diff --git a/lms/services/upsert.py b/lms/services/upsert.py
index 8db15925e6..c02754e229 100644
--- a/lms/services/upsert.py
+++ b/lms/services/upsert.py
@@ -10,7 +10,7 @@ def bulk_upsert(
     model_class,
     values: list[dict],
     index_elements: list[str],
-    update_columns: list[str],
+    update_columns: list[str | tuple],
 ):
     """
     Create or update the specified values in a table.
@@ -50,7 +50,16 @@ def bulk_upsert(
         # The columns to use to find matching rows.
         index_elements=index_elements,
         # The columns to update.
-        set_={element: getattr(base.excluded, element) for element in update_columns},
+        set_={
+            # For tuples include the two elements as the key and value of the dict
+            # For strings use value: excluded.value by default
+            (element[0] if isinstance(element, tuple) else element): (
+                element[1]
+                if isinstance(element, tuple)
+                else getattr(base.excluded, element)
+            )
+            for element in update_columns
+        },
     ).returning(*index_elements_columns)
 
     result = db.execute(stmt)
diff --git a/lms/services/user.py b/lms/services/user.py
index 53e57dd632..6a7dbca286 100644
--- a/lms/services/user.py
+++ b/lms/services/user.py
@@ -1,6 +1,6 @@
 from functools import lru_cache
 
-from sqlalchemy import select
+from sqlalchemy import func, select, text
 from sqlalchemy.exc import NoResultFound
 from sqlalchemy.sql import Select
 
@@ -89,7 +89,18 @@ def upsert_lms_user(self, user: User, lti_params: LTIParams) -> LMSUser:
                 }
             ],
             index_elements=["h_userid"],
-            update_columns=["updated", "display_name", "email", "lti_v13_user_id"],
+            update_columns=[
+                "updated",
+                "display_name",
+                "email",
+                (
+                    "lti_v13_user_id",
+                    func.coalesce(
+                        text('"excluded"."lti_v13_user_id"'),
+                        text('"lms_user"."lti_v13_user_id"'),
+                    ),
+                ),
+            ],
         ).one()
         bulk_upsert(
             self._db,