diff --git a/tests/test_cleanup.py b/tests/test_cleanup.py
new file mode 100644
index 0000000..6c02c26
--- /dev/null
+++ b/tests/test_cleanup.py
@@ -0,0 +1,597 @@
+"""
+Tests for rate-limit artifact cleanup in queue_manager.py.
+
+Covers _cleanup_rate_limit_artifacts() and _do_cleanup_rate_limit_artifacts().
+Uses tmp_path-based fake ~/.claude/ directories to avoid touching real state.
+"""
+
+import os
+import time
+from datetime import datetime, timedelta
+from pathlib import Path
+from unittest.mock import patch
+
+import pytest
+
+from claude_code_queue.models import (
+    ExecutionResult,
+    PromptStatus,
+    QueuedPrompt,
+    QueueState,
+    RateLimitInfo,
+)
+
+
+# ---------------------------------------------------------------------------
+# Helpers
+# ---------------------------------------------------------------------------
+
+SESSION_UUID = "00134021-1e30-4928-b9af-e92a676ab248"
+OTHER_UUID = "aaaaaaaa-bbbb-cccc-dddd-eeeeeeeeeeee"
+FAKE_WORKING_DIR = "/home/testuser/project"
+
+
+def _make_claude_dirs(tmp_path, working_dir=FAKE_WORKING_DIR):
+    """Create the four artifact directories under a fake ~/.claude/.
+
+    Returns (claude_dir, jsonl_dir, todos_dir, debug_dir, telemetry_dir).
+    """
+    claude_dir = tmp_path / ".claude"
+    encoded = working_dir.replace("/", "-")
+    jsonl_dir = claude_dir / "projects" / encoded
+    todos_dir = claude_dir / "todos"
+    debug_dir = claude_dir / "debug"
+    telemetry_dir = claude_dir / "telemetry"
+    for d in (jsonl_dir, todos_dir, debug_dir, telemetry_dir):
+        d.mkdir(parents=True)
+    return claude_dir, jsonl_dir, todos_dir, debug_dir, telemetry_dir
+
+
+def _write_file(path, size_bytes=100, content=None):
+    """Write a file with a given size or explicit content."""
+    if content is not None:
+        path.write_text(content)
+    else:
+        path.write_bytes(b"x" * size_bytes)
+
+
+def _make_prompt(working_dir=FAKE_WORKING_DIR):
+    """Create a prompt with last_executed set to 1 second ago and resolved working dir.
+
+    Using a 1-second offset avoids filesystem mtime-precision races: ext4 has
+    1-second granularity, so a file written "now" may have an mtime equal to
+    or slightly before datetime.now().timestamp().
+    """
+    p = QueuedPrompt(
+        id="abc12345",
+        content="test task",
+        working_directory=working_dir,
+        status=PromptStatus.EXECUTING,
+    )
+    p.last_executed = datetime.now() - timedelta(seconds=1)
+    p._resolved_working_directory = str(Path(working_dir).resolve())
+    return p
+
+
+def _rate_limit_result() -> ExecutionResult:
+    return ExecutionResult(
+        success=False,
+        output="usage limit reached",
+        error="",
+        rate_limit_info=RateLimitInfo(is_rate_limited=True, reset_time=None),
+        execution_time=0.1,
+    )
+
+
+# ===========================================================================
+# Basic Cleanup — All Four Artifact Types  (CLN-001 through CLN-004)
+# ===========================================================================
+
+
+def test_cleanup_deletes_rate_limited_jsonl(tmp_path, manager):  # CLN-001
+    """A small, recent JSONL file is deleted; its UUID is used for correlated cleanup."""
+    claude_dir, jsonl_dir, *_ = _make_claude_dirs(tmp_path)
+    prompt = _make_prompt()
+
+    jsonl_file = jsonl_dir / f"{SESSION_UUID}.jsonl"
+    _write_file(jsonl_file, size_bytes=4000)  # 4 KB — rate-limited size
+
+    with patch("pathlib.Path.home", return_value=tmp_path):
+        manager.state = QueueState()
+        manager.state.add_prompt(prompt)
+        manager._cleanup_rate_limit_artifacts(prompt)
+
+    assert not jsonl_file.exists(), "Rate-limited JSONL file should be deleted"
+    assert "Cleaned up" in prompt.execution_log
+
+
+def test_cleanup_deletes_correlated_todo_stub(tmp_path, manager):  # CLN-002
+    """A 2-byte todo stub whose UUID matches the JSONL file is deleted."""
