diff --git a/tests/e2e/content-aware-crop.spec.ts b/tests/e2e/content-aware-crop.spec.ts
new file mode 100644
index 00000000..9c48b3d1
--- /dev/null
+++ b/tests/e2e/content-aware-crop.spec.ts
@@ -0,0 +1,169 @@
+import path from "node:path";
+import { expect, isAiSidecarRunning, test } from "./helpers";
+
+function fixturePath(name: string): string {
+  return path.join(process.cwd(), "tests", "fixtures", name);
+}
+
+async function uploadFile(page: import("@playwright/test").Page, filePath: string) {
+  const fileChooserPromise = page.waitForEvent("filechooser");
+  const dropzone = page.locator("[class*='border-dashed']").first();
+  await dropzone.click();
+  const fileChooser = await fileChooserPromise;
+  await fileChooser.setFiles(filePath);
+  await page.waitForTimeout(500);
+}
+
+test.describe("Content-Aware Crop", () => {
+  // ── Standalone /content-aware-crop route ────────────────────────────
+
+  test("standalone /content-aware-crop route loads", async ({ loggedInPage: page }) => {
+    await page.goto("/content-aware-crop");
+
+    await expect(page.getByText("Tool not found")).not.toBeVisible();
+    await expect(page.getByText("Content-Aware Crop")).toBeVisible();
+    await expect(page.getByText("Extend to aspect ratio")).toBeVisible();
+    await expect(page.getByText("Extend by (pixels)")).toBeVisible();
+  });
+
+  test("standalone submit disabled without file", async ({ loggedInPage: page }) => {
+    await page.goto("/content-aware-crop");
+    await expect(page.getByTestId("content-aware-crop-submit")).toBeDisabled();
+  });
+
+  test("standalone submit disabled when all extensions are zero", async ({
+    loggedInPage: page,
+  }) => {
+    await page.goto("/content-aware-crop");
+    await uploadFile(page, fixturePath("test-200x150.png"));
+
+    await expect(page.getByTestId("content-aware-crop-submit")).toBeDisabled();
+  });
+
+  test("standalone submit enables with extension set", async ({ loggedInPage: page }) => {
+    await page.goto("/content-aware-crop");
+    await uploadFile(page, fixturePath("test-200x150.png"));
+
+    await page.locator("#cac-top").fill("50");
+
+    await expect(page.getByTestId("content-aware-crop-submit")).toBeEnabled();
+  });
+
+  test("standalone aspect ratio preset fills extension values", async ({ loggedInPage: page }) => {
+    await page.goto("/content-aware-crop");
+    await uploadFile(page, fixturePath("test-200x150.png"));
+
+    await page.waitForTimeout(500);
+    await page.getByRole("button", { name: "16:9" }).click();
+
+    const topInput = page.locator("#cac-top");
+    const rightInput = page.locator("#cac-right");
+
+    const topVal = Number(await topInput.inputValue());
+    const rightVal = Number(await rightInput.inputValue());
+
+    expect(topVal > 0 || rightVal > 0).toBe(true);
+    await expect(page.getByTestId("content-aware-crop-submit")).toBeEnabled();
+  });
+
+  test("standalone shows new size display", async ({ loggedInPage: page }) => {
+    await page.goto("/content-aware-crop");
+    await uploadFile(page, fixturePath("test-200x150.png"));
+
+    await page.waitForTimeout(500);
+    await page.locator("#cac-top").fill("50");
+    await page.locator("#cac-bottom").fill("50");
+
+    await expect(page.getByText(/New size: \d+ x \d+/)).toBeVisible();
+  });
+
+  // ── Crop tool Content-Aware tab (/crop) ─────────────────────────────
+
+  test("crop page shows Standard and Content-Aware tabs", async ({ loggedInPage: page }) => {
+    await page.goto("/crop");
+    await uploadFile(page, fixturePath("test-200x150.png"));
+
+    await expect(page.getByRole("button", { name: "Standard" })).toBeVisible();
+    await expect(page.getByRole("button", { name: "Content-Aware" })).toBeVisible();
+  });
+
+  test("Content-Aware tab hides crop-specific controls", async ({ loggedInPage: page }) => {
+    await page.goto("/crop");
+    await uploadFile(page, fixturePath("test-200x150.png"));
+
+    await expect(page.getByText("Position & Size")).toBeVisible();
+
+    await page.getByRole("button", { name: "Content-Aware" }).click();
+
+    await expect(page.getByText("Position & Size")).not.toBeVisible();
+    await expect(page.getByText("Extend to aspect ratio")).toBeVisible();
+    await expect(page.getByText("Extend by (pixels)")).toBeVisible();
+  });
+
+  test("switching back to Standard restores crop controls", async ({ loggedInPage: page }) => {
+    await page.goto("/crop");
+    await uploadFile(page, fixturePath("test-200x150.png"));
+
+    await page.getByRole("button", { name: "Content-Aware" }).click();
+    await expect(page.getByText("Extend to aspect ratio")).toBeVisible();
+
+    await page.getByRole("button", { name: "Standard" }).click();
+    await expect(page.getByText("Position & Size")).toBeVisible();
+    await expect(page.getByText("Extend to aspect ratio")).not.toBeVisible();
+  });
+
+  test("Content-Aware tab aspect ratio presets set extensions", async ({ loggedInPage: page }) => {
+    await page.goto("/crop");
+    await uploadFile(page, fixturePath("test-200x150.png"));
+
+    await page.getByRole("button", { name: "Content-Aware" }).click();
+    await page.waitForTimeout(300);
+
+    await page.getByRole("button", { name: "1:1" }).click();
+
+    const topInput = page.locator("#cac-crop-top").or(
+      page
+        .locator("input")
+        .filter({ has: page.locator("[id*='top']") })
+        .first(),
+    );
+    const extendInputs = page.locator("input[type='number']");
+    const values = await extendInputs.evaluateAll((els) =>
+      els.map((el) => Number((el as HTMLInputElement).value)),
+    );
+
+    const hasNonZero = values.some((v) => v > 0);
+    expect(hasNonZero).toBe(true);
+  });
+
+  test("Content-Aware submit button says Extend", async ({ loggedInPage: page }) => {
+    await page.goto("/crop");
+    await uploadFile(page, fixturePath("test-200x150.png"));
+
+    await page.getByRole("button", { name: "Content-Aware" }).click();
+
+    const submitBtn = page.getByTestId("crop-submit");
+    await expect(submitBtn).toHaveText(/Extend/);
+  });
+
+  // ── Processing (requires AI sidecar) ────────────────────────────────
+
+  test("processes image (AI sidecar required)", async ({ loggedInPage: page }) => {
+    await page.goto("/content-aware-crop");
+
+    if (!(await isAiSidecarRunning(page))) {
+      test.skip(true, "AI sidecar not running");
+    }
+
+    await uploadFile(page, fixturePath("test-200x150.png"));
+    await page.locator("#cac-top").fill("30");
+    await page.locator("#cac-bottom").fill("30");
+
+    await page.getByTestId("content-aware-crop-submit").click();
+
+    const download = page.getByTestId("content-aware-crop-download");
+    const error = page.getByText(/failed|not available|not installed|error/i);
+
+    await expect(download.or(error)).toBeVisible({ timeout: 300_000 });
+  });
+});