fix(doctor): resolve macOS cloud paths through existing ancestors (#124299)

Co-authored-by: Peter Steinberger <steipete@gmail.com>

src/commands/doctor-state-integrity.cloud-storage.test.ts

@@ -1,9 +1,17 @@
 // Doctor state integrity cloud-storage tests cover macOS cloud-synced state directory detection.
+import fs from "node:fs";
 import os from "node:os";
 import path from "node:path";
-import { describe, expect, it, vi } from "vitest";
+import { afterEach, describe, expect, it, vi } from "vitest";
+import { createTempDirTracker } from "../../test/helpers/temp-dir.js";
 import { detectMacCloudSyncedStateDir } from "./doctor-state-integrity.js";
 
+const tempDirs = createTempDirTracker();
+
+afterEach(() => {
+  tempDirs.cleanup();
+});
+
 describe("detectMacCloudSyncedStateDir", () => {
   const home = "/Users/tester";
 
@@ -85,6 +93,53 @@ describe("detectMacCloudSyncedStateDir", () => {
     expect(result).toBeNull();
   });
 
+  it("follows a real symlink out of the sync root when the state dir leaf is absent", () => {
+    const sandbox = fs.realpathSync(tempDirs.make("openclaw-cloud-storage-symlink-"));
+    const realHome = path.join(sandbox, "home");
+    const cloudStorage = path.join(realHome, "Library", "CloudStorage");
+    const localTarget = path.join(sandbox, "local-openclaw");
+    fs.mkdirSync(cloudStorage, { recursive: true });
+    fs.mkdirSync(localTarget, { recursive: true });
+    const syncedLink = path.join(cloudStorage, "OneDrive-Personal");
+    fs.symlinkSync(localTarget, syncedLink, process.platform === "win32" ? "junction" : "dir");
+
+    const stateDir = path.join(syncedLink, "OpenClaw", ".openclaw");
+    expect(fs.existsSync(stateDir)).toBe(false);
+
+    expect(
+      detectMacCloudSyncedStateDir(stateDir, {
+        platform: "darwin",
+        homedir: realHome,
+      }),
+    ).toBeNull();
+  });
+
+  it("still warns for a real absent leaf that stays inside the sync root", () => {
+    const sandbox = fs.realpathSync(tempDirs.make("openclaw-cloud-storage-real-"));
+    const realHome = path.join(sandbox, "home");
+    const syncedDir = path.join(
+      realHome,
+      "Library",
+      "CloudStorage",
+      "OneDrive-Personal",
+      "OpenClaw",
+    );
+    fs.mkdirSync(syncedDir, { recursive: true });
+
+    const stateDir = path.join(syncedDir, ".openclaw");
+    expect(fs.existsSync(stateDir)).toBe(false);
+
+    expect(
+      detectMacCloudSyncedStateDir(stateDir, {
+        platform: "darwin",
+        homedir: realHome,
+      }),
+    ).toEqual({
+      path: path.resolve(stateDir),
+      storage: "CloudStorage provider",
+    });
+  });
+
   it("anchors cloud detection to OS homedir when OPENCLAW_HOME is overridden", () => {
     const stateDir = path.join(home, "Library", "CloudStorage", "iCloud Drive", ".openclaw");
     const originalOpenClawHome = process.env.OPENCLAW_HOME;

src/commands/doctor-state-integrity.ts

@@ -697,16 +697,14 @@ export function detectMacCloudSyncedStateDir(
       root: path.join(homedir, "Library", "CloudStorage"),
     },
   ];
-  const realPath = (deps?.resolveRealPath ?? tryResolveRealPath)(stateDir);
-  // Prefer the resolved target path when available so symlink prefixes do not
-  // misclassify local state dirs as cloud-synced.
-  const candidates = realPath ? [path.resolve(realPath)] : [path.resolve(stateDir)];
+  const resolveRealPath = deps?.resolveRealPath ?? tryResolveRealPath;
+  // Missing state leaves must still follow existing symlink ancestors, like the Linux detectors.
+  const resolvedStatePath =
+    resolvePathThroughExistingAncestor(stateDir, resolveRealPath, path) ?? path.resolve(stateDir);
 
-  for (const candidate of candidates) {
-    for (const { storage, root } of roots) {
-      if (isPathUnderRoot(candidate, root)) {
-        return { path: candidate, storage };
-      }
+  for (const { storage, root } of roots) {
+    if (isPathUnderRoot(resolvedStatePath, root)) {
+      return { path: resolvedStatePath, storage };
     }
   }