diff --git a/litellm-proxy-extras/litellm_proxy_extras/utils.py b/litellm-proxy-extras/litellm_proxy_extras/utils.py
index 7eff0c00f75..cdc8c95972a 100644
--- a/litellm-proxy-extras/litellm_proxy_extras/utils.py
+++ b/litellm-proxy-extras/litellm_proxy_extras/utils.py
@@ -234,7 +234,6 @@ class ProxyExtrasDBManager:
             r"duplicate key value violates",
             r"relation .* already exists",
             r"constraint .* already exists",
-            r"does not exist",
             r"Can't drop database.* because it doesn't exist",
         ]
 
@@ -326,9 +325,20 @@ class ProxyExtrasDBManager:
             logger.info(f"prisma db execute stdout: {result.stdout}")
             logger.info("✅ Migration diff applied successfully")
         except subprocess.CalledProcessError as e:
-            logger.warning(f"Failed to apply migration diff: {e.stderr}")
+            logger.error(
+                f"Failed to apply migration diff: {e.stderr}. "
+                f"Will NOT mark migrations as applied."
+            )
+            raise RuntimeError(
+                f"Migration diff application failed. Migrations will not be marked as applied. "
+                f"Please check the database state and apply the diff manually. Error: {e.stderr}"
+            ) from e
         except subprocess.TimeoutExpired:
-            logger.warning("Migration diff application timed out.")
+            logger.error("Migration diff application timed out. Will NOT mark migrations as applied.")
+            raise RuntimeError(
+                "Migration diff application timed out. Migrations will not be marked as applied. "
+                "Please check the database state and apply the diff manually."
+            )
 
         # 3. Mark all migrations as applied
         if not mark_all_applied:
diff --git a/tests/litellm-proxy-extras/test_litellm_proxy_extras_utils.py b/tests/litellm-proxy-extras/test_litellm_proxy_extras_utils.py
index c1e3fd5072f..1d610633664 100644
--- a/tests/litellm-proxy-extras/test_litellm_proxy_extras_utils.py
+++ b/tests/litellm-proxy-extras/test_litellm_proxy_extras_utils.py
@@ -109,9 +109,19 @@ class TestIdempotentErrorDetection:
         error_message = "constraint 'fk_user_id' already exists"
         assert ProxyExtrasDBManager._is_idempotent_error(error_message) is True
 
-    def test_is_idempotent_error_does_not_exist(self):
-        """Test detection of 'does not exist' error"""
+    def test_is_idempotent_error_does_not_exist_is_not_idempotent(self):
+        """Generic 'does not exist' errors are NOT idempotent — they indicate real failures"""
         error_message = "ERROR: index 'idx' does not exist"
+        assert ProxyExtrasDBManager._is_idempotent_error(error_message) is False
+
+    def test_is_idempotent_error_relation_does_not_exist_is_not_idempotent(self):
+        """Relation 'does not exist' errors are NOT idempotent"""
+        error_message = 'ERROR: relation "LiteLLM_DailyAgentSpend" does not exist'
+        assert ProxyExtrasDBManager._is_idempotent_error(error_message) is False
+
+    def test_is_idempotent_error_cant_drop_database_is_idempotent(self):
+        """Can't drop database because it doesn't exist IS idempotent"""
+        error_message = "Can't drop database 'litellm' because it doesn't exist"
         assert ProxyExtrasDBManager._is_idempotent_error(error_message) is True
 
     def test_is_idempotent_error_case_insensitive(self):
@@ -119,11 +129,6 @@ class TestIdempotentErrorDetection:
         error_message = "COLUMN 'ID' ALREADY EXISTS"
         assert ProxyExtrasDBManager._is_idempotent_error(error_message) is True
 
-    def test_is_idempotent_error_does_not_exist(self):
-        """Test detection of 'does not exist' error"""
-        error_message = "ERROR: index 'idx' does not exist"
-        assert ProxyExtrasDBManager._is_idempotent_error(error_message) is True
-
     def test_is_idempotent_error_negative(self):
         """Test that non-idempotent errors are not detected as idempotent errors"""
         error_message = "Database error code: 42501 - permission denied"