diff --git a/src/app/api/oauth/cursor/auto-import/route.js b/src/app/api/oauth/cursor/auto-import/route.js
index 2a9eec8..f4487a9 100644
--- a/src/app/api/oauth/cursor/auto-import/route.js
+++ b/src/app/api/oauth/cursor/auto-import/route.js
@@ -1,4 +1,5 @@
 import { NextResponse } from "next/server";
+import { access, constants } from "fs/promises";
 import { homedir } from "os";
 import { join } from "path";
 import Database from "better-sqlite3";
@@ -12,9 +13,31 @@ export async function GET() {
     const platform = process.platform;
     let dbPath;
 
-    // Determine database path based on platform
     if (platform === "darwin") {
-      dbPath = join(homedir(), "Library/Application Support/Cursor/User/globalStorage/state.vscdb");
+      // macOS: probe multiple locations (standard + Insiders)
+      const userHome = homedir();
+      const candidateDbPaths = [
+        join(userHome, "Library/Application Support/Cursor/User/globalStorage/state.vscdb"),
+        join(userHome, "Library/Application Support/Cursor - Insiders/User/globalStorage/state.vscdb"),
+      ];
+
+      for (const path of candidateDbPaths) {
+        try {
+          await access(path, constants.R_OK);
+          dbPath = path;
+          break;
+        } catch {
+          // Continue probing next candidate.
+        }
+      }
+
+      if (!dbPath) {
+        return NextResponse.json({
+          found: false,
+          error:
+            "Cursor database not found in known macOS locations. Make sure Cursor IDE is installed and opened at least once.",
+        });
+      }
     } else if (platform === "linux") {
       dbPath = join(homedir(), ".config/Cursor/User/globalStorage/state.vscdb");
     } else if (platform === "win32") {
@@ -31,6 +54,12 @@ export async function GET() {
     try {
       db = new Database(dbPath, { readonly: true, fileMustExist: true });
     } catch (error) {
+      if (platform === "darwin") {
+        return NextResponse.json({
+          found: false,
+          error: `Found Cursor database at ${dbPath} but could not open it: ${error.message}`,
+        });
+      }
       return NextResponse.json({
         found: false,
         error: "Cursor database not found. Make sure Cursor IDE is installed and you are logged in.",
@@ -38,17 +67,58 @@ export async function GET() {
     }
 
     try {
-      // Extract tokens from database
+      const accessTokenKeys = [
+        "cursorAuth/accessToken",
+        "cursorAuth/token",
+      ];
+      const machineIdKeys = [
+        "storage.serviceMachineId",
+        "storage.machineId",
+        "telemetry.machineId",
+      ];
+      const desiredKeys = [...accessTokenKeys, ...machineIdKeys];
+
       const rows = db.prepare(
-        "SELECT key, value FROM itemTable WHERE key IN (?, ?)"
-      ).all("cursorAuth/accessToken", "storage.serviceMachineId");
+        `SELECT key, value FROM itemTable WHERE key IN (${desiredKeys.map(() => "?").join(",")})`
+      ).all(...desiredKeys);
+
+      const normalizeValue = (value) => {
+        if (typeof value !== "string") return value;
+        try {
+          const parsed = JSON.parse(value);
+          return typeof parsed === "string" ? parsed : value;
+        } catch {
+          return value;
+        }
+      };
 
       const tokens = {};
       for (const row of rows) {
-        if (row.key === "cursorAuth/accessToken") {
-          tokens.accessToken = row.value;
-        } else if (row.key === "storage.serviceMachineId") {
-          tokens.machineId = row.value;
+        if (accessTokenKeys.includes(row.key) && !tokens.accessToken) {
+          tokens.accessToken = normalizeValue(row.value);
+        } else if (machineIdKeys.includes(row.key) && !tokens.machineId) {
+          tokens.machineId = normalizeValue(row.value);
+        }
+      }
+
+      // Fuzzy fallback for newer/changed key names (macOS only, where the
+      // issue was originally reported; other platforms use exact keys).
