@yansigit/opencodex 2.31.0

package/src/lib/windows-secret-acl.ts

@@ -0,0 +1,854 @@
+/**
+ * Windows per-user NTFS ACL hardening for secret files and directories.
+ *
+ * On Windows, `chmod` only controls POSIX-style bits in the ACE list and does NOT remove
+ * inherited permissions from other users. Real per-user isolation requires icacls to:
+ *   1. Grant the current user full control (icacls path /grant:r "CURRENTUSER:(F)")
+ *   2. Disable inheritance               (icacls path /inheritance:r)
+ *   3. Strip broad explicit grants by SID (Everyone, Users, Authenticated Users)
+ *
+ * Owner grant MUST precede `/inheritance:r`. That flag is destructive: it drops inherited
+ * ACEs immediately. If a later step times out after inheritance is removed but before an
+ * explicit owner ACE exists, the temp is left with a protected empty DACL — owned by the
+ * current user yet unreadable/ununlinkable until Full Control is restored (issue #596).
+ *
+ * On non-Windows platforms the helpers fall through to the caller's existing chmod-based
+ * behaviour: they return ok:true without invoking any external process.
+ *
+ * Design:
+ *   hardenSecretPath(path, { required: false }) — non-fatal read-path mode.
+ *     Never throws. Returns { ok, diagnostics? }.
+ *   hardenSecretPath(path, { required: true })  — write-path mode.
+ *     Throws a sanitized error (no raw path) on every Windows ACL failure,
+ *     including genuine icacls timeouts. Required secret publication therefore
+ *     fails closed; only required:false read-path probes may soft-fail.
+ *   hardenSecretPathAsync / hardenSecretDirAsync — same policy, async icacls
+ *     runner so the event loop is not held for the child lifetime (#612).
+ *   HardenOptions.timeoutMemoKey — optional destination-path key for the
+ *     timeout memo (atomic writers mint unique temps; never a parent directory).
+ *   hardenSecretDir  — same contract for directories.
+ */
+
+import { existsSync, statSync } from "node:fs";
+import { env, platform } from "node:process";
+import { resolveTrustedWindowsIcaclsExe } from "./windows-elevation";
+import {
+  resolveCurrentWindowsPrincipal,
+  resolveCurrentWindowsPrincipalAsync,
+  setSyntheticWindowsPrincipalForTests,
+} from "./windows-user-principal";
+
+const hardenedDirectories = new Map<string, HardenedIdentity>();
+const hardenedPaths = new Map<string, HardenedIdentity>();
+/**
+ * Paths whose harden TIMED OUT this process: do not re-stall every loadConfig on them.
+ * `false` means one explicitly authorized recovery attempt remains; `true` means
+ * that attempt was consumed. Ordinary callers never consume it.
+ */
+const timedOutPaths = new Map<string, boolean>();
+
+/**
+ * The memo value: `object:freshness` for a file a harden was actually attributed
+ * to.
+ *
+ * There is deliberately no null member. An observation that cannot be read is
+ * not stored at all — the entry is deleted — because a "recorded as unverifiable"
+ * value was dead code the moment attribution became a before/after comparison,
+ * and a branch nothing can reach is a branch no test can defend.
+ */
+type HardenedIdentity = string;
+
+/**
+ * What a stat can tell us about WHICH OBJECT is at a path.
+ *
+ * Two fields, deliberately separated, because conflating them shipped a bug:
+ *
+ * - `object` — `dev:ino`. Answers "is this the same file". Survives an ACL or
+ *   permission change, which is exactly what we need across an icacls call.
+ * - `freshness` — `ctimeNs`. Answers "has this file's metadata moved since". It
+ *   distinguishes an unlink/recreate that ext4 gave the same inode back for, and
+ *   it MOVES when permissions change.
+ *
+ * The first version used `dev:ino:ctimeNs` for both jobs. Since chmod bumps ctime
+ * — probed, `{ctimeChangedByChmod: true}` — and icacls is a permission change, the
+ * before/after comparison would have rejected its own successful harden and failed
+ * closed on every first harden on Windows. Requiring the identity to be unchanged
+ * across an operation whose entire purpose is to change it is not a strict check;
+ * it is a broken one.
+ */
+interface PathObservation {
+  readonly object: string;
+  readonly freshness: string;
+}
+
+/**
+ * Observe which object is at a path, and how fresh it is.
+ *
+ * `dev:ino` alone is not enough to detect a replacement, which a Linux CI run
+ * proved: ext4 reuses the inode of an unlinked file immediately — 100 of 100
+ * unlink/recreate cycles produced the SAME `ino`, while macOS reused none in 200
+ * and happily reported the earlier fix working. That is why `freshness` exists;
+ * `ctimeNs` differed in 100 of 100 of those same cycles.
+ *
+ * `bigint: true` is used because `ctimeNs` exists only in that variant.
