diff --git a/e2e/work-orders/pending-status-menu.spec.ts b/e2e/work-orders/pending-status-menu.spec.ts
new file mode 100644
index 00000000..90c1beca
--- /dev/null
+++ b/e2e/work-orders/pending-status-menu.spec.ts
@@ -0,0 +1,183 @@
+import { expect, test, type Page, type Route } from "@playwright/test";
+
+const FROZEN_NOW = "2026-08-19T15:00:00.000Z";
+
+const BOARD_ROW = {
+  id: 1,
+  woNumber: "WO-501",
+  workOrderType: 2,
+  siteCode: "STL-01",
+  locationName: "St. Louis HQ",
+  locationId: 10,
+  lifecycleStatusLabel: "In Progress",
+  scheduledDate: "2026-08-19",
+  dispatcherId: "1",
+  dispatcherName: "Pat Dispatcher",
+  pm: "HVAC",
+  rowVersion: "rv-1",
+};
+
+type Role = "Admin" | "Dispatcher";
+
+async function fulfillJson(route: Route, body: unknown) {
+  await route.fulfill({ status: 200, contentType: "application/json", body: JSON.stringify(body) });
+}
+
+async function mockApi(page: Page, role: Role, createPayloads: unknown[] = []) {
+  await page.clock.install({ time: new Date(FROZEN_NOW) });
+  await page.clock.resume();
+  await page.addInitScript(
+    (user) => {
+      localStorage.setItem("auth", JSON.stringify(user));
+      const style = document.createElement("style");
+      style.textContent = ".tsqd-parent-container { display: none !important; }";
+      document.documentElement.appendChild(style);
+    },
+    {
+      token: `wo-pending-${role.toLowerCase()}-e2e-token`,
+      expiration: "2030-01-01T00:00:00.000Z",
+      email: `${role.toLowerCase()}@seahavenind.com`,
+      userRoles: role,
+      phoneNumber: "5551234567",
+      fullname: `Work Order E2E ${role}`,
+      id: "1",
+    },
+  );
+
+  let row = { ...BOARD_ROW };
+  let createdRow: typeof BOARD_ROW | undefined;
+  await page.route(
+    (url) => url.pathname.startsWith("/api/"),
+    async (route) => {
+      const request = route.request();
+      const { pathname } = new URL(request.url());
+
+      if (pathname.includes("/workorders/board/search")) {
+        await fulfillJson(route, { items: [], totalCount: 0, page: 0, pageSize: 50 });
+        return;
+      }
+      if (pathname === "/api/workorders/board" && request.method() === "GET") {
+        await fulfillJson(route, {
+          weekStart: "2026-08-17",
+          weekEnd: "2026-08-21",
+          counts: { returned: createdRow ? 2 : 1, total: createdRow ? 2 : 1 },
+          unscheduled: createdRow ? [createdRow] : [],
+          scheduled: [row],
+        });
+        return;
+      }
+      if (pathname === "/api/workorders/board" && request.method() === "POST") {
+        createPayloads.push(request.postDataJSON());
+        createdRow = {
+          ...BOARD_ROW,
+          id: 900,
+          woNumber: "WO-900",
+          lifecycleStatusLabel: "Pending",
+          scheduledDate: "",
+          rowVersion: "rv-created",
+        };
+        await fulfillJson(route, { data: { id: 900, internalWONumber: "WO-900" } });
+        return;
+      }
+      if (pathname === "/api/workorders/1/board" && request.method() === "PATCH") {
+        const body = request.postDataJSON() as { field: string; value: string };
+        row = { ...row, lifecycleStatusLabel: body.value, rowVersion: "rv-2" };
+        await fulfillJson(route, row);
+        return;
+      }
+      if (pathname.includes("/locations/sites") || pathname.includes("/Contact/GetLocations")) {
+        await fulfillJson(route, {
+          data: [{ id: 10, name: "STL-01 · St. Louis, MO", siteCode: "STL-01", code: "STL-01" }],
+        });
+        return;
+      }
+      if (pathname === "/api/locations/10") {
