diff --git a/hindsight-api/alembic/versions/d9f6a3b4c5e2_rename_bank_to_interactions.py b/hindsight-api/alembic/versions/d9f6a3b4c5e2_rename_bank_to_interactions.py
index 79e0422e..82d2835c 100644
--- a/hindsight-api/alembic/versions/d9f6a3b4c5e2_rename_bank_to_interactions.py
+++ b/hindsight-api/alembic/versions/d9f6a3b4c5e2_rename_bank_to_interactions.py
@@ -17,12 +17,12 @@ depends_on = None
 
 
 def upgrade():
+    # Drop old check constraint FIRST (before updating data)
+    op.drop_constraint('memory_units_fact_type_check', 'memory_units', type_='check')
+
     # Update existing 'bank' values to 'interactions'
     op.execute("UPDATE memory_units SET fact_type = 'interactions' WHERE fact_type = 'bank'")
 
-    # Drop old check constraint
-    op.drop_constraint('memory_units_fact_type_check', 'memory_units', type_='check')
-
     # Create new check constraint with 'interactions' instead of 'bank'
     op.create_check_constraint(
         'memory_units_fact_type_check',
@@ -32,12 +32,12 @@ def upgrade():
 
 
 def downgrade():
+    # Drop new check constraint FIRST
+    op.drop_constraint('memory_units_fact_type_check', 'memory_units', type_='check')
+
     # Update 'interactions' back to 'bank'
     op.execute("UPDATE memory_units SET fact_type = 'bank' WHERE fact_type = 'interactions'")
 
-    # Drop new check constraint
-    op.drop_constraint('memory_units_fact_type_check', 'memory_units', type_='check')
-
     # Recreate old check constraint
     op.create_check_constraint(
         'memory_units_fact_type_check',