+ *
+ * Test seam: `setStatForTests` replaces this reader so a test can vary `dev`,
+ * `ino`, and `ctimeNs` independently. Mirroring the implementation's string
+ * format in test setup proves nothing about which components production uses —
+ * an audit removed `dev` and all forty tests still passed.
+ *
+ * UNVERIFIED: the plain `ino` is reported to be 0 on NTFS while the bigint form
+ * carries the file index, and the zero-ino guard exists for that case. Neither
+ * Darwin nor Linux CI can confirm it and no pinned-Bun Windows probe has run.
+ * It is defensive code, not a demonstrated platform fact.
+ */
+type StatReader = (path: string) => { dev: bigint; ino: bigint; ctimeNs: bigint };
+
+const defaultStatReader: StatReader = path => {
+  const s = statSync(path, { bigint: true });
+  return { dev: s.dev, ino: s.ino, ctimeNs: s.ctimeNs };
+};
+
+let statReader: StatReader = defaultStatReader;
+
+/** Test seam: drive dev / ino / ctime independently. */
+export function setStatForTests(reader: StatReader | null): void {
+  statReader = reader ?? defaultStatReader;
+}
+
+function observe(targetPath: string): PathObservation | null {
+  try {
+    const s = statReader(targetPath);
+    if (s.ino === 0n) return null;
+    return { object: `${s.dev}:${s.ino}`, freshness: `${s.ctimeNs}` };
+  } catch {
+    return null;
+  }
+}
+
+function memoValue(seen: PathObservation): HardenedIdentity {
+  return `${seen.object}:${seen.freshness}`;
+}
+
+/**
+ * True only when this exact FILE was hardened, not merely this pathname.
+ *
+ * The memo used to be a `Set<string>` of paths. A stable destination — such as
+ * the coordinator database `hardenStableLockFile` hardens — can be unlinked and
+ * recreated at the same name, and the replacement inherited the previous file's
+ * hardening while never having been through icacls. Ephemeral temps escaped this
+ * only because atomic writers call `forgetEphemeralSecretPath` once the temp is
+ * gone; nothing does that for a stable path.
+ */
+function memoSatisfied(cache: Map<string, HardenedIdentity>, targetPath: string): boolean {
+  const remembered = cache.get(targetPath);
+  if (remembered === undefined) return false;
+  const current = observe(targetPath);
+  // Unreadable now is not "unchanged": re-harden rather than trust a value we
+  // cannot confirm still describes what is there.
+  //
+  // A miss RETIRES the entry rather than leaving it. Keeping it left the cache in
+  // a state nothing could justify: after a mismatch and a failed re-harden, the
+  // stale value survived, so restoring the old identity would satisfy it again
+  // without any ACL work. That needs exact-identity ABA to bite — outside the
+  // proof bound this unit claims — but "the consequence is out of scope" is not a
+  // reason to keep an entry we have just proven does not describe what is there.
+  if (current === null || memoValue(current) !== remembered) {
+    cache.delete(targetPath);
+    return false;
+  }
+  return true;
+}
+
+/**
+ * Record a harden ONLY if the file we hardened is still the file at that path.
+ *
+ * Reading identity after the ACL sequence returns answers "what is there now",
+ * which is not the same question as "what did icacls operate on". A replacement
+ * landing mid-sequence — probed by swapping the file during the final
+ * `/remove:g` — made the memo remember the REPLACEMENT as hardened, so the next
+ * acquisition skipped ACL work on a file that had never seen it:
+ *
+ *   {identityChangedDuringHarden: true, callsForOriginal: 3, totalCalls: 3,
+ *    replacementWasHardened: false}
+ *
+ * So the OBJECT is captured before the sequence and compared after it. Only the
+ * object — `dev:ino` — because icacls changes permissions, and `ctimeNs` moves
+ * when permissions change (probed: `{ctimeChangedByChmod: true}`). Comparing the
+ * full identity across the call would have rejected every successful harden and
+ * failed closed on the first harden on Windows: the check would have been
+ * demanding that an operation not do the thing it exists to do.
+ *
+ * The memo then stores the object plus the freshness read AFTER hardening, which
+ * is the state a later lookup should match.
+ *
+ * A changed object, or an unreadable observation at either end, means we cannot
+ * say what was hardened: the memo is cleared rather than written, and required
+ * callers fail closed. An optional caller soft-fails, as it does for every other
+ * unproven ACL.
+ *
+ * Returns true when the harden may be reported successful.
+ */
+function recordHarden(
+  cache: Map<string, HardenedIdentity>,
+  targetPath: string,
+  before: PathObservation | null,
+): boolean {
+  const after = observe(targetPath);
+  if (before === null || after === null || before.object !== after.object) {
+    // Never leave a memo behind for a file we cannot vouch for, including one
+    // written by an earlier successful harden of a now-replaced file.
