diff --git a/corporate/lib/stripe.py b/corporate/lib/stripe.py
index 46c61a99c2..2438213158 100644
--- a/corporate/lib/stripe.py
+++ b/corporate/lib/stripe.py
@@ -579,6 +579,7 @@ class SupportType(Enum):
     update_required_plan_tier = 8
     configure_fixed_price_plan = 9
     delete_fixed_price_next_plan = 10
+    configure_temporary_courtesy_plan = 11
 
 
 class SupportViewRequest(TypedDict, total=False):
@@ -1411,6 +1412,28 @@ class BillingSession(ABC):
             plan_tier_name = CustomerPlan.name_from_tier(new_plan_tier)
         return f"Required plan tier for {self.billing_entity_display_name} set to {plan_tier_name}."
 
+    def configure_temporary_courtesy_plan(self, end_date_string: str) -> str:
+        plan_end_date = datetime.strptime(end_date_string, "%Y-%m-%d").replace(tzinfo=timezone.utc)
+        if plan_end_date.date() <= timezone_now().date():
+            raise SupportRequestError(
+                f"Cannot configure a courtesy plan for {self.billing_entity_display_name} to end on {end_date_string}."
+            )
+        customer = self.get_customer()
+        if customer is not None:
+            plan = get_current_plan_by_customer(customer)
+            if plan is not None:
+                raise SupportRequestError(
+                    f"Cannot configure a courtesy plan for {self.billing_entity_display_name} because of current plan."
+                )
+        plan_anchor_date = timezone_now()
+        if isinstance(self, RealmBillingSession):
+            raise SupportRequestError(
+                f"Cannot currently configure a courtesy plan for {self.billing_entity_display_name}."
+            )  # nocoverage
+
+        self.migrate_customer_to_legacy_plan(plan_anchor_date, plan_end_date)
+        return f"Temporary courtesy plan for {self.billing_entity_display_name} configured to end on {end_date_string}."
+
     def configure_fixed_price_plan(self, fixed_price: int, sent_invoice_id: str | None) -> str:
         customer = self.get_customer()
         if customer is None:
@@ -3384,6 +3407,10 @@ class BillingSession(ABC):
             new_fixed_price = support_request["fixed_price"]
             sent_invoice_id = support_request["sent_invoice_id"]
             success_message = self.configure_fixed_price_plan(new_fixed_price, sent_invoice_id)
+        elif support_type == SupportType.configure_temporary_courtesy_plan:
+            assert support_request["plan_end_date"] is not None
+            temporary_plan_end_date = support_request["plan_end_date"]
+            success_message = self.configure_temporary_courtesy_plan(temporary_plan_end_date)
         elif support_type == SupportType.update_billing_modality:
             assert support_request["billing_modality"] is not None
             assert support_request["billing_modality"] in VALID_BILLING_MODALITY_VALUES
diff --git a/corporate/tests/test_stripe.py b/corporate/tests/test_stripe.py
index a76dfd07fc..7840aec9b8 100644
--- a/corporate/tests/test_stripe.py
+++ b/corporate/tests/test_stripe.py
@@ -7352,7 +7352,9 @@ class TestRemoteRealmBillingFlow(StripeTestCase, RemoteRealmBillingTestCase):
         self.assertEqual(success_message, "Fixed price offer deleted")
         result = self.client_get("/activity/remote/support", {"q": "example.com"})
         self.assert_not_in_success_response(["Next plan information:"], result)
-        self.assert_in_success_response(["Fixed price", "Annual amount in dollars"], result)
+        self.assert_in_success_response(
+            ["Configure fixed price plan", "Annual amount in dollars"], result
+        )
 
     @responses.activate
     @mock_stripe()
diff --git a/corporate/tests/test_support_views.py b/corporate/tests/test_support_views.py
index aef416e207..37752f8793 100644
--- a/corporate/tests/test_support_views.py
+++ b/corporate/tests/test_support_views.py
@@ -503,6 +503,50 @@ class TestRemoteServerSupportEndpoint(ZulipTestCase):
             ["Cannot update current plan for realm-name-5 to end on 2020-01-01."], result
         )
 
