diff --git a/litellm/proxy/utils.py b/litellm/proxy/utils.py
index a7f327c2e59..ec0b46990cb 100644
--- a/litellm/proxy/utils.py
+++ b/litellm/proxy/utils.py
@@ -5559,6 +5559,16 @@ _LOCK_TEAMS_BY_ID_SQL: Final = (
 )
 
 
+def _user_unique_conflict_message(metadata: object, user_id: object) -> str:
+    match metadata:
+        case {"target": ["user_id"]}:
+            return f"User with id {user_id} already exists"
+        case {"target": ["sso_user_id"]}:
+            return "User with this sso_user_id already exists"
+        case _:
+            return "User conflicts with an existing unique value"
+
+
 class PrismaClient:
     spend_log_transactions: list = []
     _spend_log_transactions_lock = asyncio.Lock()
@@ -6446,6 +6456,7 @@ class PrismaClient:
         max_tries=3,  # maximum number of retries
         max_time=10,  # maximum total time to retry for
         on_backoff=on_backoff,  # specifying the function to call on backoff
+        giveup=lambda exc: isinstance(exc, HTTPException) and exc.status_code == 409,
     )
     @log_db_metrics
     async def insert_data(
@@ -6504,7 +6515,7 @@ class PrismaClient:
                 except UniqueViolationError as e:
                     raise HTTPException(
                         status_code=409,
-                        detail={"error": f"User with id {db_data['user_id']} already exists"},
+                        detail={"error": _user_unique_conflict_message(e.meta, db_data["user_id"])},
                     ) from e
                 except Exception as e:
                     if (
diff --git a/tests/unit/proxy/management_endpoints/test_internal_user_endpoints.py b/tests/unit/proxy/management_endpoints/test_internal_user_endpoints.py
index a7c9703e693..b96a5b606eb 100644
--- a/tests/unit/proxy/management_endpoints/test_internal_user_endpoints.py
+++ b/tests/unit/proxy/management_endpoints/test_internal_user_endpoints.py
@@ -73,7 +73,10 @@ async def test_new_user_returns_conflict_when_id_is_taken_after_duplicate_check(
     table: Final = SimpleNamespace(
         find_first=AsyncMock(return_value=None),
         count=AsyncMock(return_value=0),
-        create=AsyncMock(side_effect=UniqueViolationError({}, message="Unique constraint failed on user_id")),
+        create=AsyncMock(side_effect=UniqueViolationError(
+            {"user_facing_error": {"meta": {"target": ["user_id"]}}},
+            message="Unique constraint failed on user_id",
+        )),
         upsert=AsyncMock(return_value=LiteLLM_UserTable(user_id="employee-42")),
     )
     mocker.patch("prisma.Prisma", return_value=SimpleNamespace(litellm_usertable=table))
diff --git a/tests/unit/proxy/utils/prisma_and_spend/test_prisma_client_writes.py b/tests/unit/proxy/utils/prisma_and_spend/test_prisma_client_writes.py
index e335b08f040..a9950a9d8e3 100644
--- a/tests/unit/proxy/utils/prisma_and_spend/test_prisma_client_writes.py
+++ b/tests/unit/proxy/utils/prisma_and_spend/test_prisma_client_writes.py
@@ -18,8 +18,10 @@ from types import SimpleNamespace
 from typing import Final
 from unittest.mock import AsyncMock, MagicMock, patch
 
+import httpx
 import pytest
 from fastapi import HTTPException
+from prisma.errors import UniqueViolationError
 
 from litellm._service_logger import ServiceTypes
 from litellm.models.user import LiteLLM_UserTable
@@ -192,6 +194,48 @@ async def test_insert_data_team_serializes_members(prisma_client: PrismaClient)
     assert create_payload["team_id"] == "t1"
 
 
+@pytest.mark.asyncio
+@pytest.mark.parametrize(
+    ("metadata", "message"),
+    [
+        ({"target": ["user_id"]}, "User with id requested-user already exists"),
+        ({"target": ["sso_user_id"]}, "User with this sso_user_id already exists"),
+        (None, "User conflicts with an existing unique value"),
+        ({"target": ["unknown_field"]}, "User conflicts with an existing unique value"),
+    ],
+)
+async def test_user_conflict_names_constraint_and_does_not_retry(
+    prisma_client: PrismaClient,
+    metadata: Mapping[str, object] | None,
+    message: str,
+) -> None:
+    create: Final = AsyncMock(side_effect=UniqueViolationError({"user_facing_error": {"meta": metadata}}))
+    prisma_client.db.litellm_usertable.create = create
+    with pytest.raises(HTTPException) as error:
+        await prisma_client.insert_data(
+            data={"user_id": "requested-user", "sso_user_id": "sso-subject"},
+            table_name="user", allow_existing_user=False,
+        )
+    assert error.value.status_code == 409
+    assert error.value.detail == {"error": message}
+    assert create.await_count == 1
+
+
+@pytest.mark.asyncio
+async def test_user_insert_still_retries_transient_connection_failure(
+    prisma_client: PrismaClient, monkeypatch: pytest.MonkeyPatch
+) -> None:
+    row: Final = LiteLLM_UserTable(user_id="requested-user")
+    create: Final = AsyncMock(side_effect=[httpx.ConnectError("connection unavailable"), row])
+    prisma_client.db.litellm_usertable.create = create
+    monkeypatch.setattr("asyncio.sleep", AsyncMock())
+    result: Final = await prisma_client.insert_data(
+        data={"user_id": row.user_id}, table_name="user", allow_existing_user=False
+    )
+    assert result is row
+    assert create.await_count == 2
+
+
 @pytest.mark.asyncio
 async def test_insert_data_user_organization_fk_raises_400(
     prisma_client: PrismaClient,