+    claude_dir, jsonl_dir, todos_dir, *_ = _make_claude_dirs(tmp_path)
+    prompt = _make_prompt()
+
+    _write_file(jsonl_dir / f"{SESSION_UUID}.jsonl", size_bytes=4000)
+    todo_file = todos_dir / f"{SESSION_UUID}-agent-{SESSION_UUID}.json"
+    _write_file(todo_file, content="[]")
+
+    with patch("pathlib.Path.home", return_value=tmp_path):
+        manager.state = QueueState()
+        manager.state.add_prompt(prompt)
+        manager._cleanup_rate_limit_artifacts(prompt)
+
+    assert not todo_file.exists(), "2-byte todo stub should be deleted"
+
+
+def test_cleanup_deletes_correlated_debug_file(tmp_path, manager):  # CLN-003
+    """A debug file whose UUID matches the JSONL file is deleted."""
+    claude_dir, jsonl_dir, todos_dir, debug_dir, _ = _make_claude_dirs(tmp_path)
+    prompt = _make_prompt()
+
+    _write_file(jsonl_dir / f"{SESSION_UUID}.jsonl", size_bytes=4000)
+    debug_file = debug_dir / f"{SESSION_UUID}.txt"
+    _write_file(debug_file, size_bytes=13000)
+
+    with patch("pathlib.Path.home", return_value=tmp_path):
+        manager.state = QueueState()
+        manager.state.add_prompt(prompt)
+        manager._cleanup_rate_limit_artifacts(prompt)
+
+    assert not debug_file.exists(), "Correlated debug file should be deleted"
+
+
+def test_cleanup_deletes_correlated_telemetry_file(tmp_path, manager):  # CLN-004
+    """A telemetry file whose session UUID matches the JSONL file is deleted."""
+    claude_dir, jsonl_dir, _, _, telemetry_dir = _make_claude_dirs(tmp_path)
+    prompt = _make_prompt()
+
+    _write_file(jsonl_dir / f"{SESSION_UUID}.jsonl", size_bytes=4000)
+    telemetry_file = telemetry_dir / f"1p_failed_events.{SESSION_UUID}.{OTHER_UUID}.json"
+    _write_file(telemetry_file, size_bytes=30000)
+
+    with patch("pathlib.Path.home", return_value=tmp_path):
+        manager.state = QueueState()
+        manager.state.add_prompt(prompt)
+        manager._cleanup_rate_limit_artifacts(prompt)
+
+    assert not telemetry_file.exists(), "Correlated telemetry file should be deleted"
+
+
+# ===========================================================================
+# Preservation — Files That Must NOT Be Deleted  (CLN-005 through CLN-009)
+# ===========================================================================
+
+
+def test_cleanup_preserves_old_jsonl(tmp_path, manager):  # CLN-005
+    """JSONL files older than last_executed are not deleted."""
+    claude_dir, jsonl_dir, *_ = _make_claude_dirs(tmp_path)
+
+    old_jsonl = jsonl_dir / f"{SESSION_UUID}.jsonl"
+    _write_file(old_jsonl, size_bytes=4000)
+    # Set mtime to 1 hour ago
+    old_time = time.time() - 3600
+    os.utime(old_jsonl, (old_time, old_time))
+
+    prompt = _make_prompt()
+
+    with patch("pathlib.Path.home", return_value=tmp_path):
+        manager.state = QueueState()
+        manager.state.add_prompt(prompt)
+        manager._cleanup_rate_limit_artifacts(prompt)
+
+    assert old_jsonl.exists(), "Old JSONL file must be preserved"
+
+
+def test_cleanup_preserves_large_jsonl(tmp_path, manager):  # CLN-006
+    """JSONL files >= 10 KB (successful runs) are not deleted even if recent."""
+    claude_dir, jsonl_dir, *_ = _make_claude_dirs(tmp_path)
+    prompt = _make_prompt()
+
+    large_jsonl = jsonl_dir / f"{SESSION_UUID}.jsonl"
+    _write_file(large_jsonl, size_bytes=150_000)  # 150 KB — successful run
+
+    with patch("pathlib.Path.home", return_value=tmp_path):
+        manager.state = QueueState()
+        manager.state.add_prompt(prompt)
+        manager._cleanup_rate_limit_artifacts(prompt)
+
+    assert large_jsonl.exists(), "Large JSONL file (successful run) must be preserved"
+
+
+def test_cleanup_preserves_non_empty_todo(tmp_path, manager):  # CLN-007
+    """Todo files > 2 bytes are not deleted even when UUID-correlated."""