+    def test_configure_temporary_courtesy_plan(self) -> None:
+        iago = self.example_user("iago")
+        self.login_user(iago)
+        remote_realm = RemoteRealm.objects.get(name="realm-name-4")
+        # Cannot configure courtesy plan to end in the past.
+        result = self.client_post(
+            "/activity/remote/support",
+            {
+                "remote_realm_id": f"{remote_realm.id}",
+                "temporary_courtesy_plan": "2010-03-01",
+            },
+        )
+        self.assert_in_success_response(
+            ["Cannot configure a courtesy plan for realm-name-4 to end on 2010-03-01."],
+            result,
+        )
+        # Cannot configure courtesy plan if there is a current plan for billing entity.
+        result = self.client_post(
+            "/activity/remote/support",
+            {
+                "remote_realm_id": f"{remote_realm.id}",
+                "temporary_courtesy_plan": "2050-03-01",
+            },
+        )
+        self.assert_in_success_response(
+            ["Cannot configure a courtesy plan for realm-name-4 because of current plan."],
+            result,
+        )
+        remote_realm = RemoteRealm.objects.get(name="realm-name-2")
+        assert remote_realm.plan_type == RemoteRealm.PLAN_TYPE_SELF_MANAGED
+        result = self.client_post(
+            "/activity/remote/support",
+            {
+                "remote_realm_id": f"{remote_realm.id}",
+                "temporary_courtesy_plan": "2050-03-01",
+            },
+        )
+        self.assert_in_success_response(
+            ["Temporary courtesy plan for realm-name-2 configured to end on 2050-03-01."],
+            result,
+        )
+        remote_realm.refresh_from_db()
+        assert remote_realm.plan_type == RemoteRealm.PLAN_TYPE_SELF_MANAGED_LEGACY
+
     def test_discount_support_actions_when_upgrade_scheduled(self) -> None:
         remote_realm = RemoteRealm.objects.get(name="realm-name-4")
         billing_session = RemoteRealmBillingSession(remote_realm=remote_realm)
diff --git a/corporate/views/support.py b/corporate/views/support.py
index 15745e68eb..e8af7dea7d 100644
--- a/corporate/views/support.py
+++ b/corporate/views/support.py
@@ -651,6 +651,10 @@ def remote_servers_support(
     modify_plan: VALID_MODIFY_PLAN_METHODS | None = None,
     delete_fixed_price_next_plan: Json[bool] = False,
     remote_server_status: VALID_STATUS_VALUES | None = None,
+    temporary_courtesy_plan: Annotated[
+        str, AfterValidator(lambda x: check_date("temporary_courtesy_plan", x))
+    ]
+    | None = None,
 ) -> HttpResponse:
     context: dict[str, Any] = {}
 
@@ -706,6 +710,11 @@ def remote_servers_support(
                 fixed_price=fixed_price,
                 sent_invoice_id=sent_invoice_id,
             )
+        elif temporary_courtesy_plan is not None:
+            support_view_request = SupportViewRequest(
+                support_type=SupportType.configure_temporary_courtesy_plan,
+                plan_end_date=temporary_courtesy_plan,
+            )
         elif billing_modality is not None:
             support_view_request = SupportViewRequest(
                 support_type=SupportType.update_billing_modality,
diff --git a/templates/corporate/support/next_plan_forms_support.html b/templates/corporate/support/next_plan_forms_support.html
index 8c28b48cfd..4efbaef627 100644
--- a/templates/corporate/support/next_plan_forms_support.html
+++ b/templates/corporate/support/next_plan_forms_support.html
@@ -1,14 +1,24 @@
-<p class="support-section-header">⏱️ Schedule fixed price plan:</p>
+<p class="support-section-header">⏱️ Schedule plan:</p>
 <form method="POST" class="remote-form">
-    <b>Fixed price</b><br />
-    {% if not is_current_plan_billable %}
+    <b>Configure fixed price plan:</b><br />
+    {% if not plan_data.is_current_plan_billable %}
     <i>Enter Invoice ID only if the customer chose to pay by invoice.</i><br />
     {% endif %}
     {{ csrf_input }}
     <input type="hidden" name="{{ remote_type }}" value="{{ remote_id }}" />
     <input type="number" name="fixed_price" placeholder="Annual amount in dollars" required />
-    {% if not is_current_plan_billable %}
+    {% if not plan_data.is_current_plan_billable %}
     <input type="text" name="sent_invoice_id" placeholder="Sent invoice ID" />
     {% endif %}
     <button type="submit" class="support-submit-button">Schedule</button>
 </form>
+{% if not plan_data.current_plan %}
+<form method="POST" class="remote-form">
+    <b>Configure temporary courtesy plan:</b><br />
+    <i>Once created, the end date for the temporary courtesy plan can be extended.</i><br />
+    {{ csrf_input }}
+    <input type="hidden" name="{{ remote_type }}" value="{{ remote_id }}" />
+    <input type="date" name="temporary_courtesy_plan" required />
+    <button type="submit" class="support-submit-button">Create</button>
+</form>
+{% endif %}
diff --git a/templates/corporate/support/remote_realm_details.html b/templates/corporate/support/remote_realm_details.html
index 96219c83bf..ca1b5b7503 100644
--- a/templates/corporate/support/remote_realm_details.html
+++ b/templates/corporate/support/remote_realm_details.html
@@ -94,7 +94,7 @@
     {% elif not remote_server_deactivated %}
     <div class="next-plan-container">
         {% with %}
-            {% set is_current_plan_billable = support_data[remote_realm.id].plan_data.is_current_plan_billable %}
+            {% set plan_data = support_data[remote_realm.id].plan_data %}
             {% set remote_id = remote_realm.id %}
             {% set remote_type = "remote_realm_id" %}
             {% include 'corporate/support/next_plan_forms_support.html' %}
diff --git a/templates/corporate/support/remote_server_support.html b/templates/corporate/support/remote_server_support.html
index 3bcf39603f..af817af4b4 100644
--- a/templates/corporate/support/remote_server_support.html
+++ b/templates/corporate/support/remote_server_support.html
@@ -139,7 +139,7 @@
                 {% elif not remote_server.deactivated %}
                 <div class="next-plan-container">
                     {% with %}
-                        {% set is_current_plan_billable = remote_servers_support_data[remote_server.id].plan_data.is_current_plan_billable %}
+                        {% set plan_data = remote_servers_support_data[remote_server.id].plan_data %}
                         {% set remote_id = remote_server.id %}
                         {% set remote_type = "remote_server_id" %}
                         {% include 'corporate/support/next_plan_forms_support.html' %}