+    cache.delete(targetPath);
+    return false;
+  }
+  cache.set(targetPath, memoValue(after));
+  return true;
+}
+
+const SUBSTITUTED_DIAGNOSTIC =
+  "ACL hardening could not be attributed — the file at this path changed during hardening";
+
+export interface HardenResult {
+  ok: boolean;
+  diagnostics?: string;
+}
+
+export interface HardenOptions {
+  required: boolean;
+  /**
+   * Optional timeout-memo key distinct from `targetPath` (issue #612).
+   * Atomic writers mint a fresh `.tmp` path per write; keying the timeout cache by the
+   * final destination path prevents re-stalling the event loop on every subsequent temp.
+   * Must NOT be a parent directory — directory ACLs are not authoritative for new files.
+   */
+  timeoutMemoKey?: string;
+  /**
+   * Consume the one recovery attempt for a previously timed-out memo key.
+   * Only a caller that owns its own single-flight and bounded retry policy should
+   * set this. It never clears or bypasses an already-consumed timeout memo.
+   */
+  retryTimedOutOnce?: boolean;
+}
+
+/**
+ * Total icacls budget per harden call — ALL steps share it, including the single
+ * timeout retry and the diagnostic verification pass (no per-attempt fresh budget:
+ * loadConfig hardens dir+config+auth sequentially, so per-attempt budgets stack
+ * into multi-minute startup stalls). Override with OPENCODEX_ACL_TIMEOUT_MS
+ * (integer ms, clamped to [1000, 60000]; invalid values fall back to 30000).
+ *
+ * The default was 5s until #1156. One envelope has to cover the whole sequence —
+ * `/grant:r`, `/inheritance:r`, `/remove:g`, plus the conditional `/findsid`
+ * verification — and on machines where icacls is slow (Defender real-time scanning,
+ * roaming profiles, a domain-controller round trip) 5s ran out mid-sequence. The
+ * harden then failed closed, the native-main owner published a permanent
+ * `unavailable`, and every native request returned 503 until restart. A slow start
+ * is recoverable; that is not.
+ *
+ * The cost is honest and worth stating: because loadConfig hardens three paths
+ * sequentially, the timeout-path worst case at load is ~90s, and the owner path
+ * (initial call + one recovery) is ~60.25s. Both require icacls to be
+ * pathologically slow on every call; a healthy machine finishes in milliseconds
+ * and sees no change. Operators who prefer the old bound can set the env override.
+ */
+const HARDEN_DEADLINE_DEFAULT_MS = 30_000;
+const HARDEN_DEADLINE_MIN_MS = 1_000;
+const HARDEN_DEADLINE_MAX_MS = 60_000;
+
+/** Resolve the total harden budget once per call (env mutation cannot change it midway). */
+function resolveHardenDeadlineMs(): number {
+  const raw = env["OPENCODEX_ACL_TIMEOUT_MS"]?.trim();
+  if (!raw) return HARDEN_DEADLINE_DEFAULT_MS;
+  const parsed = Number(raw);
+  if (!Number.isSafeInteger(parsed)) return HARDEN_DEADLINE_DEFAULT_MS;
+  return Math.min(HARDEN_DEADLINE_MAX_MS, Math.max(HARDEN_DEADLINE_MIN_MS, parsed));
+}
+
+export interface IcaclsResult {
+  success: boolean;
+  exitCode: number | null;
+  timedOut: boolean;
+  stdout: string;
+}
+
+type IcaclsRunner = (args: string[], timeoutMs: number) => IcaclsResult;
+type AsyncIcaclsRunner = (args: string[], timeoutMs: number) => Promise<IcaclsResult>;
+
+function resolveIcaclsExecutable(): string {
+  // Same authority as schtasks/powershell: never take icacls from PATH.
+  // A bun-shim or stripped PATH makes `icacls.exe` throw ENOENT, which used to
+  // surface as "filesystem may not support per-user NTFS ACLs".
+  return resolveTrustedWindowsIcaclsExe();
+}
+
+function spawnFailedResult(): IcaclsResult {
+  return { success: false, exitCode: null, timedOut: false, stdout: "" };
+}
+
+/**
+ * Spawn icacls asynchronously, or return null when the executable cannot be
+ * launched. The pipe/ignore stdio literals stay inferred here so `stdout` keeps
+ * its `ReadableStream` type instead of widening to the generic default.
+ */
+function trySpawnIcacls(args: string[]) {
+  try {
+    return Bun.spawn([resolveIcaclsExecutable(), ...args], {
+      stdin: "ignore",
+      stdout: "pipe",
+      stderr: "ignore",
+      windowsHide: true,
+    });
+  } catch {
+    return null;
+  }
+}
+
+function defaultIcaclsRunner(args: string[], timeoutMs: number): IcaclsResult {
+  // Bun.spawnSync with windowsHide: Node execFileSync has hung under the GUI/proxy even
+  // with windowsHide, and console-subsystem tools flash a visible window otherwise.