+      if (platform === "darwin" && (!tokens.accessToken || !tokens.machineId)) {
+        const fallbackRows = db.prepare(
+          "SELECT key, value FROM itemTable WHERE key LIKE '%cursorAuth/%' OR key LIKE '%machineId%' OR key LIKE '%serviceMachineId%'"
+        ).all();
+
+        for (const row of fallbackRows) {
+          const key = row.key || "";
+          const value = normalizeValue(row.value);
+
+          if (!tokens.accessToken && key.toLowerCase().includes("accesstoken")) {
+            tokens.accessToken = value;
+          }
+
+          if (!tokens.machineId && key.toLowerCase().includes("machineid")) {
+            tokens.machineId = value;
+          }
         }
       }
 
diff --git a/tests/unit/oauth-cursor-auto-import.test.js b/tests/unit/oauth-cursor-auto-import.test.js
new file mode 100644
index 0000000..c5abe0d
--- /dev/null
+++ b/tests/unit/oauth-cursor-auto-import.test.js
@@ -0,0 +1,184 @@
+import { describe, it, expect, vi, beforeEach, afterEach } from "vitest";
+import * as fsPromises from "fs/promises";
+
+// Mock next/server
+vi.mock("next/server", () => ({
+  NextResponse: {
+    json: vi.fn((body, init) => ({
+      status: init?.status || 200,
+      body,
+      json: async () => body,
+    })),
+  },
+}));
+
+// Mock os
+vi.mock("os", () => ({
+  default: { homedir: vi.fn(() => "/mock/home") },
+  homedir: vi.fn(() => "/mock/home"),
+}));
+
+// Mock fs/promises
+vi.mock("fs/promises", () => ({
+  access: vi.fn(),
+  constants: { R_OK: 4 },
+}));
+
+// Shared mock db instance
+const mockDbInstance = {
+  prepare: vi.fn(),
+  close: vi.fn(),
+  __throwOnConstruct: false,
+};
+
+// Mock better-sqlite3 as a class so `new Database(...)` works
+vi.mock("better-sqlite3", () => ({
+  default: class MockDatabase {
+    constructor() {
+      if (mockDbInstance.__throwOnConstruct) {
+        throw new Error("SQLITE_CANTOPEN");
+      }
+      return mockDbInstance;
+    }
+  },
+}));
+
+// We need to dynamically import after mocks are registered
+let GET;
+
+describe("GET /api/oauth/cursor/auto-import", () => {
+  const originalPlatform = process.platform;
+
+  beforeEach(async () => {
+    vi.clearAllMocks();
+    mockDbInstance.__throwOnConstruct = false;
+    // Force darwin so macOS-specific logic is exercised
+    Object.defineProperty(process, "platform", { value: "darwin", writable: true });
+    // Re-import to pick up fresh mocks each run
+    const mod = await import("../../src/app/api/oauth/cursor/auto-import/route.js");
+    GET = mod.GET;
+  });
+
+  afterEach(() => {
+    Object.defineProperty(process, "platform", { value: originalPlatform, writable: true });
+  });
+
+  // ── macOS path probing ────────────────────────────────────────────────
+
+  it("returns not-found when no macOS cursor db paths are accessible", async () => {
+    vi.mocked(fsPromises.access).mockRejectedValue(new Error("ENOENT"));
+
+    const response = await GET();
+
+    expect(response.body.found).toBe(false);
+    expect(response.body.error).toContain("Cursor database not found in known macOS locations");
+  });
+
+  it("returns descriptive error if macOS db file exists but cannot be opened", async () => {
+    vi.mocked(fsPromises.access).mockResolvedValue();
+    mockDbInstance.__throwOnConstruct = true;
+
+    const response = await GET();
+
+    expect(response.body.found).toBe(false);
+    expect(response.body.error).toContain("could not open it");
+    expect(response.body.error).toContain("SQLITE_CANTOPEN");
+  });
+
+  // ── Token extraction ──────────────────────────────────────────────────