+    claude_dir, jsonl_dir, todos_dir, *_ = _make_claude_dirs(tmp_path)
+    prompt = _make_prompt()
+
+    _write_file(jsonl_dir / f"{SESSION_UUID}.jsonl", size_bytes=4000)
+    real_todo = todos_dir / f"{SESSION_UUID}-agent-{SESSION_UUID}.json"
+    _write_file(real_todo, size_bytes=800)  # legitimate todo
+
+    with patch("pathlib.Path.home", return_value=tmp_path):
+        manager.state = QueueState()
+        manager.state.add_prompt(prompt)
+        manager._cleanup_rate_limit_artifacts(prompt)
+
+    assert real_todo.exists(), "Non-empty todo file must be preserved"
+
+
+def test_cleanup_preserves_old_debug_file(tmp_path, manager):  # CLN-008
+    """Debug files older than last_executed are not deleted even with UUID match."""
+    claude_dir, jsonl_dir, _, debug_dir, _ = _make_claude_dirs(tmp_path)
+
+    # Create JSONL file with current timestamp
+    _write_file(jsonl_dir / f"{SESSION_UUID}.jsonl", size_bytes=4000)
+
+    # Create debug file with old timestamp
+    debug_file = debug_dir / f"{SESSION_UUID}.txt"
+    _write_file(debug_file, size_bytes=13000)
+    old_time = time.time() - 3600
+    os.utime(debug_file, (old_time, old_time))
+
+    prompt = _make_prompt()
+
+    with patch("pathlib.Path.home", return_value=tmp_path):
+        manager.state = QueueState()
+        manager.state.add_prompt(prompt)
+        manager._cleanup_rate_limit_artifacts(prompt)
+
+    assert debug_file.exists(), "Old debug file must be preserved (timestamp guard)"
+
+
+def test_cleanup_does_not_delete_debug_without_jsonl_match(tmp_path, manager):  # CLN-009
+    """Debug files are only deleted when their UUID matches a rate-limited JSONL file.
+
+    If no JSONL file matches (e.g. it's >= 10 KB), the debug file is untouched.
+    """
+    claude_dir, jsonl_dir, _, debug_dir, _ = _make_claude_dirs(tmp_path)
+    prompt = _make_prompt()
+
+    # JSONL file is large (successful run) — no UUID collected
+    _write_file(jsonl_dir / f"{SESSION_UUID}.jsonl", size_bytes=150_000)
+
+    # Debug file exists for same UUID — must NOT be deleted
+    debug_file = debug_dir / f"{SESSION_UUID}.txt"
+    _write_file(debug_file, size_bytes=13000)
+
+    with patch("pathlib.Path.home", return_value=tmp_path):
+        manager.state = QueueState()
+        manager.state.add_prompt(prompt)
+        manager._cleanup_rate_limit_artifacts(prompt)
+
+    assert debug_file.exists(), "Debug file must not be deleted without JSONL UUID match"
+
+
+# ===========================================================================
+# Cleanup Not Triggered for Other Result Types  (CLN-010, CLN-011)
+# ===========================================================================
+
+
+def test_cleanup_not_called_on_success(tmp_path, manager, mocker):  # CLN-010
+    """Successful execution does not trigger artifact cleanup."""
+    prompt = QueuedPrompt(content="task")
+    manager.state = manager.storage.load_queue_state()
+    manager.state.add_prompt(prompt)
+
+    spy = mocker.patch.object(manager, "_cleanup_rate_limit_artifacts")
+
+    success = ExecutionResult(success=True, output="done", error="", execution_time=0.1)
+    mocker.patch.object(manager.claude_interface, "execute_prompt", return_value=success)
+    manager._execute_prompt(prompt)
+
+    spy.assert_not_called()
+
+
+def test_cleanup_not_called_on_generic_failure(tmp_path, manager, mocker):  # CLN-011
+    """Generic failure does not trigger artifact cleanup."""
