diff --git a/corporate/lib/stripe.py b/corporate/lib/stripe.py
index af87512ca0..09be7b36d6 100644
--- a/corporate/lib/stripe.py
+++ b/corporate/lib/stripe.py
@@ -4932,8 +4932,11 @@ def invoice_plans_as_needed(event_time: Optional[datetime] = None) -> None:
                 plan.reminder_to_review_plan_email_sent = True
                 plan.save(update_fields=["reminder_to_review_plan_email_sent"])
 
+            free_plan_with_no_next_plan = not plan.is_paid() and plan.status == CustomerPlan.ACTIVE
             last_audit_log_update = remote_server.last_audit_log_update
-            if last_audit_log_update is None or plan.next_invoice_date > last_audit_log_update:
+            if not free_plan_with_no_next_plan and (
+                last_audit_log_update is None or plan.next_invoice_date > last_audit_log_update
+            ):
                 if (
                     last_audit_log_update is None
                     or plan.next_invoice_date - last_audit_log_update >= timedelta(days=1)
diff --git a/corporate/tests/test_stripe.py b/corporate/tests/test_stripe.py
index 8f75f456e2..0bf9c42e43 100644
--- a/corporate/tests/test_stripe.py
+++ b/corporate/tests/test_stripe.py
@@ -9079,11 +9079,14 @@ class TestRemoteServerBillingFlow(StripeTestCase, RemoteServerTestCase):
             self.remote_server.plan_type, RemoteZulipServer.PLAN_TYPE_SELF_MANAGED_LEGACY
         )
 
-        with mock.patch("stripe.Invoice.create") as invoice_create, time_machine.travel(
-            plan_end_date, tick=False
-        ):
-            send_server_data_to_push_bouncer(consider_usage_statistics=False)
+        with mock.patch("stripe.Invoice.create") as invoice_create, mock.patch(
+            "corporate.lib.stripe.send_email"
+        ) as send_email, time_machine.travel(plan_end_date, tick=False):
             invoice_plans_as_needed()
+            # Verify that for legacy plan with no next plan scheduled,
+            # invoice overdue email is not sent even if the last audit log
+            # update was 3 months ago.
+            send_email.assert_not_called()
             # The legacy plan is downgraded, no invoice created.
             invoice_create.assert_not_called()
 
@@ -9143,6 +9146,15 @@ class TestRemoteServerBillingFlow(StripeTestCase, RemoteServerTestCase):
         )
         licenses = max(min_licenses, server_user_count)
 
+        with mock.patch("stripe.Invoice.create") as invoice_create, mock.patch(
+            "corporate.lib.stripe.send_email"
+        ) as send_email, time_machine.travel(end_date, tick=False):
+            invoice_plans_as_needed()
+            # Verify that for legacy plan with next plan scheduled, invoice
+            # overdue email is sent if the last audit log is stale.
+            send_email.assert_called()
+            invoice_create.assert_not_called()
+
         with time_machine.travel(end_date, tick=False):
             send_server_data_to_push_bouncer(consider_usage_statistics=False)
             invoice_plans_as_needed()