diff --git a/corporate/views/portico.py b/corporate/views/portico.py
index 0cbf13e5b9..4af8baac32 100644
--- a/corporate/views/portico.py
+++ b/corporate/views/portico.py
@@ -74,6 +74,8 @@ class PlansPageContext:
     is_new_customer: bool = False
     on_free_tier: bool = False
     customer_plan: Optional[CustomerPlan] = None
+    is_legacy_server_with_scheduled_upgrade: bool = False
+    legacy_server_new_plan: Optional[CustomerPlan] = None
 
     billing_base_url: str = ""
 
@@ -183,6 +185,16 @@ def remote_server_plans_page(
                 CustomerPlan.TIER_SELF_HOSTED_BASE,
             )
             context.on_free_trial = is_customer_on_free_trial(context.customer_plan)
+            context.is_legacy_server_with_scheduled_upgrade = (
+                context.customer_plan.status == CustomerPlan.SWITCH_PLAN_TIER_AT_PLAN_END
+            )
+            if context.is_legacy_server_with_scheduled_upgrade:
+                assert context.customer_plan.end_date is not None
+                context.legacy_server_new_plan = CustomerPlan.objects.get(
+                    customer=customer,
+                    billing_cycle_anchor=context.customer_plan.end_date,
+                    status=CustomerPlan.NEVER_STARTED,
+                )
 
     context.is_new_customer = (
         not context.on_free_tier and context.customer_plan is None and not context.is_sponsored
diff --git a/templates/corporate/pricing_model.html b/templates/corporate/pricing_model.html
index 86de684bfc..1078f7d490 100644
--- a/templates/corporate/pricing_model.html
+++ b/templates/corporate/pricing_model.html
@@ -188,7 +188,11 @@
                         </div>
                         <div class="bottom">
                             <div class="text-content">
-                                {% if is_self_hosted_realm and on_free_tier and not sponsorship_pending %}
+                                {% if is_legacy_server_with_scheduled_upgrade and legacy_server_new_plan.tier == legacy_server_new_plan.TIER_SELF_HOSTED_BUSINESS %}
+                                <a href="{{ billing_base_url }}/billing/" class="button current-plan-button">
+                                    Upgrade is scheduled
+                                </a>
+                                {% elif is_self_hosted_realm and on_free_tier and not sponsorship_pending %}
                                 <a href="{{ billing_base_url }}/sponsorship/" class="button current-plan-button request-sponsorship">
                                     Request sponsorship
                                 </a>
@@ -247,7 +251,11 @@
                         </div>
                         <div class="bottom">
                             <div class="text-content">
-                                {% if is_self_hosted_realm and customer_plan and customer_plan.tier == customer_plan.TIER_SELF_HOSTED_ENTERPRISE %}
+                                {% if is_legacy_server_with_scheduled_upgrade and legacy_server_new_plan.tier == legacy_server_new_plan.TIER_SELF_HOSTED_ENTERPRISE %}
+                                <a href="{{ billing_base_url }}/billing/" class="button current-plan-button">
+                                    Upgrade is scheduled
+                                </a>
+                                {% elif is_self_hosted_realm and customer_plan and customer_plan.tier == customer_plan.TIER_SELF_HOSTED_ENTERPRISE %}
                                 <a href='{{ billing_base_url }}/billing' class="button current-plan-button" type="button">
                                     <i class="icon current-plan-icon"></i>
                                     Current plan