+    prompt = QueuedPrompt(content="task", max_retries=3)
+    manager.state = manager.storage.load_queue_state()
+    manager.state.add_prompt(prompt)
+
+    spy = mocker.patch.object(manager, "_cleanup_rate_limit_artifacts")
+
+    fail = ExecutionResult(success=False, output="", error="oops", execution_time=0.1)
+    mocker.patch.object(manager.claude_interface, "execute_prompt", return_value=fail)
+    manager._execute_prompt(prompt)
+
+    spy.assert_not_called()
+
+
+def test_cleanup_called_on_rate_limit(tmp_path, manager, mocker):  # CLN-012
+    """Rate-limited execution triggers artifact cleanup."""
+    prompt = QueuedPrompt(content="task", max_retries=3)
+    manager.state = manager.storage.load_queue_state()
+    manager.state.add_prompt(prompt)
+
+    spy = mocker.patch.object(manager, "_cleanup_rate_limit_artifacts")
+
+    mocker.patch.object(
+        manager.claude_interface, "execute_prompt", return_value=_rate_limit_result()
+    )
+    manager._execute_prompt(prompt)
+
+    spy.assert_called_once_with(prompt)
+
+
+# ===========================================================================
+# Missing Directories  (CLN-013)
+# ===========================================================================
+
+
+def test_cleanup_handles_missing_directories(tmp_path, manager):  # CLN-013
+    """Cleanup does not crash when artifact directories don't exist."""
+    # Point home at tmp_path which has no .claude/ at all
+    prompt = _make_prompt()
+    prompt.last_executed = datetime.now()
+
+    with patch("pathlib.Path.home", return_value=tmp_path):
+        manager.state = QueueState()
+        manager.state.add_prompt(prompt)
+        # Should not raise
+        manager._cleanup_rate_limit_artifacts(prompt)
+
+    # No log entry since nothing was deleted
+    assert "Cleaned up" not in prompt.execution_log
+
+
+# ===========================================================================
+# Per-File Exception Handling  (CLN-014)
+# ===========================================================================
+
+
+def test_cleanup_continues_after_oserror_on_one_file(tmp_path, manager, mocker):  # CLN-014
+    """If stat() raises OSError on the debug file, the todo file is still deleted."""
+    _, jsonl_dir, todos_dir, debug_dir, _ = _make_claude_dirs(tmp_path)
+    prompt = _make_prompt()
+
+    # Create one small JSONL
+    _write_file(jsonl_dir / f"{SESSION_UUID}.jsonl", size_bytes=4000)
+
+    # Create debug file normally
+    debug_file = debug_dir / f"{SESSION_UUID}.txt"
+    _write_file(debug_file, size_bytes=13000)
+
+    # Create todo stub — should still be cleaned up despite debug failure
+    todo_file = todos_dir / f"{SESSION_UUID}-agent-{SESSION_UUID}.json"
+    _write_file(todo_file, content="[]")
+
+    # Patch Path.stat to raise OSError only for the debug file
+    original_stat = Path.stat
+
+    def selective_stat(self, *args, **kwargs):
+        if str(self) == str(debug_file):
+            raise OSError("Permission denied")
+        return original_stat(self, *args, **kwargs)
+
+    mocker.patch.object(Path, "stat", selective_stat)
+
+    with patch("pathlib.Path.home", return_value=tmp_path):
+        manager.state = QueueState()
+        manager.state.add_prompt(prompt)
+        manager._cleanup_rate_limit_artifacts(prompt)
+
+    # Stop all mocks before checking file existence (exists() calls stat())
+    mocker.stopall()
+    assert not todo_file.exists(), "Todo file should still be deleted despite debug OSError"
+    assert debug_file.exists(), "Debug file should survive (stat raised OSError)"
+
+
+# ===========================================================================
+# Top-Level Exception Safety  (CLN-015)
+# ===========================================================================
+
+
+def test_cleanup_exception_does_not_break_result_processing(tmp_path, manager, mocker):  # CLN-015
+    """If the entire cleanup throws, _process_execution_result() still completes
+    and the prompt's RATE_LIMITED status is persisted.