+  try {
+    const result = Bun.spawnSync([resolveIcaclsExecutable(), ...args], {
+      stdin: "ignore",
+      stdout: "pipe",
+      stderr: "ignore",
+      timeout: timeoutMs,
+      windowsHide: true,
+    });
+    return {
+      success: result.success,
+      exitCode: result.exitCode,
+      timedOut: result.exitedDueToTimeout ?? false,
+      stdout: result.stdout ? result.stdout.toString() : "",
+    };
+  } catch {
+    return spawnFailedResult();
+  }
+}
+
+/**
+ * Async icacls runner (#612): yields the event loop while waiting for the child.
+ * Timeout provenance is recorded by our timer (async Subprocess has no exitedDueToTimeout);
+ * we still await process exit before classifying so settlement is confirmed.
+ */
+async function defaultAsyncIcaclsRunner(args: string[], timeoutMs: number): Promise<IcaclsResult> {
+  const proc = trySpawnIcacls(args);
+  if (!proc) return spawnFailedResult();
+  let timedOutByUs = false;
+  const timer = setTimeout(() => {
+    timedOutByUs = true;
+    try { proc.kill(); } catch { /* already exited */ }
+  }, Math.max(1, timeoutMs));
+  let exitCode: number | null = null;
+  try {
+    exitCode = await proc.exited;
+  } finally {
+    clearTimeout(timer);
+  }
+  const stdout = proc.stdout
+    ? await new Response(proc.stdout).text().catch(() => "")
+    : "";
+  const timedOut = timedOutByUs;
+  return {
+    success: !timedOut && exitCode === 0,
+    exitCode: timedOut ? null : exitCode,
+    timedOut,
+    stdout,
+  };
+}
+
+let icaclsRunner: IcaclsRunner = defaultIcaclsRunner;
+let asyncIcaclsRunner: AsyncIcaclsRunner = defaultAsyncIcaclsRunner;
+let platformOverride: string | null = null;
+let nowFn: () => number = Date.now;
+
+/** Test seam: replace the icacls process runner. Pass null to restore the default. */
+export function setIcaclsRunnerForTests(runner: IcaclsRunner | null): void {
+  icaclsRunner = runner ?? defaultIcaclsRunner;
+}
+
+/** Test seam: replace the async icacls runner. Pass null to restore the default. */
+export function setAsyncIcaclsRunnerForTests(runner: AsyncIcaclsRunner | null): void {
+  asyncIcaclsRunner = runner ?? defaultAsyncIcaclsRunner;
+}
+
+/**
+ * Test seam: force the platform gate (e.g. "win32") so CI on POSIX reaches the runner.
+ *
+ * Faking win32 on a host without System32 also has to supply a principal, or
+ * every forced-branch test would fail on the identity lookup instead of
+ * exercising icacls. The synthetic value is registered with the resolver, not
+ * chosen here, so a test that injects its own runner still wins.
+ */
+const SYNTHETIC_TEST_PRINCIPAL = "*S-1-5-21-1-2-3-1001";
+
+export function setPlatformForTests(value: string | null): void {
+  platformOverride = value;
+  setSyntheticWindowsPrincipalForTests(
+    value === "win32" && platform !== "win32" ? SYNTHETIC_TEST_PRINCIPAL : null,
+  );
+}
+
+/** Test seam: injectable clock for deadline tests (no real sleeps). */
+export function setNowForTests(fn: (() => number) | null): void {
+  nowFn = fn ?? Date.now;
+}
+
+/** Test seam: clear memo/failure caches between cases. */
+export function resetHardenedStateForTests(): void {
+  hardenedDirectories.clear();
+  hardenedPaths.clear();
+  timedOutPaths.clear();
+}
+
+/** Forget a successful harden only after this exact ephemeral path is gone. */
+export function forgetHardenedSecretPath(targetPath: string): void {
+  hardenedPaths.delete(targetPath);
+}
+
+/**
+ * Ephemeral-path lifecycle release: clears the success memo AND any timeout
+ * memo keyed by THIS TEMP path in both namespaces. Call only after the temp is
+ * proven absent (successful rename, successful unlink, ENOENT, or an explicit
+ * non-existence check). Never pass a stable destination: destination-keyed
+ * timeout memos are intentional anti-restall state and are not touched here.
+ */
+export function forgetEphemeralSecretPath(tempPath: string): void {
+  hardenedPaths.delete(tempPath);
+  timedOutPaths.delete(`required:${tempPath}`);
+  timedOutPaths.delete(`optional:${tempPath}`);
+}
+
+/** Directory counterpart for a proven-absent ephemeral staging root. */
+export function forgetEphemeralSecretDir(tempPath: string): void {
+  hardenedDirectories.delete(tempPath);
+  timedOutPaths.delete(`required:${tempPath}`);
+  timedOutPaths.delete(`optional:${tempPath}`);
+}
+
+/** Test seam: timeout memo sets return to baseline after ephemeral cleanup. */
+export function timedOutSecretPathCountForTests(): number {
+  return timedOutPaths.size;
+}
+
+/** Test seam for proving ephemeral success memos do not grow across replacements. */
+export function hardenedSecretPathCountForTests(): number {
+  return hardenedPaths.size;
+}
+
+/**
+ * Directory counterpart. It had no seam, and that absence hid a real gap: a
+ * directory-only pathname memo passed every file-based test in this suite.
