diff --git a/tests/unit/test_fee_payout_crash_safety.py b/tests/unit/test_fee_payout_crash_safety.py
index 04206b70..0939baa4 100644
--- a/tests/unit/test_fee_payout_crash_safety.py
+++ b/tests/unit/test_fee_payout_crash_safety.py
@@ -91,6 +91,38 @@ async def test_fee_payout_checkpoints_before_sending() -> None:
     assert events == ["checkpoint", "send", "complete"]
 
 
+@pytest.mark.asyncio
+async def test_fee_payout_does_not_retry_an_unresolved_checkpoint() -> None:
+    session = Mock()
+    fee = SimpleNamespace(
+        accumulated_msats=10_000,
+        payout_in_progress_msats=5_000,
+        payout_started_at=123,
+    )
+
+    with (
+        patch("routstr.auth.ROUTSTR_FEE_PAYOUT_INTERVAL_SECONDS", 1),
+        patch("routstr.auth.ROUTSTR_LN_ADDRESS", "fees@example.com"),
+        patch(
+            "routstr.wallet.asyncio.sleep",
+            AsyncMock(side_effect=[None, asyncio.CancelledError()]),
+        ),
+        patch("routstr.wallet.db.create_session", return_value=_session_context(session)),
+        patch("routstr.wallet.db.get_routstr_fee", AsyncMock(return_value=fee)),
+        patch("routstr.wallet.db.reset_routstr_fee", AsyncMock()) as checkpoint,
+        patch("routstr.wallet.get_wallet", AsyncMock()) as get_wallet,
+        patch("routstr.wallet.raw_send_to_lnurl", AsyncMock()) as send,
+        patch("routstr.wallet.logger.critical") as critical,
+    ):
+        with pytest.raises(asyncio.CancelledError):
+            await wallet.periodic_routstr_fee_payout()
+
+    checkpoint.assert_not_awaited()
+    get_wallet.assert_not_awaited()
+    send.assert_not_awaited()
+    critical.assert_called_once()
+
+
 @pytest.mark.asyncio
 async def test_fee_payout_keeps_checkpoint_when_send_outcome_is_unknown() -> None:
     session = Mock()
diff --git a/tests/unit/test_fee_payout_migration.py b/tests/unit/test_fee_payout_migration.py
new file mode 100644
index 00000000..fe549194
--- /dev/null
+++ b/tests/unit/test_fee_payout_migration.py
@@ -0,0 +1,46 @@
+import os
+import sqlite3
+import subprocess
+import sys
+from pathlib import Path
+
+
+def _run_alembic(root: Path, database_url: str, revision: str) -> None:
+    env = os.environ.copy()
+    env["DATABASE_URL"] = database_url
+    subprocess.run(
+        [sys.executable, "-m", "alembic", "upgrade", revision],
+        cwd=root,
+        env=env,
+        check=True,
+        capture_output=True,
+        text=True,
+    )
+
+
+def test_fee_payout_checkpoint_migration_preserves_existing_row(
+    tmp_path: Path,
+) -> None:
+    root = Path(__file__).resolve().parents[2]
+    database_path = tmp_path / "migration.db"
+    database_url = f"sqlite+aiosqlite:///{database_path}"
+    _run_alembic(root, database_url, "c6d7e8f9a0b1")
+
+    with sqlite3.connect(database_path) as connection:
+        result = connection.execute(
+            "UPDATE routstr_fees SET accumulated_msats = 5000, "
+            "total_paid_msats = 1000, last_paid_at = 123 WHERE id = 1"
+        )
+        assert result.rowcount == 1
+        connection.commit()
+
+    _run_alembic(root, database_url, "head")
+
+    with sqlite3.connect(database_path) as connection:
+        row = connection.execute(
+            "SELECT accumulated_msats, total_paid_msats, last_paid_at, "
+            "payout_in_progress_msats, payout_started_at "
+            "FROM routstr_fees WHERE id = 1"
+        ).fetchone()
+
+    assert row == (5000, 1000, 123, 0, None)