diff --git a/backend/models/databases/supabase/brains.py b/backend/models/databases/supabase/brains.py
index 959aafbaa..8422e3294 100644
--- a/backend/models/databases/supabase/brains.py
+++ b/backend/models/databases/supabase/brains.py
@@ -278,36 +278,39 @@ class Brain(Repository):
 
     def delete_file_from_brain(self, brain_id, file_name: str):
         # First, get the vector_ids associated with the file_name
-        vector_response = (
+        file_vectors = (
             self.db.table("vectors")
             .select("id")
             .filter("metadata->>file_name", "eq", file_name)
             .execute()
         )
-        vector_ids = [item["id"] for item in vector_response.data]
 
-        # For each vector_id, delete the corresponding entry from the 'brains_vectors' table
-        for vector_id in vector_ids:
-            self.db.table("brains_vectors").delete().filter(
-                "vector_id", "eq", vector_id
-            ).filter("brain_id", "eq", brain_id).execute()
+        file_vectors_ids = [item["id"] for item in file_vectors.data]
 
-            # Check if the vector is still associated with any other brains
-            associated_brains_response = (
-                self.db.table("brains_vectors")
-                .select("brain_id")
-                .filter("vector_id", "eq", vector_id)
-                .execute()
-            )
-            associated_brains = [
-                item["brain_id"] for item in associated_brains_response.data
-            ]
+        # remove current file vectors from brain vectors
+        self.db.table("brains_vectors").delete().filter(
+            "vector_id", "in", file_vectors_ids
+        ).filter("brain_id", "eq", brain_id).execute()
 
-            # If the vector is not associated with any other brains, delete it from 'vectors' table
-            if not associated_brains:
-                self.db.table("vectors").delete().filter(
-                    "id", "eq", vector_id
-                ).execute()
+        vectors_used_by_another_brain = (
+            self.db.table("brains_vectors")
+            .select("vector_id")
+            .filter("vector_id", "in", file_vectors_ids)
+            .filter("brain_id", "neq", brain_id)
+            .execute()
+        )
+
+        vectors_used_by_another_brain_ids = [
+            item["vector_id"] for item in vectors_used_by_another_brain.data
+        ]
+
+        vectors_no_longer_used_ids = [
+            id for id in file_vectors_ids if id not in vectors_used_by_another_brain_ids
+        ]
+
+        self.db.table("vectors").delete().filter(
+            "id", "in", vectors_no_longer_used_ids
+        ).execute()
 
         return {"message": f"File {file_name} in brain {brain_id} has been deleted."}
 
diff --git a/backend/routes/knowledge_routes.py b/backend/routes/knowledge_routes.py
index 0cf82525e..fa4ca43fe 100644
--- a/backend/routes/knowledge_routes.py
+++ b/backend/routes/knowledge_routes.py
@@ -1,6 +1,6 @@
 from uuid import UUID
 
-from fastapi import APIRouter, Depends, Query
+from fastapi import APIRouter, Depends, HTTPException, Query
 from logger import get_logger
 from middlewares.auth import AuthBearer, get_current_user
 from models import Brain
@@ -10,6 +10,7 @@ from repository.files.generate_file_signed_url import generate_file_signed_url
 from repository.knowledge.get_all_knowledge import get_all_knowledge
 from repository.knowledge.get_knowledge import get_knowledge
 from repository.knowledge.remove_knowledge import remove_knowledge
+
 from routes.authorizations.brain_authorization import (
     RoleEnum,
     has_brain_authorization,
@@ -56,8 +57,6 @@ async def delete_endpoint(
     Delete a specific knowledge from a brain.
     """
 
-    validate_brain_authorization(brain_id=brain_id, user_id=current_user.id)
-
     brain = Brain(id=brain_id)
 
     knowledge = get_knowledge(knowledge_id)
@@ -93,7 +92,10 @@ async def generate_signed_url_endpoint(
     validate_brain_authorization(brain_id=knowledge.brain_id, user_id=current_user.id)
 
     if knowledge.file_name == None:
-        raise Exception(f"Knowledge {knowledge_id} has no file_name associated with it")
+        raise HTTPException(
+            status_code=404,
+            detail=f"Knowledge with id {knowledge_id} is not a file.",
+        )
 
     file_path_in_storage = f"{knowledge.brain_id}/{knowledge.file_name}"