diff --git a/tests/test_litellm/_fixture_recorder.py b/tests/test_litellm/_fixture_recorder.py
index a2d4ed06bbc..849efd15040 100644
--- a/tests/test_litellm/_fixture_recorder.py
+++ b/tests/test_litellm/_fixture_recorder.py
@@ -12,6 +12,7 @@ from pathlib import Path
 from typing import Final, cast
 
 import httpx
+from pydantic import ValidationError
 
 from tests.test_litellm._json_fs_cache import JsonFileCache, canonical_json
 from tests.test_litellm.ocr.fixture_models import (
@@ -194,7 +195,17 @@ def fixture_directory(configured: Path | None, env_value: str | None, default: P
 
 
 def recorded_fixtures(directory: Path) -> tuple[OcrParityCase, ...]:
-    return tuple(OcrParityCase.model_validate(raw_fixture) for raw_fixture in JsonFileCache(directory).values())
+    cache: Final = JsonFileCache(directory)
+    fixtures: list[OcrParityCase] = []
+    for path, raw_fixture in cache.values_with_paths():
+        try:
+            fixtures.append(OcrParityCase.model_validate(raw_fixture))
+        except ValidationError as error:
+            raise ValueError(
+                f"invalid OCR parity fixture {path}: expected exactly `input` and `upstream_response` "
+                f"({len(error.errors())} validation errors)"
+            ) from error
+    return tuple(fixtures)
 
 
 def fixture_id(fixture: OcrParityCase) -> str:
diff --git a/tests/test_litellm/_json_fs_cache.py b/tests/test_litellm/_json_fs_cache.py
index 9ce43931e36..dfc8b6331f4 100644
--- a/tests/test_litellm/_json_fs_cache.py
+++ b/tests/test_litellm/_json_fs_cache.py
@@ -43,3 +43,9 @@ class JsonFileCache:
             return ()
         paths: Final = tuple(sorted(self.root.rglob("*.json")))
         return tuple(JSON_OBJECT.validate_json(path.read_text(encoding="utf-8")) for path in paths)
+
+    def values_with_paths(self) -> tuple[tuple[Path, dict[str, object]], ...]:
+        if not self.root.is_dir():
+            return ()
+        paths: Final = tuple(sorted(self.root.rglob("*.json")))
+        return tuple((path, JSON_OBJECT.validate_json(path.read_text(encoding="utf-8"))) for path in paths)
diff --git a/tests/test_litellm/ocr/conftest.py b/tests/test_litellm/ocr/conftest.py
index 2822efe23ad..b5410325905 100644
--- a/tests/test_litellm/ocr/conftest.py
+++ b/tests/test_litellm/ocr/conftest.py
@@ -5,6 +5,7 @@ from pathlib import Path
 from typing import Final
 
 import pytest
+from pydantic import ValidationError
 
 from tests.test_litellm._fixture_recorder import fixture_id, recorded_fixtures
 
@@ -23,16 +24,26 @@ def _fixture_directory() -> Path:
 def pytest_generate_tests(metafunc: pytest.Metafunc) -> None:
     if "ocr_fixture" not in metafunc.fixturenames:
         return
-    fixtures: Final = recorded_fixtures(_fixture_directory())
+    directory: Final = _fixture_directory()
+    try:
+        fixtures: Final = recorded_fixtures(directory)
+    except (ValidationError, ValueError) as error:
+        raise pytest.UsageError(
+            f"Invalid OCR parity fixture bundle at {directory}. "
+            "Each fixture must contain exactly `input` and `upstream_response`. "
+            "Record fresh fixtures in an empty directory with: "
+            f"`uv run python tests/test_litellm/ocr/generate_fixtures.py --fixture-dir {directory}`. "
+            f"Validation details: {error}"
+        ) from error
     if not fixtures:
         if FIXTURE_DIR_ENV in os.environ:
-            raise pytest.UsageError(f"no recorded OCR fixtures in {_fixture_directory()}")
+            raise pytest.UsageError(f"no recorded OCR fixtures in {directory}")
         metafunc.parametrize(
             "ocr_fixture",
             (
                 pytest.param(
                     None,
-                    marks=pytest.mark.skip(reason=f"no recorded OCR fixtures in {_fixture_directory()}"),
+                    marks=pytest.mark.skip(reason=f"no recorded OCR fixtures in {directory}"),
                     id="no-recorded-fixtures",
                 ),
             ),