diff --git a/src/backend/core/api/viewsets.py b/src/backend/core/api/viewsets.py
index 799b8374..0a5ee4cc 100644
--- a/src/backend/core/api/viewsets.py
+++ b/src/backend/core/api/viewsets.py
@@ -41,7 +41,7 @@ UUID_REGEX = (
 FILE_EXT_REGEX = r"\.[a-zA-Z0-9]{1,10}"
 MEDIA_STORAGE_URL_PATTERN = re.compile(
     f"{settings.MEDIA_URL:s}(?P<pk>{UUID_REGEX:s})/"
-    f"(?P<key>{ATTACHMENTS_FOLDER:s}/{UUID_REGEX:s}{FILE_EXT_REGEX:s})$"
+    f"(?P<key>{ATTACHMENTS_FOLDER:s}/{UUID_REGEX:s}(?:-unsafe)?{FILE_EXT_REGEX:s})$"
 )
 COLLABORATION_WS_URL_PATTERN = re.compile(rf"(?:^|&)room=(?P<pk>{UUID_REGEX})(?:&|$)")
 
@@ -915,15 +915,18 @@ class DocumentViewSet(
         # Generate a generic yet unique filename to store the image in object storage
         file_id = uuid.uuid4()
         extension = serializer.validated_data["expected_extension"]
-        key = f"{document.key_base}/{ATTACHMENTS_FOLDER:s}/{file_id!s}.{extension:s}"
 
         # Prepare metadata for storage
         extra_args = {
             "Metadata": {"owner": str(request.user.id)},
             "ContentType": serializer.validated_data["content_type"],
         }
+        file_unsafe = ""
         if serializer.validated_data["is_unsafe"]:
             extra_args["Metadata"]["is_unsafe"] = "true"
+            file_unsafe = "-unsafe"
+
+        key = f"{document.key_base}/{ATTACHMENTS_FOLDER:s}/{file_id!s}{file_unsafe}.{extension:s}"
 
         file = serializer.validated_data["file"]
         default_storage.connection.meta.client.upload_fileobj(
diff --git a/src/backend/core/tests/documents/test_api_documents_attachment_upload.py b/src/backend/core/tests/documents/test_api_documents_attachment_upload.py
index 4a6564d6..de8d3dca 100644
--- a/src/backend/core/tests/documents/test_api_documents_attachment_upload.py
+++ b/src/backend/core/tests/documents/test_api_documents_attachment_upload.py
@@ -291,7 +291,9 @@ def test_api_documents_attachment_upload_fix_extension(
     match = pattern.search(file_path)
     file_id = match.group(1)
 
+    assert "-unsafe" in file_id
     # Validate that file_id is a valid UUID
+    file_id = file_id.replace("-unsafe", "")
     uuid.UUID(file_id)
 
     # Now, check the metadata of the uploaded file
@@ -340,7 +342,9 @@ def test_api_documents_attachment_upload_unsafe():
     match = pattern.search(file_path)
     file_id = match.group(1)
 
+    assert "-unsafe" in file_id
     # Validate that file_id is a valid UUID
+    file_id = file_id.replace("-unsafe", "")
     uuid.UUID(file_id)
 
     # Now, check the metadata of the uploaded file