config=e2e/playwright.config.ts",
+    "playwright:test-ui": "playwright test --config=e2e/playwright.config.ts --ui $([[ \"$CODER\" == \"true\" ]] && echo --ui-port=7500 --ui-host=0.0.0.0)",
     "gen:provisioner": "protoc --plugin=./node_modules/.bin/protoc-gen-ts_proto --ts_proto_out=./e2e/ --ts_proto_opt=outputJsonMethods=false,outputEncodeMethods=encode-no-creation,outputClientImpl=false,nestJs=false,outputPartialMethods=false,fileSuffix=Generated,suffix=hey -I ../provisionersdk/proto ../provisionersdk/proto/provisioner.proto && pnpm exec prettier --ignore-path '/dev/null' --cache --write './e2e/provisionerGenerated.ts'",
     "storybook": "STORYBOOK=true storybook dev -p 6006",
     "storybook:build": "storybook build",