+    """
+    prompt = QueuedPrompt(content="task", max_retries=3)
+    manager.state = QueueState()
+    manager.state.add_prompt(prompt)
+
+    # Make cleanup explode
+    mocker.patch.object(
+        manager, "_do_cleanup_rate_limit_artifacts",
+        side_effect=RuntimeError("disk on fire")
+    )
+
+    rl_result = _rate_limit_result()
+    prompt.status = PromptStatus.EXECUTING
+    prompt.last_executed = datetime.now()
+    manager._process_execution_result(prompt, rl_result)
+
+    assert prompt.status == PromptStatus.RATE_LIMITED, (
+        "Prompt must reach RATE_LIMITED status even when cleanup throws"
+    )
+    assert manager.state.last_processed is not None, (
+        "last_processed must be set even when cleanup throws"
+    )
+    assert "artifact cleanup failed" in prompt.execution_log
+
+
+# ===========================================================================
+# No last_executed Guard  (CLN-016)
+# ===========================================================================
+
+
+def test_cleanup_noop_without_last_executed(manager):  # CLN-016
+    """Cleanup is a no-op when prompt.last_executed is None."""
+    prompt = QueuedPrompt(content="task")
+    prompt.last_executed = None
+
+    manager.state = QueueState()
+    manager.state.add_prompt(prompt)
+
+    # Should not raise and should not log
+    manager._cleanup_rate_limit_artifacts(prompt)
+    assert "Cleaned up" not in prompt.execution_log
+
+
+# ===========================================================================
+# Resolved Working Directory  (CLN-017, CLN-018)
+# ===========================================================================
+
+
+def test_execute_prompt_stashes_resolved_working_directory(manager, mocker):  # CLN-017
+    """_execute_prompt() sets _resolved_working_directory on the prompt."""
+    prompt = QueuedPrompt(content="task", working_directory="/some/path")
+    manager.state = manager.storage.load_queue_state()
+    manager.state.add_prompt(prompt)
+
+    mocker.patch.object(
+        manager.claude_interface, "execute_prompt",
+        return_value=ExecutionResult(success=True, output="ok", error="", execution_time=0.1),
+    )
+    manager._execute_prompt(prompt)
+
+    assert prompt._resolved_working_directory is not None
+    assert prompt._resolved_working_directory == str(Path("/some/path").resolve())
+
+
+def test_cleanup_uses_resolved_working_directory(tmp_path, manager):  # CLN-018
+    """Cleanup uses _resolved_working_directory (not re-resolving working_directory)."""
+    # Set up dirs for the resolved path, not the relative one
+    claude_dir, jsonl_dir, *_ = _make_claude_dirs(tmp_path, working_dir=FAKE_WORKING_DIR)
+
+    prompt = QueuedPrompt(
+        content="task",
+        working_directory=".",  # relative — would resolve to CWD
+        status=PromptStatus.EXECUTING,
+    )
+    prompt.last_executed = datetime.now() - timedelta(seconds=1)
+    prompt._resolved_working_directory = FAKE_WORKING_DIR  # stashed at execution time
+
+    jsonl_file = jsonl_dir / f"{SESSION_UUID}.jsonl"
+    _write_file(jsonl_file, size_bytes=4000)
+
+    with patch("pathlib.Path.home", return_value=tmp_path):
+        manager.state = QueueState()
+        manager.state.add_prompt(prompt)
+        manager._cleanup_rate_limit_artifacts(prompt)
+
+    assert not jsonl_file.exists(), (
+        "Cleanup must use _resolved_working_directory, not re-resolve '.'"
+    )
+
+
+# ===========================================================================
+# Deleted Count and Logging  (CLN-019)
+# ===========================================================================
+
+
+def test_cleanup_counts_all_deleted_artifacts(tmp_path, manager, capsys):  # CLN-019
+    """The deleted count includes all four artifact types."""
+    claude_dir, jsonl_dir, todos_dir, debug_dir, telemetry_dir = _make_claude_dirs(tmp_path)
+    prompt = _make_prompt()
+
+    _write_file(jsonl_dir / f"{SESSION_UUID}.jsonl", size_bytes=4000)
+    _write_file(todos_dir / f"{SESSION_UUID}-agent-{SESSION_UUID}.json", content="[]")
+    _write_file(debug_dir / f"{SESSION_UUID}.txt", size_bytes=13000)
+    _write_file(telemetry_dir / f"1p_failed_events.{SESSION_UUID}.{OTHER_UUID}.json", size_bytes=30000)
+
+    with patch("pathlib.Path.home", return_value=tmp_path):
+        manager.state = QueueState()
+        manager.state.add_prompt(prompt)
+        manager._cleanup_rate_limit_artifacts(prompt)
+
+    assert "Cleaned up 4 rate-limit artifact(s)" in prompt.execution_log
+    captured = capsys.readouterr()
+    assert "[cleanup] Removed 4 rate-limit artifact(s)" in captured.out
+
+
+def test_cleanup_no_log_when_nothing_deleted(tmp_path, manager, capsys):  # CLN-020
+    """No log entry or print when zero files are deleted."""
