diff --git a/apps/web/supabase/migrations/20221215192558_schema.sql b/apps/web/supabase/migrations/20221215192558_schema.sql
index 90f66127d..211f0c8cf 100644
--- a/apps/web/supabase/migrations/20221215192558_schema.sql
+++ b/apps/web/supabase/migrations/20221215192558_schema.sql
@@ -1595,7 +1595,8 @@ on conflict (
         trial_ends_at = excluded.trial_ends_at
     returning
         * into new_subscription;
-    -- Upsert subscription items
+
+    -- Upsert subscription items and delete ones that are not in the line_items array
     with item_data as (
         select
             (line_item ->> 'id')::varchar as line_item_id,
@@ -1607,7 +1608,19 @@ on conflict (
             (line_item ->> 'interval')::varchar as intv,
             (line_item ->> 'interval_count')::integer as intv_count
         from
-            jsonb_array_elements(line_items) as line_item)
+            jsonb_array_elements(line_items) as line_item
+    ),
+    line_item_ids as (
+        select line_item_id from item_data
+    ),
+    deleted_items as (
+        delete from
+            public.subscription_items
+        where
+            public.subscription_items.subscription_id = new_subscription.id
+            and public.subscription_items.id not in (select line_item_id from line_item_ids)
+        returning *
+    )
     insert into public.subscription_items(
         id,
         subscription_id,
@@ -1964,6 +1977,28 @@ on conflict (
     returning
         * into new_order;
 
+    -- Upsert order items and delete ones that are not in the line_items array
+    with item_data as (
+        select
+            (line_item ->> 'id')::varchar as line_item_id,
+            (line_item ->> 'product_id')::varchar as prod_id,
+            (line_item ->> 'variant_id')::varchar as var_id,
+            (line_item ->> 'price_amount')::numeric as price_amt,
+            (line_item ->> 'quantity')::integer as qty
+        from
+            jsonb_array_elements(line_items) as line_item
+    ),
+    line_item_ids as (
+        select line_item_id from item_data
+    ),
+    deleted_items as (
+        delete from
+            public.order_items
+        where
+            public.order_items.order_id = new_order.id
+            and public.order_items.id not in (select line_item_id from line_item_ids)
+        returning *
+    )
     insert into public.order_items(
         id,
         order_id,
@@ -1972,18 +2007,18 @@ on conflict (
         price_amount,
         quantity)
     select
-        (line_item ->> 'id')::varchar,
+        line_item_id,
         target_order_id,
-(line_item ->> 'product_id')::varchar,
-(line_item ->> 'variant_id')::varchar,
-(line_item ->> 'price_amount')::numeric,
-(line_item ->> 'quantity')::integer
+        prod_id,
+        var_id,
+        price_amt,
+        qty
     from
-        jsonb_array_elements(line_items) as line_item
-on conflict (id)
-    do update set
-        price_amount = excluded.price_amount,
-        quantity = excluded.quantity;
+        item_data
+    on conflict (id)
+        do update set
+            price_amount = excluded.price_amount,
+            quantity = excluded.quantity;
 
     return new_order;
 
diff --git a/apps/web/supabase/tests/database/personal-billing-orders.test.sql b/apps/web/supabase/tests/database/personal-billing-orders.test.sql
index c7ad32bfa..f1ec6c4ba 100644
--- a/apps/web/supabase/tests/database/personal-billing-orders.test.sql
+++ b/apps/web/supabase/tests/database/personal-billing-orders.test.sql
@@ -12,7 +12,7 @@ INSERT INTO public.billing_customers(account_id, provider, customer_id)
 VALUES (tests.get_supabase_uid('primary_owner'), 'stripe', 'cus_test');
 
 -- Call the upsert_order function
-SELECT public.upsert_order(tests.get_supabase_uid('primary_owner'), 'cus_test', 'order_test', 'pending', 'stripe', 100, 'usd', '[{"id":"order_item_1", "product_id": "prod_test", "variant_id": "var_test", "price_amount": 100, "quantity": 1}]');
+SELECT public.upsert_order(tests.get_supabase_uid('primary_owner'), 'cus_test', 'order_test', 'pending', 'stripe', 100, 'usd', '[{"id":"order_item_1", "product_id": "prod_test", "variant_id": "var_test", "price_amount": 100, "quantity": 1}, {"id":"order_item_2", "product_id": "prod_test", "variant_id": "var_test_2", "price_amount": 100, "quantity": 1}]');
 
