diff --git a/alembic/versions/211ab850ef3d_add_sync_operations_table.py b/alembic/versions/211ab850ef3d_add_sync_operations_table.py
index 9c6e81f12..976439a32 100644
--- a/alembic/versions/211ab850ef3d_add_sync_operations_table.py
+++ b/alembic/versions/211ab850ef3d_add_sync_operations_table.py
@@ -36,7 +36,8 @@ def upgrade() -> None:
                 "FAILED",
                 "CANCELLED",
                 name="syncstatus",
-                create_type=False,
+                create_type=True,
+                checkfirst=True,
             )
         else:
             syncstatus = sa.Enum(
@@ -46,7 +47,8 @@ def upgrade() -> None:
                 "FAILED",
                 "CANCELLED",
                 name="syncstatus",
-                create_type=False,
+                create_type=True,
+                checkfirst=True,
             )
 
         # Table doesn't exist, create it normally
diff --git a/alembic/versions/c946955da633_multi_tenant_support.py b/alembic/versions/c946955da633_multi_tenant_support.py
index 3f7bde5a2..6d21f8fc7 100644
--- a/alembic/versions/c946955da633_multi_tenant_support.py
+++ b/alembic/versions/c946955da633_multi_tenant_support.py
@@ -20,6 +20,10 @@ branch_labels: Union[str, Sequence[str], None] = None
 depends_on: Union[str, Sequence[str], None] = None
 
 
+def _now():
+    return datetime.now(timezone.utc)
+
+
 def _define_user_table() -> sa.Table:
     table = sa.Table(
         "users",
@@ -76,27 +80,29 @@ def upgrade() -> None:
     user = _define_user_table()
 
     if "user_tenants" not in insp.get_table_names():
-        tenant_id_from_user = sa.select(user.c.tenant_id).scalar_subquery()
         # Define table with all necessary columns including primary key
         user_tenants = op.create_table(
             "user_tenants",
             sa.Column("user_id", sa.UUID, sa.ForeignKey("users.id"), primary_key=True),
             sa.Column("tenant_id", sa.UUID, sa.ForeignKey("tenants.id"), primary_key=True),
-            sa.Column("created_at", sa.DateTime(), default=lambda: datetime.now(timezone.utc)),
+            sa.Column(
+                "created_at", sa.DateTime(timezone=True), default=lambda: datetime.now(timezone.utc)
+            ),
         )
-        if op.get_context().dialect.name == "sqlite":
-            # If column doesn't exist create new original_extension column and update from values of extension column
-            with op.batch_alter_table("user_tenants") as batch_op:
-                batch_op.execute(
-                    user_tenants.update().values(
-                        tenant_id=tenant_id_from_user,
-                        user_id=user.c.id,
-                    )
-                )
-        else:
-            conn = op.get_bind()
-            conn.execute(
-                user_tenants.update().values(tenant_id=tenant_id_from_user, user_id=user.c.id)
+
+        # Get all users with their tenant_id
+        user_data = conn.execute(
+            sa.select(user.c.id, user.c.tenant_id).where(user.c.tenant_id.isnot(None))
+        ).fetchall()
+
+        # Insert into user_tenants table
+        if user_data:
+            op.bulk_insert(
+                user_tenants,
+                [
+                    {"user_id": user_id, "tenant_id": tenant_id, "created_at": _now()}
+                    for user_id, tenant_id in user_data
+                ],
             )
 
     tenant_id_column = _get_column(insp, "datasets", "tenant_id")
@@ -125,6 +131,6 @@ def upgrade() -> None:
 
 def downgrade() -> None:
     # ### commands auto generated by Alembic - please adjust! ###
-
+    op.drop_table("user_tenants")
     op.drop_column("datasets", "tenant_id")
     # ### end Alembic commands ###