diff --git a/hermes_cli/update_custody.py b/hermes_cli/update_custody.py
index aab25efdfa..975f83f84f 100644
--- a/hermes_cli/update_custody.py
+++ b/hermes_cli/update_custody.py
@@ -262,8 +262,14 @@ def run(argv: Sequence[str], *, inherit_lock: bool = False, **kwargs) -> subproc
         try:
             stdout, stderr = proc.communicate(input, timeout=timeout)
         except subprocess.TimeoutExpired as exc:
+            _kill_tree(proc)
             proc.kill()
-            exc.stdout, exc.stderr = proc.communicate()
+            try:
+                exc.stdout, exc.stderr = proc.communicate(timeout=_DRAIN_SECONDS)
+            except subprocess.TimeoutExpired:
+                # A descendant the tree kill missed still holds the pipes: leave them to the
+                # reader threads (closing a pipe a thread is reading blocks) and give up on them.
+                proc.stdin = proc.stdout = proc.stderr = None
             raise
         except BaseException:
             proc.kill()
@@ -274,6 +280,20 @@ def run(argv: Sequence[str], *, inherit_lock: bool = False, **kwargs) -> subproc
     return subprocess.CompletedProcess(proc.args, code, stdout, stderr)
 
 
+# How long a timed-out child's output may still drain after its tree was killed.
+_DRAIN_SECONDS = 5
+
+
+def _kill_tree(proc: subprocess.Popen) -> None:
+    """Windows: kill the child AND what it started (git.exe's git-remote-https inherits the
+    stdout/stderr pipes; killing git.exe alone leaves communicate() waiting on the helper). Not
+    TerminateJobObject: the job also holds the update's other children."""
+    with contextlib.suppress(OSError, subprocess.SubprocessError):
+        subprocess.run(["taskkill", "/T", "/F", "/PID", str(proc.pid)], stdin=subprocess.DEVNULL,
+                       stdout=subprocess.DEVNULL, stderr=subprocess.DEVNULL, timeout=10,
+                       creationflags=getattr(subprocess, "CREATE_NO_WINDOW", 0))
+
+
 def run_git(git_cmd: Sequence[str], args: Sequence[str], **kwargs) -> subprocess.CompletedProcess:
     """THE updater git runner: custody config in argv, the lock fd only into local mutators,
     Windows job binding inside an update. ``kwargs`` are ``subprocess.run``'s."""
diff --git a/tests/hermes_cli/test_update_custody.py b/tests/hermes_cli/test_update_custody.py
index 05da483d86..3a3bfaa9bb 100644
--- a/tests/hermes_cli/test_update_custody.py
+++ b/tests/hermes_cli/test_update_custody.py
@@ -300,3 +300,19 @@ def test_run_git_hands_the_lock_fd_to_local_mutators_only(repo, tmp_path, monkey
         lock.release()
     assert ran.returncode == 0, ran.stderr
     assert out.read_text(encoding="utf-8-sig").split() == (["yes"] if holds else ["no"]), args
+
+
+@pytest.mark.platforms("posix")
+def test_a_timed_out_child_never_waits_on_a_grandchild_holding_its_pipes(monkeypatch):
+    """N14: the in-update (Windows) run() killed only the direct child on a timeout, then waited
+    unbounded for the pipes a grandchild still held (git-remote-https under a stalled fetch).
+    Driven here through that branch with a POSIX grandchild the tree kill (taskkill) cannot reach."""
+    from hermes_cli import update_custody
+
+    monkeypatch.setattr(update_custody.sys, "platform", "win32")
+    monkeypatch.setattr(update_custody, "_held", lambda: {"fd": None})
+    monkeypatch.setattr(update_custody, "popen", lambda argv, **kw: subprocess.Popen(list(argv), **kw))
+    started = time.monotonic()
+    with pytest.raises(subprocess.TimeoutExpired):
+        update_custody.run(["sh", "-c", "sleep 20 & sleep 20"], capture_output=True, timeout=0.5)
+    assert time.monotonic() - started < 15, "run() waited on a grandchild after the timeout"