 -- Verify that the order was created correctly
 SELECT is(
@@ -24,37 +24,42 @@ SELECT is(
 -- Verify that the subscription items were created correctly
 SELECT row_eq(
     $$ select count(*) from order_items where order_id = 'order_test' $$,
-    row(1::bigint),
+    row(2::bigint),
     'The order items should be created'
 );
 
 -- Call the upsert_order function again to update the order
-SELECT public.upsert_order(tests.get_supabase_uid('primary_owner'), 'cus_test', 'order_test', 'succeeded', 'stripe', 100, 'usd', '[{"id":"order_item_1", "product_id": "prod_test", "variant_id": "var_test", "price_amount": 100, "quantity": 10}]');
+select public.upsert_order(tests.get_supabase_uid('primary_owner'), 'cus_test', 'order_test', 'succeeded', 'stripe', 100, 'usd', '[{"id":"order_item_1", "product_id": "prod_test", "variant_id": "var_test", "price_amount": 100, "quantity": 10}]');
 
 -- Verify that the order was updated correctly
-SELECT is(
-  (SELECT status FROM public.orders WHERE id = 'order_test'),
+select is(
+  (select status FROM public.orders WHERE id = 'order_test'),
   'succeeded',
   'The order status should be succeeded'
 );
 
-SELECT row_eq(
+select row_eq(
     $$ select quantity from order_items where variant_id = 'var_test' $$,
     row(10::int),
     'The subscription items should be updated'
 );
 
+select is_empty(
+  $$ select * from order_items where id = 'order_item_2' $$,
+  'The order item should be deleted when the order is updated'
+);
+
 select tests.authenticate_as('primary_owner');
 
 -- account can read their own subscription
-SELECT isnt_empty(
+select isnt_empty(
   $$ select 1 from orders where id = 'order_test' $$,
     'The account can read their own order'
 );
 
-SELECT isnt_empty(
+select isnt_empty(
   $$ select * from order_items where order_id = 'order_test' $$,
-    'The account can read their own order'
+    'The account can read their own orders items'
 );
 
 -- foreigners
@@ -62,17 +67,18 @@ select tests.create_supabase_user('foreigner');
 select tests.authenticate_as('foreigner');
 
 -- account cannot read other's subscription
-SELECT is_empty(
+select is_empty(
   $$ select 1 from orders where id = 'order_test' $$,
     'The account cannot read the other account orders'
 );
 
-SELECT is_empty(
+select is_empty(
   $$ select 1 from order_items where order_id = 'order_test' $$,
     'The account cannot read the other account order items'
 );
 
 -- Finish the tests and clean up
-SELECT * FROM finish();
-ROLLBACK;
+select * from finish();
+
+rollback;
 
diff --git a/apps/web/supabase/tests/database/personal-billing-subscriptions.test.sql b/apps/web/supabase/tests/database/personal-billing-subscriptions.test.sql
index 542cc1746..00007af91 100644
--- a/apps/web/supabase/tests/database/personal-billing-subscriptions.test.sql
+++ b/apps/web/supabase/tests/database/personal-billing-subscriptions.test.sql
@@ -33,13 +33,23 @@ SELECT public.upsert_subscription(tests.get_supabase_uid('primary_owner'), 'cus_
         "quantity": 2,
         "interval": "month",
         "interval_count": 1
+    },
+    {
+        "id": "sub_789",
+        "product_id": "prod_test_3",
+        "variant_id": "var_test_3",
+        "type": "flat",
+        "price_amount": 2000,
+        "quantity": 2,
+        "interval": "month",
+        "interval_count": 1
     }
 ]');
 
 -- Verify that the subscription items were created correctly
 SELECT row_eq(
     $$ select count(*) from subscription_items where subscription_id = 'sub_test' $$,
-    row(2::bigint),
+    row(3::bigint),
     'The subscription items should be created'
 );
 
@@ -95,24 +105,34 @@ SELECT row_eq(
 );
 