+ */
+export function hardenedSecretDirCountForTests(): number {
+  return hardenedDirectories.size;
+}
+
+function effectivePlatform(): string {
+  return platformOverride ?? platform;
+}
+
+/** Test-aware platform predicate for callers that must avoid even a no-op ACL call. */
+export function windowsSecretAclApplies(): boolean {
+  return (platformOverride ?? process.platform) === "win32";
+}
+
+/** Error carrying an honest code: ETIMEDOUT only for real timeouts, EICACLS otherwise. */
+function icaclsError(step: string, result: IcaclsResult): NodeJS.ErrnoException {
+  const err = new Error(
+    result.timedOut ? `icacls ${step} timed out` : `icacls ${step} exited ${result.exitCode ?? "null"}`,
+  ) as NodeJS.ErrnoException;
+  err.code = result.timedOut ? "ETIMEDOUT" : "EICACLS";
+  return err;
+}
+
+/**
+ * The ACL principal is the effective token SID and nothing else.
+ *
+ * There is no name-shaped fallback here, and that absence is the fix for #1149
+ * rather than an omission. `USERDOMAIN\USERNAME` has the right shape but is not
+ * evidence of the current token's subject, and both variables are writable by
+ * the process that launched us. Granting Full Control to a wrong principal and
+ * then running `/inheritance:r` is destructive in both directions: another
+ * account can be left holding the secret, or the file can be left with no ACE
+ * the current user can use. When the SID cannot be resolved we decline.
+ *
+ * Non-Windows hosts that force this branch through `setPlatformForTests` get
+ * their principal from `setSyntheticWindowsPrincipalForTests`, which lives with
+ * the resolver so an injected runner can still take precedence over it.
+ */
+function currentWindowsPrincipal(deadline: number): string {
+  return resolveCurrentWindowsPrincipal(deadline - nowFn());
+}
+
+async function currentWindowsPrincipalAsync(deadline: number): Promise<string> {
+  return resolveCurrentWindowsPrincipalAsync(deadline - nowFn());
+}
+
+/**
+ * Run icacls to harden a single file system entry.
+ * Order is intentional (issue #596): grant the owner ACE first so a later
+ * `/inheritance:r` or `/remove:g` timeout cannot strand a protected zero-ACE DACL.
+ *
+ * We do NOT use a shell string; all arguments are passed as an array so no
+ * shell injection is possible even for paths with unusual characters.
+ *
+ * Throws the raw child_process error on failure (caller sanitizes).
+ */
+const BROAD_SIDS = ["*S-1-1-0", "*S-1-5-11", "*S-1-5-32-545"] as const;
+
+function grantAce(user: string, directory: boolean): string {
+  return directory ? `${user}:(OI)(CI)(F)` : `${user}:(F)`;
+}
+
+function runIcacls(targetPath: string, directory: boolean, deadline: number): void {
+  const principal = currentWindowsPrincipal(deadline);
+
+  // The deadline is owned by hardenEntry (total budget incl. retry + verification).
+  const run = (step: string, args: string[]): IcaclsResult => {
+    const remaining = deadline - nowFn();
+    if (remaining <= 0) {
+      throw icaclsError(step, { success: false, exitCode: null, timedOut: true, stdout: "" });
+    }
+    return icaclsRunner(args, remaining);
+  };
+  const runOrThrow = (step: string, args: string[]): void => {
+    const result = run(step, args);
+    if (!result.success) throw icaclsError(step, result);
+  };
+
+  // Step 1: grant current user full control BEFORE any destructive ACL change.
+  // If this fails, inheritance is untouched and the writer keeps inherited access.
+  runOrThrow("/grant:r", [targetPath, "/grant:r", grantAce(principal, directory)]);
+
+  // Step 2: disable inheritance and remove inherited ACEs. The explicit owner ACE
+  // from step 1 survives this transition, so a later failure still leaves cleanup access.
+  runOrThrow("/inheritance:r", [targetPath, "/inheritance:r"]);
+
+  // Step 3: remove broad explicit grants using stable SIDs (not localized names).
+  // Missing ACEs can yield a non-zero exit; verify with locale-independent /findsid
+  // before accepting the failure as harmless — a swallowed real failure would leave
+  // Everyone/Users/Authenticated Users grants while reporting hardened.
+  // `/remove:g` cannot remove the explicit current-user ACE installed in step 1.
