diff --git a/machine-learning/app/main.py b/machine-learning/app/main.py
index 3c607015d92ea..ac493a059a013 100644
--- a/machine-learning/app/main.py
+++ b/machine-learning/app/main.py
@@ -192,23 +192,18 @@ async def load(model: InferenceModel) -> InferenceModel:
         return model
 
     def _load(model: InferenceModel) -> InferenceModel:
+        if model.load_attempts > 1:
+            raise HTTPException(500, f"Failed to load model '{model.model_name}'")
         with lock:
             model.load()
         return model
 
     try:
-        await run(_load, model)
-        return model
+        return await run(_load, model)
     except (OSError, InvalidProtobuf, BadZipFile, NoSuchFile):
-        log.warning(
-            (
-                f"Failed to load {model.model_type.replace('_', ' ')} model '{model.model_name}'."
-                "Clearing cache and retrying."
-            )
-        )
+        log.warning(f"Failed to load {model.model_type.replace('_', ' ')} model '{model.model_name}'. Clearing cache.")
         model.clear_cache()
-        await run(_load, model)
-        return model
+        return await run(_load, model)
 
 
 async def idle_shutdown_task() -> None:
diff --git a/machine-learning/app/models/base.py b/machine-learning/app/models/base.py
index f64a873010115..4ad6fd6eb7049 100644
--- a/machine-learning/app/models/base.py
+++ b/machine-learning/app/models/base.py
@@ -31,6 +31,7 @@ def __init__(
         **model_kwargs: Any,
     ) -> None:
         self.loaded = False
+        self.load_attempts = 0
         self.model_name = clean_name(model_name)
         self.cache_dir = Path(cache_dir) if cache_dir is not None else self.cache_dir_default
         self.providers = providers if providers is not None else self.providers_default
@@ -48,9 +49,11 @@ def download(self) -> None:
     def load(self) -> None:
         if self.loaded:
             return
+        self.load_attempts += 1
 
         self.download()
-        log.info(f"Loading {self.model_type.replace('-', ' ')} model '{self.model_name}' to memory")
+        attempt = f"Attempt #{self.load_attempts + 1} to load" if self.load_attempts else "Loading"
+        log.info(f"{attempt} {self.model_type.replace('-', ' ')} model '{self.model_name}' to memory")
         self.session = self._load()
         self.loaded = True
 
diff --git a/machine-learning/app/test_main.py b/machine-learning/app/test_main.py
index d9d1455bd1cda..2068c7a4c6856 100644
--- a/machine-learning/app/test_main.py
+++ b/machine-learning/app/test_main.py
@@ -11,6 +11,7 @@
 import numpy as np
 import onnxruntime as ort
 import pytest
+from fastapi import HTTPException
 from fastapi.testclient import TestClient
 from PIL import Image
 from pytest import MonkeyPatch
@@ -627,6 +628,7 @@ class TestLoad:
     async def test_load(self) -> None:
         mock_model = mock.Mock(spec=InferenceModel)
         mock_model.loaded = False
+        mock_model.load_attempts = 0
 
         res = await load(mock_model)
 
@@ -650,6 +652,7 @@ async def test_load_clears_cache_and_retries_if_os_error(self) -> None:
         mock_model.model_task = ModelTask.SEARCH
         mock_model.load.side_effect = [OSError, None]
         mock_model.loaded = False
+        mock_model.load_attempts = 0
 
         res = await load(mock_model)
 
@@ -657,6 +660,20 @@ async def test_load_clears_cache_and_retries_if_os_error(self) -> None:
         mock_model.clear_cache.assert_called_once()
         assert mock_model.load.call_count == 2
 
+    async def test_load_clears_cache_and_raises_if_os_error_and_already_retried(self) -> None:
+        mock_model = mock.Mock(spec=InferenceModel)
+        mock_model.model_name = "test_model_name"
+        mock_model.model_type = ModelType.VISUAL
+        mock_model.model_task = ModelTask.SEARCH
+        mock_model.loaded = False
+        mock_model.load_attempts = 2
+
+        with pytest.raises(HTTPException):
+            await load(mock_model)
+
+        mock_model.clear_cache.assert_not_called()
+        mock_model.load.assert_not_called()
+
 
 @pytest.mark.skipif(
     not settings.test_full,