 -- Verify that the subscription was updated correctly
-SELECT is(
-  (SELECT active FROM public.subscriptions WHERE id = 'sub_test'),
+select is(
+  (select active FROM public.subscriptions WHERE id = 'sub_test'),
   false,
   'The subscription should be inactive'
 );
 
-SELECT is(
-  (SELECT status FROM public.subscriptions WHERE id = 'sub_test'),
+select is(
+  (select status FROM public.subscriptions WHERE id = 'sub_test'),
   'past_due',
   'The subscription status should be past_due'
 );
 
+select isnt_empty(
+  $$ select * from public.subscription_items where subscription_id = 'sub_test' $$,
+    'The account can read their own subscription items'
+);
+
+select is_empty(
+  $$ select * from public.subscription_items where subscription_id = 'sub_test' and variant_id = 'var_test_3' $$,
+  'The subscription items should be deleted when the subscription is updated and the item is missing'
+);
+
 -- Call the upsert_subscription function again to update the subscription
-SELECT public.upsert_subscription(tests.get_supabase_uid('primary_owner'), 'cus_test', 'sub_test', true, 'active', 'stripe', false, 'usd', now(), now() + interval '1 month', '[]');
+select public.upsert_subscription(tests.get_supabase_uid('primary_owner'), 'cus_test', 'sub_test', true, 'active', 'stripe', false, 'usd', now(), now() + interval '1 month', '[]');
 
 -- Verify that the subscription was updated correctly
-SELECT is(
-  (SELECT active FROM public.subscriptions WHERE id = 'sub_test'),
+select is(
+  (select active FROM public.subscriptions WHERE id = 'sub_test'),
   true,
   'The subscription should be active'
 );
@@ -120,14 +140,14 @@ SELECT is(
 select tests.authenticate_as('primary_owner');
 
 -- account can read their own subscription
-SELECT isnt_empty(
+select isnt_empty(
   $$ select 1 from subscriptions where id = 'sub_test' $$,
     'The account can read their own subscription'
 );
 
-SELECT isnt_empty(
+select is_empty(
   $$ select * from subscription_items where subscription_id = 'sub_test' $$,
-    'The account can read their own subscription items'
+    'No subscription items should be returned when the subscription is empty'
 );
 
 -- users cannot manually update subscriptions
diff --git a/apps/web/supabase/tests/database/team-billing-orders.test.sql b/apps/web/supabase/tests/database/team-billing-orders.test.sql
index d7c58a761..bfb578ad5 100644
--- a/apps/web/supabase/tests/database/team-billing-orders.test.sql
+++ b/apps/web/supabase/tests/database/team-billing-orders.test.sql
@@ -12,7 +12,12 @@ INSERT INTO public.billing_customers(account_id, provider, customer_id)
 VALUES (makerkit.get_account_id_by_slug('makerkit'), 'stripe', 'cus_test');
 
 -- Call the upsert_order function
-SELECT public.upsert_order(makerkit.get_account_id_by_slug('makerkit'), 'cus_test', 'order_test', 'pending', 'stripe', 100, 'usd', '[{"id":"order_item_1", "product_id": "prod_test", "variant_id": "var_test", "price_amount": 100, "quantity": 1}]');
+SELECT public.upsert_order(makerkit.get_account_id_by_slug('makerkit'), 'cus_test', 'order_test', 'pending', 'stripe', 100, 'usd', '[
+    {"id":"order_item_1", "product_id": "prod_test", "variant_id": "var_test", "price_amount": 100, "quantity": 1},
+    {"id":"order_item_2", "product_id": "prod_test", "variant_id": "var_test_2", "price_amount": 100, "quantity": 1},
+    {"id":"order_item_3", "product_id": "prod_test", "variant_id": "var_test_3", "price_amount": 100, "quantity": 1},
+    {"id":"order_item_4", "product_id": "prod_test", "variant_id": "var_test_4", "price_amount": 100, "quantity": 1}
+]');
 
 -- Verify that the order was created correctly
 SELECT is(
@@ -24,12 +29,22 @@ SELECT is(
 -- Verify that the subscription items were created correctly
 SELECT row_eq(
     $$ select count(*) from order_items where order_id = 'order_test' $$,
-    row(1::bigint),
+    row(4::bigint),
     'The order items should be created'
 );
 