+  const removal = run("/remove:g", [targetPath, "/remove:g", ...BROAD_SIDS]);
+  if (!removal.success) {
+    if (removal.timedOut) throw icaclsError("/remove:g", removal);
+    for (const sid of BROAD_SIDS) {
+      const found = run("/findsid", [targetPath, "/findsid", sid]);
+      if (!found.success) throw icaclsError("/findsid", found);
+      // icacls /findsid echoes the target path in its "SID Found" line only when the SID
+      // still holds an ACE; the summary lines carry only counts. Matching the path echo —
+      // not the (localized) prose — keeps the check locale-independent.
+      if (found.stdout.includes(targetPath)) {
+        throw icaclsError("/remove:g", removal);
+      }
+    }
+  }
+}
+
+/** Async counterpart of runIcacls — same step order and timeout/error classification (#612). */
+async function runIcaclsAsync(targetPath: string, directory: boolean, deadline: number): Promise<void> {
+  const principal = await currentWindowsPrincipalAsync(deadline);
+
+  const run = async (step: string, args: string[]): Promise<IcaclsResult> => {
+    const remaining = deadline - nowFn();
+    if (remaining <= 0) {
+      throw icaclsError(step, { success: false, exitCode: null, timedOut: true, stdout: "" });
+    }
+    return asyncIcaclsRunner(args, remaining);
+  };
+  const runOrThrow = async (step: string, args: string[]): Promise<void> => {
+    const result = await run(step, args);
+    if (!result.success) throw icaclsError(step, result);
+  };
+
+  await runOrThrow("/grant:r", [targetPath, "/grant:r", grantAce(principal, directory)]);
+  await runOrThrow("/inheritance:r", [targetPath, "/inheritance:r"]);
+
+  const removal = await run("/remove:g", [targetPath, "/remove:g", ...BROAD_SIDS]);
+  if (!removal.success) {
+    if (removal.timedOut) throw icaclsError("/remove:g", removal);
+    for (const sid of BROAD_SIDS) {
+      const found = await run("/findsid", [targetPath, "/findsid", sid]);
+      if (!found.success) throw icaclsError("/findsid", found);
+      if (found.stdout.includes(targetPath)) {
+        throw icaclsError("/remove:g", removal);
+      }
+    }
+  }
+}
+
+/**
+ * Sanitize an error from a failed ACL operation into a safe diagnostic string.
+ * The raw path must not appear in the returned string (it may contain
+ * sensitive username components or PII from the home directory path).
+ */
+function sanitizeDiagnostics(error: unknown): string {
+  // We do not expose the raw error message or any path-like fragments —
+  // just an honest, code-specific cause (issue #160: a transient icacls stall
+  // must not read like filesystem non-support).
+  const code = error instanceof Error && "code" in error ? String((error as NodeJS.ErrnoException).code) : "";
+  switch (code) {
+    case "ETIMEDOUT":
+      return "ACL hardening timed out (ETIMEDOUT) — transient icacls stall; the volume may still support per-user NTFS ACLs";
+    case "EPERM":
+    case "EACCES":
+      return `ACL hardening failed (${code}) — permission denied running icacls`;
+    case "EICACLS":
+      return "ACL hardening failed (EICACLS) — icacls command error; filesystem may not support per-user NTFS ACLs";
+    case "EACLIDENTITY":
+      return "ACL hardening failed (EACLIDENTITY) — the effective Windows account SID could not be resolved";
+    default:
+      return `ACL hardening failed${code ? ` (${code})` : ""} — filesystem may not support per-user NTFS ACLs`;
+  }
+}
+
+function isTimeoutError(error: unknown): boolean {
+  return error instanceof Error && "code" in error
+    && String((error as NodeJS.ErrnoException).code) === "ETIMEDOUT";
+}
+
+/** Preserve only the bounded machine-readable cause on a sanitized public error. */
+function sanitizedAclError(diagnostics: string, cause: unknown): NodeJS.ErrnoException {
+  const error = new Error(diagnostics) as NodeJS.ErrnoException;
+  const code = cause && typeof cause === "object" && "code" in cause
+    ? String((cause as { code?: unknown }).code)
+    : "";
+  // EACLIDENTITY belongs here for the same reason as the rest: a caller that
+  // catches a required-mode failure has to tell "the SID could not be resolved"
+  // apart from "icacls stalled". Without it the code was dropped and only the
+  // message carried the cause, which no caller can branch on.