+        await fulfillJson(route, {
+          data: {
+            id: 10,
+            name: "St. Louis HQ",
+            siteCode: "STL-01",
+            contact: "Pat Site",
+            phone: "3145550111",
+          },
+        });
+        return;
+      }
+      await fulfillJson(route, { data: [], items: [] });
+    },
+  );
+}
+
+async function expectManualTransitionWithoutPending(page: Page) {
+  const row = page.locator("#wo-row-1");
+  await expect(row.getByText("WO-501")).toBeVisible();
+  await row.getByRole("button", { name: "In Progress" }).click();
+
+  const menu = page.locator(".MuiPopover-paper").last();
+  await expect(menu.getByRole("button", { name: "Pending", exact: true })).toHaveCount(0);
+  await expect(menu.getByRole("button", { name: "On Site", exact: true })).toBeEnabled();
+  await menu.getByRole("button", { name: "On Site", exact: true }).click();
+
+  await expect(row.getByRole("button", { name: "On Site" })).toBeVisible();
+}
+
+test.describe("existing work order status menu", () => {
+  test.setTimeout(60_000);
+
+  test("Admin can choose a manual status but not Pending", async ({ page }) => {
+    await mockApi(page, "Admin");
+    await page.goto("/workorders");
+    await expect(page.getByRole("heading", { name: "Work Orders" })).toBeVisible({
+      timeout: 20_000,
+    });
+
+    await expectManualTransitionWithoutPending(page);
+  });
+
+  test("Dispatcher can choose a manual status but not Pending", async ({ page }) => {
+    await mockApi(page, "Dispatcher");
+    await page.goto("/workorders");
+    await expect(page.getByRole("heading", { name: "Work Orders" })).toBeVisible({
+      timeout: 20_000,
+    });
+
+    await expectManualTransitionWithoutPending(page);
+  });
+
+  test("Admin can select Pending for a new work order when Schedule On has no date", async ({
+    page,
+  }) => {
+    const createPayloads: unknown[] = [];
+    await mockApi(page, "Admin", createPayloads);
+    await page.goto("/workorders");
+    await expect(page.getByRole("heading", { name: "Work Orders" })).toBeVisible({
+      timeout: 20_000,
+    });
+    await page.getByRole("button", { name: "New WO" }).click();
+    await expect(page.getByRole("heading", { name: "Type & schedule" })).toBeVisible();
+    await expect(page.getByRole("button", { name: "Pick a date" })).toBeVisible();
+    await page.getByRole("button", { name: "Continue" }).click();
+
+    await page.getByRole("button", { name: /select site/i }).click();
+    await page
+      .getByRole("button", { name: /STL-01/ })
+      .last()
+      .click();
+    await page.getByRole("button", { name: "Continue" }).click();
+
+    await page.getByRole("button", { name: "Incomplete", exact: true }).last().click();
+    const menu = page.locator(".MuiPopover-paper").last();
+    await expect(menu.getByRole("button", { name: "Pending", exact: true })).toBeEnabled();
+    await menu.getByRole("button", { name: "Pending", exact: true }).click();
+    await expect(page.getByRole("button", { name: "Pending", exact: true })).toBeVisible();
+
+    await page.getByRole("button", { name: "Create work order" }).click();
+    await expect(page.getByRole("heading", { name: "Type & schedule" })).toBeHidden();
+    await expect
+      .poll(() => createPayloads)
+      .toEqual([expect.objectContaining({ lifecycleStatus: 2 })]);
+    const createdRow = page.locator("#wo-row-900");
+    await expect(createdRow.getByText("WO-900")).toBeVisible();
+    await expect(createdRow.getByRole("button", { name: "Pending" })).toBeVisible();
+  });
+});