+
+  it("extracts tokens using exact keys", async () => {
+    vi.mocked(fsPromises.access).mockResolvedValue();
+    mockDbInstance.prepare.mockReturnValue({
+      all: vi.fn().mockReturnValue([
+        { key: "cursorAuth/accessToken", value: "test-token" },
+        { key: "storage.serviceMachineId", value: "test-machine-id" },
+      ]),
+    });
+
+    const response = await GET();
+
+    expect(response.body.found).toBe(true);
+    expect(response.body.accessToken).toBe("test-token");
+    expect(response.body.machineId).toBe("test-machine-id");
+    expect(mockDbInstance.close).toHaveBeenCalled();
+  });
+
+  it("unwraps JSON-encoded string values", async () => {
+    vi.mocked(fsPromises.access).mockResolvedValue();
+    mockDbInstance.prepare.mockReturnValue({
+      all: vi.fn().mockReturnValue([
+        { key: "cursorAuth/accessToken", value: '"json-token"' },
+        { key: "storage.serviceMachineId", value: '"json-machine-id"' },
+      ]),
+    });
+
+    const response = await GET();
+
+    expect(response.body.found).toBe(true);
+    expect(response.body.accessToken).toBe("json-token");
+    expect(response.body.machineId).toBe("json-machine-id");
+  });
+
+  // ── Fuzzy fallback (macOS only) ───────────────────────────────────────
+
+  it("falls back to fuzzy key matching on macOS when exact keys are missing", async () => {
+    vi.mocked(fsPromises.access).mockResolvedValue();
+    mockDbInstance.prepare.mockImplementation((query) => {
+      if (query.includes("IN (")) {
+        return { all: vi.fn().mockReturnValue([]) };
+      }
+      // Fuzzy LIKE query
+      return {
+        all: vi.fn().mockReturnValue([
+          { key: "cursorAuth/someOtherAccessTokenKey", value: "fallback-token" },
+          { key: "storage.someMachineId", value: "fallback-machine" },
+        ]),
+      };
+    });
+
+    const response = await GET();
+
+    expect(response.body.found).toBe(true);
+    expect(response.body.accessToken).toBe("fallback-token");
+    expect(response.body.machineId).toBe("fallback-machine");
+  });
+
+  it("returns login-prompt error when tokens are missing even after fallback", async () => {
+    vi.mocked(fsPromises.access).mockResolvedValue();
+    mockDbInstance.prepare.mockReturnValue({
+      all: vi.fn().mockReturnValue([]),
+    });
+
+    const response = await GET();
+
+    expect(response.body.found).toBe(false);
+    expect(response.body.error).toContain("Please login to Cursor IDE first");
+  });
+
+  // ── Backwards-compatible: linux/win32 keep original single-path logic ─
+
+  it("linux uses single hardcoded path and original error message", async () => {
+    Object.defineProperty(process, "platform", { value: "linux", writable: true });
+    vi.mocked(fsPromises.access).mockRejectedValue(new Error("ENOENT"));
+    mockDbInstance.__throwOnConstruct = true;
+
+    const response = await GET();
+
+    expect(response.body.found).toBe(false);
+    expect(response.body.error).toBe(
+      "Cursor database not found. Make sure Cursor IDE is installed and you are logged in."
+    );
+    // fs/promises.access should NOT have been called (linux skips probing)
+    expect(fsPromises.access).not.toHaveBeenCalled();
+  });
+
+  it("unsupported platform returns 400", async () => {
+    Object.defineProperty(process, "platform", { value: "freebsd", writable: true });
+
+    const response = await GET();
+
+    expect(response.status).toBe(400);
+    expect(response.body.error).toBe("Unsupported platform");
+  });
+});