+  if (
+    code === "ETIMEDOUT" ||
+    code === "EICACLS" ||
+    code === "EACCES" ||
+    code === "EPERM" ||
+    code === "EACLIDENTITY"
+  ) {
+    error.code = code;
+  }
+  return error;
+}
+
+function previousTimeoutError(retryConsumed: boolean): NodeJS.ErrnoException {
+  if (retryConsumed) {
+    const error = new Error(
+      "ACL hardening skipped — the previous timeout recovery was already consumed",
+    ) as NodeJS.ErrnoException;
+    error.code = "EACLRETRYEXHAUSTED";
+    return error;
+  }
+  return sanitizedAclError(
+    "ACL hardening skipped — previous attempt timed out",
+    Object.assign(new Error("timeout"), { code: "ETIMEDOUT" }),
+  );
+}
+
+/** Consume, but never reset, the single explicit recovery attempt for this key. */
+function timeoutMemoErrorIfBlocked(
+  memoKey: string,
+  opts: HardenOptions,
+): NodeJS.ErrnoException | null {
+  const retryConsumed = timedOutPaths.get(memoKey);
+  if (retryConsumed === undefined) return null;
+  if (opts.retryTimedOutOnce && retryConsumed === false) {
+    timedOutPaths.set(memoKey, true);
+    return null;
+  }
+  return previousTimeoutError(retryConsumed);
+}
+
+function recordTimeout(memoKey: string): void {
+  if (!timedOutPaths.has(memoKey)) timedOutPaths.set(memoKey, false);
+}
+
+/**
+ * Diagnostic-only post-timeout probe (never promotes to ok:true — a clean /findsid
+ * does not prove inheritance was disabled or the user grant ran; only a fully
+ * completed harden sequence may enter the hardened cache). Bounded by the remaining
+ * total budget; returns a short state note for the soft-fail diagnostic.
+ */
+function describeAclStateAfterTimeout(targetPath: string, deadline: number): string {
+  try {
+    for (const sid of BROAD_SIDS) {
+      const remaining = deadline - nowFn();
+      if (remaining <= 0) return "ACL state unverified (budget exhausted)";
+      const found = icaclsRunner([targetPath, "/findsid", sid], remaining);
+      if (!found.success) return "ACL state unverified (probe failed)";
+      if (found.stdout.includes(targetPath)) return "broad ACL grants still present";
+    }
+    return "no broad ACL grants detected (hardening still incomplete)";
+  } catch {
+    return "ACL state unverified (probe failed)";
+  }
+}
+
+async function describeAclStateAfterTimeoutAsync(targetPath: string, deadline: number): Promise<string> {
+  try {
+    for (const sid of BROAD_SIDS) {
+      const remaining = deadline - nowFn();
+      if (remaining <= 0) return "ACL state unverified (budget exhausted)";
+      const found = await asyncIcaclsRunner([targetPath, "/findsid", sid], remaining);
+      if (!found.success) return "ACL state unverified (probe failed)";
+      if (found.stdout.includes(targetPath)) return "broad ACL grants still present";
+    }
+    return "no broad ACL grants detected (hardening still incomplete)";
+  } catch {
+    return "ACL state unverified (probe failed)";
+  }
+}
+
+function timeoutMemoKey(targetPath: string, opts: HardenOptions): string {
+  // Destination-path memo only (issue #612). Never a parent directory — directory ACLs
+  // are not authoritative for newly created temps.
+  //
+  // Namespace by required-ness (#766): a soft `required:false` timeout during loadConfig
+  // must not poison a later `required:true` management-token harden of the same path.
+  const base = opts.timeoutMemoKey ?? targetPath;
+  return `${opts.required ? "required" : "optional"}:${base}`;
+}
+
+/**
+ * Shared harden flow for files and directories: one total budget (env-configurable)
+ * covering the initial attempt, ONE timeout retry, and the diagnostic verification.
+ * Required paths fail closed for every hardening failure, including genuine
+ * timeouts. Optional read paths soft-fail with an honest diagnostic.
+ */
+function hardenEntry(
+  targetPath: string,
+  directory: boolean,
+  opts: HardenOptions,
+  cache: Map<string, HardenedIdentity>,
+): HardenResult {
+  // Observed absence retires the memo. Leaving it would let a later file at this
+  // path satisfy the cache if the filesystem ever hands back a matching identity.
+  if (!existsSync(targetPath)) { cache.delete(targetPath); return { ok: true }; }
+  if (effectivePlatform() !== "win32") return { ok: true };
+  if (memoSatisfied(cache, targetPath)) return { ok: true };
+  const memoKey = timeoutMemoKey(targetPath, opts);
+  const timeoutMemoError = timeoutMemoErrorIfBlocked(memoKey, opts);
+  if (timeoutMemoError) {
+    if (opts.required) throw timeoutMemoError;
+    return { ok: false, diagnostics: timeoutMemoError.message };
+  }
+
+  const deadline = nowFn() + resolveHardenDeadlineMs();
+  let lastErr: unknown;
+  for (let attempt = 0; attempt < 2; attempt++) {
+    if (attempt > 0 && deadline - nowFn() <= 0) break; // retry only while budget remains
+    try {
+      // Captured BEFORE the sequence: this is the file we are about to harden.
+      const before = observe(targetPath);
+      runIcacls(targetPath, directory, deadline);
+      if (!recordHarden(cache, targetPath, before)) {
+        if (opts.required) throw new Error(SUBSTITUTED_DIAGNOSTIC);
+        return { ok: false, diagnostics: SUBSTITUTED_DIAGNOSTIC };
+      }
+      timedOutPaths.delete(memoKey);
+      return { ok: true };
+    } catch (err) {
+      // A substitution is not a transient icacls stall; do not spend the retry on it.