 -- Call the upsert_order function again to update the order
-SELECT public.upsert_order(makerkit.get_account_id_by_slug('makerkit'), 'cus_test', 'order_test', 'succeeded', 'stripe', 100, 'usd', '[{"id":"order_item_1", "product_id": "prod_test", "variant_id": "var_test", "price_amount": 100, "quantity": 10}]');
+SELECT public.upsert_order(makerkit.get_account_id_by_slug('makerkit'), 'cus_test', 'order_test', 'succeeded', 'stripe', 100, 'usd', '[
+    {"id":"order_item_1", "product_id": "prod_test", "variant_id": "var_test", "price_amount": 100, "quantity": 10},
+    {"id":"order_item_2", "product_id": "prod_test", "variant_id": "var_test_2", "price_amount": 200, "quantity": 1}
+]');
+
+-- Verify that the subscription items were created correctly
+SELECT row_eq(
+    $$ select count(*) from order_items where order_id = 'order_test' $$,
+    row(2::bigint),
+    'The order items should be updated'
+);
 
 -- Verify that the order was updated correctly
 SELECT is(
@@ -44,6 +59,12 @@ SELECT row_eq(
     'The subscription items should be updated'
 );
 
+SELECT row_eq(
+    $$ select price_amount from order_items where variant_id = 'var_test_2' $$,
+    row(200::numeric),
+    'The subscription items should be updated'
+);
+
 select tests.authenticate_as('member');
 
 -- account can read their own subscription
diff --git a/apps/web/supabase/tests/database/team-billing-subscriptions.test.sql b/apps/web/supabase/tests/database/team-billing-subscriptions.test.sql
index 2aa6b13e7..b69e59fcf 100644
--- a/apps/web/supabase/tests/database/team-billing-subscriptions.test.sql
+++ b/apps/web/supabase/tests/database/team-billing-subscriptions.test.sql
@@ -33,13 +33,23 @@ SELECT public.upsert_subscription(makerkit.get_account_id_by_slug('makerkit'), '
         "quantity": 2,
         "interval": "month",
         "interval_count": 1
+    },
+    {
+        "id": "sub_789",
+        "product_id": "prod_test_3",
+        "variant_id": "var_test_3",
+        "type": "flat",
+        "price_amount": 2000,
+        "quantity": 2,
+        "interval": "month",
+        "interval_count": 1
     }
 ]');
 
 -- Verify that the subscription items were created correctly
 SELECT row_eq(
     $$ select count(*) from subscription_items where subscription_id = 'sub_test' $$,
-    row(2::bigint),
+    row(3::bigint),
     'The subscription items should be created'
 );
 
@@ -80,6 +90,12 @@ SELECT public.upsert_subscription(makerkit.get_account_id_by_slug('makerkit'), '
     }
 ]');
 
+SELECT row_eq(
+    $$ select count(*) from subscription_items where subscription_id = 'sub_test' $$,
+    row(2::bigint),
+    'The subscription items should be updated'
+);
+
 -- Verify that the subscription items were updated correctly
 SELECT row_eq(
     $$ select price_amount from subscription_items where variant_id = 'var_test' $$,
@@ -107,6 +123,16 @@ SELECT is(
   'The subscription status should be past_due'
 );
 
+select tests.authenticate_as('member');
+
+SELECT row_eq(
+    $$ select count(*) from subscription_items where subscription_id = 'sub_test' $$,
+    row(2::bigint),
+    'The member can also read the subscription items'
+);
+
+set role service_role;
+
 -- Call the upsert_subscription function again to update the subscription
 SELECT public.upsert_subscription(tests.get_supabase_uid('primary_owner'), 'cus_test', 'sub_test', true, 'active', 'stripe', false, 'usd', now(), now() + interval '1 month', '[]');
 
@@ -125,9 +151,9 @@ select isnt_empty(
     'The account can read their own subscription'
 );
 
-select isnt_empty(
+select is_empty(
   $$ select * from subscription_items where subscription_id = 'sub_test' $$,
-    'The account can read their own subscription items'
+    'The subscription items are now empty'
 );
 
 select is(