diff --git a/corporate/lib/stripe.py b/corporate/lib/stripe.py
index bc97f5beb1..f246575309 100644
--- a/corporate/lib/stripe.py
+++ b/corporate/lib/stripe.py
@@ -1444,7 +1444,12 @@ class BillingSession(ABC):
                 assert plan.status == CustomerPlan.ACTIVE
                 old_end_date = plan.end_date
                 plan.end_date = new_end_date
-                plan.save(update_fields=["end_date"])
+                old_next_invoice_date = plan.next_invoice_date
+                # Legacy plans should be invoiced once on the end_date to
+                # downgrade or switch to a new tier.
+                if plan.tier == CustomerPlan.TIER_SELF_HOSTED_LEGACY:
+                    plan.next_invoice_date = new_end_date
+                plan.save(update_fields=["end_date", "next_invoice_date"])
                 self.write_to_audit_log(
                     event_type=AuditLogEventType.CUSTOMER_PLAN_PROPERTY_CHANGED,
                     event_time=timezone_now(),
@@ -1455,6 +1460,17 @@ class BillingSession(ABC):
                         "property": "end_date",
                     },
                 )
+                if old_next_invoice_date != plan.next_invoice_date:
+                    self.write_to_audit_log(
+                        event_type=AuditLogEventType.CUSTOMER_PLAN_PROPERTY_CHANGED,
+                        event_time=timezone_now(),
+                        extra_data={
+                            "old_value": old_next_invoice_date,
+                            "new_value": new_end_date,
+                            "plan_id": plan.id,
+                            "property": "next_invoice_date",
+                        },
+                    )
                 return f"Current plan for {self.billing_entity_display_name} updated to end on {end_date_string}."
         raise SupportRequestError(
             f"No current plan for {self.billing_entity_display_name}."
diff --git a/corporate/tests/test_support_views.py b/corporate/tests/test_support_views.py
index fc8bf8a4f0..cddade7997 100644
--- a/corporate/tests/test_support_views.py
+++ b/corporate/tests/test_support_views.py
@@ -353,6 +353,7 @@ class TestRemoteServerSupportEndpoint(ZulipTestCase):
         assert plan is not None
         self.assertEqual(plan.status, CustomerPlan.ACTIVE)
         self.assertEqual(plan.end_date, datetime(2050, 2, 1, tzinfo=timezone.utc))
+        self.assertEqual(plan.next_invoice_date, datetime(2050, 2, 1, tzinfo=timezone.utc))
 
         cordelia = self.example_user("cordelia")
         self.login_user(cordelia)
@@ -375,17 +376,22 @@ class TestRemoteServerSupportEndpoint(ZulipTestCase):
         )
         plan.refresh_from_db()
         self.assertEqual(plan.end_date, datetime(2040, 1, 1, tzinfo=timezone.utc))
-        audit_log = RemoteRealmAuditLog.objects.filter(
+        self.assertEqual(plan.next_invoice_date, datetime(2040, 1, 1, tzinfo=timezone.utc))
+        audit_logs = RemoteRealmAuditLog.objects.filter(
             event_type=RemoteRealmAuditLog.CUSTOMER_PLAN_PROPERTY_CHANGED
-        ).last()
-        assert audit_log is not None
+        ).order_by("-id")
+        assert audit_logs.exists()
+        next_invoice_date_changed_audit_log = audit_logs[0]
+        end_date_changed_audit_log = audit_logs[1]
         expected_extra_data = {
             "old_value": "2050-02-01T00:00:00Z",
             "new_value": "2040-01-01T00:00:00Z",
             "property": "end_date",
             "plan_id": plan.id,
         }
-        self.assertEqual(audit_log.extra_data, expected_extra_data)
+        self.assertEqual(end_date_changed_audit_log.extra_data, expected_extra_data)
+        expected_extra_data["property"] = "next_invoice_date"
+        self.assertEqual(next_invoice_date_changed_audit_log.extra_data, expected_extra_data)
 
         result = self.client_post(
             "/activity/remote/support",