+      if (err instanceof Error && err.message === SUBSTITUTED_DIAGNOSTIC) throw err;
+      lastErr = err;
+      if (!isTimeoutError(err)) break; // real failures do not retry
+    }
+  }
+
+  const diagnostics = sanitizeDiagnostics(lastErr);
+  if (isTimeoutError(lastErr)) {
+    recordTimeout(memoKey);
+    const state = describeAclStateAfterTimeout(targetPath, deadline);
+    const annotated = `${diagnostics}; ${state}`;
+    if (opts.required) throw sanitizedAclError(annotated, lastErr);
+    console.warn(`[opencodex] ${annotated} — continuing without NTFS ACL harden`);
+    return { ok: false, diagnostics: annotated };
+  }
+  if (opts.required) throw sanitizedAclError(diagnostics, lastErr);
+  return { ok: false, diagnostics };
+}
+
+/** Async counterpart of hardenEntry — yields while waiting on icacls (#612). */
+async function hardenEntryAsync(
+  targetPath: string,
+  directory: boolean,
+  opts: HardenOptions,
+  cache: Map<string, HardenedIdentity>,
+): Promise<HardenResult> {
+  if (!existsSync(targetPath)) { cache.delete(targetPath); return { ok: true }; }
+  if (effectivePlatform() !== "win32") return { ok: true };
+  if (memoSatisfied(cache, targetPath)) return { ok: true };
+  const memoKey = timeoutMemoKey(targetPath, opts);
+  const timeoutMemoError = timeoutMemoErrorIfBlocked(memoKey, opts);
+  if (timeoutMemoError) {
+    if (opts.required) throw timeoutMemoError;
+    return { ok: false, diagnostics: timeoutMemoError.message };
+  }
+
+  const deadline = nowFn() + resolveHardenDeadlineMs();
+  let lastErr: unknown;
+  for (let attempt = 0; attempt < 2; attempt++) {
+    if (attempt > 0 && deadline - nowFn() <= 0) break;
+    try {
+      const before = observe(targetPath);
+      await runIcaclsAsync(targetPath, directory, deadline);
+      if (!recordHarden(cache, targetPath, before)) {
+        if (opts.required) throw new Error(SUBSTITUTED_DIAGNOSTIC);
+        return { ok: false, diagnostics: SUBSTITUTED_DIAGNOSTIC };
+      }
+      timedOutPaths.delete(memoKey);
+      return { ok: true };
+    } catch (err) {
+      if (err instanceof Error && err.message === SUBSTITUTED_DIAGNOSTIC) throw err;
+      lastErr = err;
+      if (!isTimeoutError(err)) break;
+    }
+  }
+
+  const diagnostics = sanitizeDiagnostics(lastErr);
+  if (isTimeoutError(lastErr)) {
+    recordTimeout(memoKey);
+    const state = await describeAclStateAfterTimeoutAsync(targetPath, deadline);
+    const annotated = `${diagnostics}; ${state}`;
+    if (opts.required) throw sanitizedAclError(annotated, lastErr);
+    console.warn(`[opencodex] ${annotated} — continuing without NTFS ACL harden`);
+    return { ok: false, diagnostics: annotated };
+  }
+  if (opts.required) throw sanitizedAclError(diagnostics, lastErr);
+  return { ok: false, diagnostics };
+}
+
+/**
+ * Harden a single file path with per-user NTFS ACLs on Windows.
+ * On non-Windows platforms, returns ok:true immediately (caller owns chmod).
+ *
+ * @param targetPath  Absolute path to the file to harden.
+ * @param opts        { required: boolean } — required:true throws on failure.
+ */
+export function hardenSecretPath(targetPath: string, opts: HardenOptions): HardenResult {
+  return hardenEntry(targetPath, false, opts, hardenedPaths);
+}
+
+/**
+ * Async harden for write paths that must not block the event loop (#612).
+ * Same success/timeout/error policy as hardenSecretPath.
+ */
+export function hardenSecretPathAsync(targetPath: string, opts: HardenOptions): Promise<HardenResult> {
+  return hardenEntryAsync(targetPath, false, opts, hardenedPaths);
+}
+
+/**
+ * Harden a directory path with per-user NTFS ACLs on Windows.
+ * On non-Windows platforms, returns ok:true immediately (caller owns chmod).
+ *
+ * @param targetPath  Absolute path to the directory to harden.
+ * @param opts        { required: boolean } — required:true throws on failure.
+ */
+export function hardenSecretDir(targetPath: string, opts: HardenOptions): HardenResult {
+  return hardenEntry(targetPath, true, opts, hardenedDirectories);
+}
+
+/**
+ * Async directory harden (#612). Same policy as hardenSecretDir.
+ */
+export function hardenSecretDirAsync(targetPath: string, opts: HardenOptions): Promise<HardenResult> {
+  return hardenEntryAsync(targetPath, true, opts, hardenedDirectories);
+}