+    _make_claude_dirs(tmp_path)
+    prompt = _make_prompt()
+
+    with patch("pathlib.Path.home", return_value=tmp_path):
+        manager.state = QueueState()
+        manager.state.add_prompt(prompt)
+        manager._cleanup_rate_limit_artifacts(prompt)
+
+    assert "Cleaned up" not in prompt.execution_log
+    captured = capsys.readouterr()
+    assert "[cleanup]" not in captured.out
+
+
+# ===========================================================================
+# JSONL Early Break  (CLN-021)
+# ===========================================================================
+
+
+def test_cleanup_breaks_after_first_jsonl_match(tmp_path, manager):  # CLN-021
+    """Only one JSONL file is deleted per cleanup (one subprocess = one UUID).
+
+    Even with multiple small recent JSONL files, only the first match is deleted.
+    """
+    uuid2 = "99999999-aaaa-bbbb-cccc-dddddddddddd"
+    claude_dir, jsonl_dir, *_ = _make_claude_dirs(tmp_path)
+    prompt = _make_prompt()
+
+    f1 = jsonl_dir / f"{SESSION_UUID}.jsonl"
+    f2 = jsonl_dir / f"{uuid2}.jsonl"
+    _write_file(f1, size_bytes=4000)
+    _write_file(f2, size_bytes=4000)
+
+    with patch("pathlib.Path.home", return_value=tmp_path):
+        manager.state = QueueState()
+        manager.state.add_prompt(prompt)
+        manager._cleanup_rate_limit_artifacts(prompt)
+
+    # Exactly one should be deleted (we don't know which due to glob ordering)
+    remaining = list(jsonl_dir.glob("*.jsonl"))
+    assert len(remaining) == 1, (
+        f"Expected exactly 1 JSONL file remaining after cleanup, got {len(remaining)}"
+    )
+
+
+# ===========================================================================
+# _resolved_working_directory Field  (CLN-022)
+# ===========================================================================
+
+
+def test_resolved_working_directory_not_persisted_to_yaml(tmp_path, manager):  # CLN-022
+    """_resolved_working_directory is transient and not written to YAML frontmatter."""
+    prompt = QueuedPrompt(content="task", working_directory="/some/path")
+    prompt._resolved_working_directory = "/some/path"
+    prompt.last_executed = datetime.now()
+
+    manager.state = manager.storage.load_queue_state()
+    manager.state.add_prompt(prompt)
+    manager.storage.save_queue_state(manager.state)
+
+    # Read the file back and check YAML doesn't contain the field
+    queue_files = list(manager.storage.queue_dir.glob("*.md"))
+    assert len(queue_files) == 1
+    content = queue_files[0].read_text()
+    assert "_resolved_working_directory" not in content
+
+    # Reload and verify it's None (not persisted)
+    reloaded = manager.storage.load_queue_state()
+    reloaded_prompt = reloaded.prompts[0]
+    assert reloaded_prompt._resolved_working_directory is None
+
+
+# ===========================================================================
+# Fallback When _resolved_working_directory Is None  (CLN-023)
+# ===========================================================================
+
+
+def test_cleanup_falls_back_to_resolve_when_stash_missing(tmp_path, manager):  # CLN-023
+    """If _resolved_working_directory is None, cleanup resolves working_directory directly."""
+    claude_dir, jsonl_dir, *_ = _make_claude_dirs(tmp_path, working_dir=FAKE_WORKING_DIR)
+    prompt = QueuedPrompt(
+        content="task",
+        working_directory=FAKE_WORKING_DIR,
+        status=PromptStatus.EXECUTING,
+    )
+    prompt.last_executed = datetime.now() - timedelta(seconds=1)
+    prompt._resolved_working_directory = None  # simulate missing stash
+
+    jsonl_file = jsonl_dir / f"{SESSION_UUID}.jsonl"
+    _write_file(jsonl_file, size_bytes=4000)
+
+    with patch("pathlib.Path.home", return_value=tmp_path):
+        manager.state = QueueState()
+        manager.state.add_prompt(prompt)
+        manager._cleanup_rate_limit_artifacts(prompt)
+
+    assert not jsonl_file.exists(), "Cleanup should fall back to resolving working_directory"