diff --git a/litellm/proxy/guardrails/guardrail_registry.py b/litellm/proxy/guardrails/guardrail_registry.py
index 5ba71a7fa12..13bfc675a01 100644
--- a/litellm/proxy/guardrails/guardrail_registry.py
+++ b/litellm/proxy/guardrails/guardrail_registry.py
@@ -141,27 +141,33 @@ def guardrail_from_db_row(row: Iterable[tuple[str, object]]) -> Guardrail:
 
 
 async def _rotate_guardrail_row(
-    prisma_client: PrismaClient, row: "prisma_models.LiteLLM_GuardrailsTable", encryption_key: str
+    prisma_client: PrismaClient,
+    row: "prisma_models.LiteLLM_GuardrailsTable | None",
+    encryption_key: str,
+    attempts_left: int = GUARDRAIL_ROTATION_ATTEMPTS,
 ) -> int:
-    current: prisma_models.LiteLLM_GuardrailsTable | None = row
-    for _ in range(GUARDRAIL_ROTATION_ATTEMPTS):
-        if current is None or not isinstance(current.litellm_params, Mapping):
-            return 0
-        rotated_params: dict[str, object] = encrypt_guardrail_litellm_params(
-            decrypt_guardrail_litellm_params(current.litellm_params), new_encryption_key=encryption_key
-        )
-        if rotated_params == current.litellm_params:
-            return 0
-        if await _guardrail_table(prisma_client).update_many(
-            where={"guardrail_id": current.guardrail_id, "updated_at": current.updated_at},
-            data={"litellm_params": safe_dumps(rotated_params)},
-        ):
-            return 1
-        current = await _guardrail_table(prisma_client).find_unique(where={"guardrail_id": row.guardrail_id})
-    verbose_proxy_logger.warning(
-        "Guardrail %s kept changing during master key rotation; its secrets were not re-encrypted", row.guardrail_id
+    """Re-encrypt one row's params under encryption_key with a compare-and-set on updated_at.
+    A row edited since it was read is re-read and retried, up to attempts_left writes. Returns 1 when rewritten."""
+    if row is None or not isinstance(row.litellm_params, Mapping):
+        return 0
+    rotated_params: Final = encrypt_guardrail_litellm_params(
+        decrypt_guardrail_litellm_params(row.litellm_params), new_encryption_key=encryption_key
     )
-    return 0
+    if rotated_params == row.litellm_params:
+        return 0
+    if await _guardrail_table(prisma_client).update_many(
+        where={"guardrail_id": row.guardrail_id, "updated_at": row.updated_at},
+        data={"litellm_params": safe_dumps(rotated_params)},
+    ):
+        return 1
+    if attempts_left <= 1:
+        verbose_proxy_logger.warning(
+            "Guardrail %s kept changing during master key rotation; its secrets were not re-encrypted",
+            row.guardrail_id,
+        )
+        return 0
+    latest_row: Final = await _guardrail_table(prisma_client).find_unique(where={"guardrail_id": row.guardrail_id})
+    return await _rotate_guardrail_row(prisma_client, latest_row, encryption_key, attempts_left - 1)
 
 
 guardrail_initializer_registry: Final = {
diff --git a/tests/code_coverage_tests/recursive_detector.py b/tests/code_coverage_tests/recursive_detector.py
index 9a4860a7977..9667156d3a8 100644
--- a/tests/code_coverage_tests/recursive_detector.py
+++ b/tests/code_coverage_tests/recursive_detector.py
@@ -38,6 +38,7 @@ IGNORE_FUNCTIONS = [
     "_mask_sequence",  # max depth set.
     "_encrypted_param",  # max depth set.
     "_decrypted_param",  # max depth set.
+    "_rotate_guardrail_row",  # bounded by attempts_left.
     "_delete_nested_value_custom",  # max depth set (bounded by number of path segments).
     "filter_exceptions_from_params",  # max depth set (default 20) to prevent infinite recursion.
     "__getattr__",  # lazy loading pattern in litellm/__init__.py with proper caching to prevent infinite recursion.
diff --git a/tests/test_litellm/proxy/guardrails/test_guardrail_registry.py b/tests/test_litellm/proxy/guardrails/test_guardrail_registry.py
index 45955270d5d..08b099cc9ef 100644
--- a/tests/test_litellm/proxy/guardrails/test_guardrail_registry.py
+++ b/tests/test_litellm/proxy/guardrails/test_guardrail_registry.py
@@ -1293,3 +1293,25 @@ async def test_rotate_guardrail_params_retries_a_row_edited_during_rotation(monk
     assert decrypt_guardrail_litellm_params(_stored_params(prisma_client.db.litellm_guardrailstable.update_many)) == {
         "api_key": "edited-key"
     }
+
+
+@pytest.mark.asyncio
+async def test_rotate_guardrail_params_gives_up_on_a_row_that_keeps_changing(monkeypatch):
+    from litellm.constants import GUARDRAIL_ROTATION_ATTEMPTS
+    from litellm.proxy.guardrails.guardrail_registry import encrypt_guardrail_litellm_params
+
+    monkeypatch.delenv("LITELLM_SALT_KEY", raising=False)
+    monkeypatch.setattr("litellm.proxy.proxy_server.master_key", "sk-old-master")
+    row = _Row(guardrail_id="g-1", updated_at="t1", litellm_params=encrypt_guardrail_litellm_params({"api_key": "k"}))
+    prisma_client = MagicMock()
+    prisma_client.db.litellm_guardrailstable.find_many = AsyncMock(return_value=[row])
+    prisma_client.db.litellm_guardrailstable.find_unique = AsyncMock(return_value=row)
+    prisma_client.db.litellm_guardrailstable.update_many = AsyncMock(return_value=0)
+
+    rows_updated = await GuardrailRegistry.rotate_guardrail_params_master_key(
+        prisma_client=prisma_client, new_master_key="sk-new-master"
+    )
+
+    assert rows_updated == 0
+    assert prisma_client.db.litellm_guardrailstable.update_many.await_count == GUARDRAIL_ROTATION_ATTEMPTS
+    assert prisma_client.db.litellm_guardrailstable.find_unique.await_count == GUARDRAIL_ROTATION_ATTEMPTS - 1