diff --git a/accounts/api/serializers.py b/accounts/api/serializers.py
index 7ed4d78..50b426f 100644
--- a/accounts/api/serializers.py
+++ b/accounts/api/serializers.py
@@ -196,21 +196,25 @@ class ProfileSerializer(serializers.ModelSerializer):
             "grace_period_end_date": None,
         }
         today = timezone.now().date()
-        active_subscriptions = PrincipalSubscription.objects.filter(
+
+        # Attempt to find the active subscription with the furthest grace_period_end_date
+        latest_subscription = PrincipalSubscription.objects.filter(
             principal=obj,
             is_paid=True,
             cancelled=False,
             deleted=False,
             active=True,
             status=SubscriptionStatus.ACTIVE,
-            end_date__gte=today,
-        )
-        if active_subscriptions.exists():
-            latest_subscription = active_subscriptions.last()
-            subscription_status["has_active_subscription"] = latest_subscription.is_paid and latest_subscription.status == SubscriptionStatus.ACTIVE and latest_subscription.end_date >= today
-            subscription_status["in_grace_period"] = not subscription_status["has_active_subscription"] and latest_subscription.grace_period_end_date >= today
-            subscription_status["grace_period_end_date"] = latest_subscription.grace_period_end_date if subscription_status["in_grace_period"] else None
-        return active_subscriptions.exists()
+        ).order_by('-grace_period_end_date').first()  # Order by descending grace_period_end_date and take the first
+
+        if latest_subscription:
+            # Check if we're within the grace period
+            if today <= latest_subscription.grace_period_end_date:
+                subscription_status['has_active_subscription'] = today <= latest_subscription.end_date
+                subscription_status['in_grace_period'] = latest_subscription.end_date < today <= latest_subscription.grace_period_end_date
+                subscription_status['grace_period_end_date'] = latest_subscription.grace_period_end_date
+
+        return subscription_status
 
     def to_representation(self, instance):
         data = super().to_representation(instance)