diff --git a/tests/integration/content-aware-crop.test.ts b/tests/integration/content-aware-crop.test.ts
new file mode 100644
index 00000000..1d50f253
--- /dev/null
+++ b/tests/integration/content-aware-crop.test.ts
@@ -0,0 +1,230 @@
+/**
+ * Integration tests for the content-aware-crop AI tool (/api/v1/tools/content-aware-crop).
+ *
+ * This tool uses async processing: valid requests return 202 with a jobId,
+ * and the result is delivered via SSE. The Python sidecar is not available
+ * in the test environment, so the route returns 501 (not installed).
+ * Validation paths are always testable regardless of sidecar availability.
+ */
+
+import { readFileSync } from "node:fs";
+import { join } from "node:path";
+import { afterAll, beforeAll, describe, expect, it } from "vitest";
+import { buildTestApp, createMultipartPayload, loginAsAdmin, type TestApp } from "./test-server.js";
+
+const FIXTURES = join(__dirname, "..", "fixtures");
+const PNG = readFileSync(join(FIXTURES, "test-200x150.png"));
+
+let testApp: TestApp;
+let app: TestApp["app"];
+let adminToken: string;
+
+beforeAll(async () => {
+  testApp = await buildTestApp();
+  app = testApp.app;
+  adminToken = await loginAsAdmin(app);
+}, 30_000);
+
+afterAll(async () => {
+  await testApp.cleanup();
+}, 10_000);
+
+describe("Content-Aware Crop", () => {
+  // -- Processing (sidecar-dependent) ------------------------------------
+
+  it("returns 501 when AI sidecar is not installed", async () => {
+    const { body, contentType } = createMultipartPayload([
+      { name: "file", filename: "test.png", contentType: "image/png", content: PNG },
+      {
+        name: "settings",
+        content: JSON.stringify({
+          extendTop: 100,
+          extendRight: 0,
+          extendBottom: 100,
+          extendLeft: 0,
+        }),
+      },
+    ]);
+
+    const res = await app.inject({
+      method: "POST",
+      url: "/api/v1/tools/content-aware-crop",
+      headers: {
+        authorization: `Bearer ${adminToken}`,
+        "content-type": contentType,
+      },
+      body,
+    });
+
+    expect([202, 501]).toContain(res.statusCode);
+    if (res.statusCode === 501) {
+      const json = JSON.parse(res.body);
+      expect(json.code).toBe("FEATURE_NOT_INSTALLED");
+    }
+  }, 60_000);
+
+  // -- Validation (always testable) --------------------------------------
+
+  it("returns 400 when no image is provided", async () => {
+    const { body, contentType } = createMultipartPayload([
+      {
+        name: "settings",
+        content: JSON.stringify({ extendTop: 100, extendRight: 0, extendBottom: 0, extendLeft: 0 }),
+      },
+    ]);
+
+    const res = await app.inject({
+      method: "POST",
+      url: "/api/v1/tools/content-aware-crop",
+      headers: {
+        authorization: `Bearer ${adminToken}`,
+        "content-type": contentType,
+      },
+      body,
+    });
+
+    // 400 when sidecar is available (validation runs), 501 when not (isToolInstalled check fires first)
+    expect([400, 501]).toContain(res.statusCode);
+    if (res.statusCode === 400) {
+      const json = JSON.parse(res.body);
+      expect(json.error).toMatch(/no image/i);
+    }
+  });
+
+  it("returns 400 when no settings are provided", async () => {
+    const { body, contentType } = createMultipartPayload([
+      { name: "file", filename: "test.png", contentType: "image/png", content: PNG },
+    ]);
+
+    const res = await app.inject({
+      method: "POST",
+      url: "/api/v1/tools/content-aware-crop",
+      headers: {
+        authorization: `Bearer ${adminToken}`,
+        "content-type": contentType,
+      },
+      body,
+    });
+
+    // Without settings, defaults apply: all extends = 0 => "at least one direction" error
+    // But 501 fires first if sidecar is not installed
+    expect([400, 501]).toContain(res.statusCode);
+    if (res.statusCode === 400) {
+      const json = JSON.parse(res.body);
+      expect(json.error).toMatch(/at least one extend direction/i);
+    }
+  });
+
+  it("returns 400 when all extensions are zero", async () => {
+    const { body, contentType } = createMultipartPayload([
+      { name: "file", filename: "test.png", contentType: "image/png", content: PNG },
+      {
+        name: "settings",
+        content: JSON.stringify({ extendTop: 0, extendRight: 0, extendBottom: 0, extendLeft: 0 }),
+      },
+    ]);
+
+    const res = await app.inject({
+      method: "POST",
+      url: "/api/v1/tools/content-aware-crop",
+      headers: {
+        authorization: `Bearer ${adminToken}`,
+        "content-type": contentType,
+      },
+      body,
+    });
+
+    expect([400, 501]).toContain(res.statusCode);
+    if (res.statusCode === 400) {
+      const json = JSON.parse(res.body);
+      expect(json.error).toMatch(/at least one extend direction/i);
+    }
+  });
+
+  it("returns 400 with negative extension values", async () => {
+    const { body, contentType } = createMultipartPayload([
+      { name: "file", filename: "test.png", contentType: "image/png", content: PNG },
+      {
+        name: "settings",
+        content: JSON.stringify({
+          extendTop: -10,
+          extendRight: -5,
+          extendBottom: -20,
+          extendLeft: -15,
+        }),
+      },
+    ]);
+
+    const res = await app.inject({
+      method: "POST",
+      url: "/api/v1/tools/content-aware-crop",
+      headers: {
+        authorization: `Bearer ${adminToken}`,
+        "content-type": contentType,
+      },
+      body,
+    });
+
+    expect([400, 501]).toContain(res.statusCode);
+    if (res.statusCode === 400) {
+      const json = JSON.parse(res.body);
+      expect(json.error).toMatch(/invalid settings/i);
+    }
+  });
+
+  it("accepts valid request format (202 or 501)", async () => {
+    const { body, contentType } = createMultipartPayload([
+      { name: "file", filename: "test.png", contentType: "image/png", content: PNG },
+      {
+        name: "settings",
+        content: JSON.stringify({
+          extendTop: 100,
+          extendRight: 0,
+          extendBottom: 100,
+          extendLeft: 0,
+        }),
+      },
+    ]);
+
+    const res = await app.inject({
+      method: "POST",
+      url: "/api/v1/tools/content-aware-crop",
+      headers: {
+        authorization: `Bearer ${adminToken}`,
+        "content-type": contentType,
+      },
+      body,
+    });
+
+    expect([202, 501]).toContain(res.statusCode);
+    if (res.statusCode === 202) {
+      const json = JSON.parse(res.body);
+      expect(json.jobId).toBeDefined();
+      expect(json.async).toBe(true);
+    }
+  }, 60_000);
+
+  it("rejects unauthenticated requests (401)", async () => {
+    const { body, contentType } = createMultipartPayload([
+      { name: "file", filename: "test.png", contentType: "image/png", content: PNG },
+      {
+        name: "settings",
+        content: JSON.stringify({
+          extendTop: 50,
+          extendRight: 50,
+          extendBottom: 50,
+          extendLeft: 50,
+        }),
+      },
+    ]);
+
+    const res = await app.inject({
+      method: "POST",
+      url: "/api/v1/tools/content-aware-crop",
+      headers: { "content-type": contentType },
+      body,
+    });
+
+    expect(res.statusCode).toBe(401);
+  });
+});