diff --git a/src/Billing/Jobs/SubscriptionCancellationJob.cs b/src/Billing/Jobs/SubscriptionCancellationJob.cs
index c46581272e..b59bb10eaf 100644
--- a/src/Billing/Jobs/SubscriptionCancellationJob.cs
+++ b/src/Billing/Jobs/SubscriptionCancellationJob.cs
@@ -23,9 +23,9 @@ public class SubscriptionCancellationJob(
         }
 
         var subscription = await stripeFacade.GetSubscription(subscriptionId);
-        if (subscription?.Status != "unpaid")
+        if (subscription?.Status != "unpaid" ||
+            subscription.LatestInvoice?.BillingReason is not ("subscription_cycle" or "subscription_create"))
         {
-            // Subscription is no longer unpaid, skip cancellation
             return;
         }
 
diff --git a/src/Billing/Services/Implementations/SubscriptionUpdatedHandler.cs b/src/Billing/Services/Implementations/SubscriptionUpdatedHandler.cs
index 10a1d1a186..4e142f8cae 100644
--- a/src/Billing/Services/Implementations/SubscriptionUpdatedHandler.cs
+++ b/src/Billing/Services/Implementations/SubscriptionUpdatedHandler.cs
@@ -59,7 +59,7 @@ public class SubscriptionUpdatedHandler : ISubscriptionUpdatedHandler
     /// <param name="parsedEvent"></param>
     public async Task HandleAsync(Event parsedEvent)
     {
-        var subscription = await _stripeEventService.GetSubscription(parsedEvent, true, ["customer", "discounts"]);
+        var subscription = await _stripeEventService.GetSubscription(parsedEvent, true, ["customer", "discounts", "latest_invoice"]);
         var (organizationId, userId, providerId) = _stripeEventUtilityService.GetIdsFromMetadata(subscription.Metadata);
 
         switch (subscription.Status)
@@ -68,7 +68,8 @@ public class SubscriptionUpdatedHandler : ISubscriptionUpdatedHandler
                 when organizationId.HasValue:
                 {
                     await _organizationService.DisableAsync(organizationId.Value, subscription.CurrentPeriodEnd);
-                    if (subscription.Status == StripeSubscriptionStatus.Unpaid)
+                    if (subscription.Status == StripeSubscriptionStatus.Unpaid &&
+                        subscription.LatestInvoice is { BillingReason: "subscription_cycle" or "subscription_create" })
                     {
                         await ScheduleCancellationJobAsync(subscription.Id, organizationId.Value);
                     }
@@ -96,7 +97,10 @@ public class SubscriptionUpdatedHandler : ISubscriptionUpdatedHandler
                 {
                     await _organizationEnableCommand.EnableAsync(organizationId.Value);
                     var organization = await _organizationRepository.GetByIdAsync(organizationId.Value);
-                    await _pushNotificationService.PushSyncOrganizationStatusAsync(organization);
+                    if (organization != null)
+                    {
+                        await _pushNotificationService.PushSyncOrganizationStatusAsync(organization);
+                    }
                     break;
                 }
             case StripeSubscriptionStatus.Active:
@@ -204,23 +208,24 @@ public class SubscriptionUpdatedHandler : ISubscriptionUpdatedHandler
     private async Task ScheduleCancellationJobAsync(string subscriptionId, Guid organizationId)
     {
         var isResellerManagedOrgAlertEnabled = _featureService.IsEnabled(FeatureFlagKeys.ResellerManagedOrgAlert);
-
-        if (isResellerManagedOrgAlertEnabled)
+        if (!isResellerManagedOrgAlertEnabled)
         {
-            var scheduler = await _schedulerFactory.GetScheduler();
-
-            var job = JobBuilder.Create<SubscriptionCancellationJob>()
-                .WithIdentity($"cancel-sub-{subscriptionId}", "subscription-cancellations")
-                .UsingJobData("subscriptionId", subscriptionId)
-                .UsingJobData("organizationId", organizationId.ToString())
-                .Build();
-
-            var trigger = TriggerBuilder.Create()
-                .WithIdentity($"cancel-trigger-{subscriptionId}", "subscription-cancellations")
-                .StartAt(DateTimeOffset.UtcNow.AddDays(7))
-                .Build();
-
-            await scheduler.ScheduleJob(job, trigger);
+            return;
         }
+
+        var scheduler = await _schedulerFactory.GetScheduler();
+
+        var job = JobBuilder.Create<SubscriptionCancellationJob>()
+            .WithIdentity($"cancel-sub-{subscriptionId}", "subscription-cancellations")
+            .UsingJobData("subscriptionId", subscriptionId)
+            .UsingJobData("organizationId", organizationId.ToString())
+            .Build();
+
+        var trigger = TriggerBuilder.Create()
+            .WithIdentity($"cancel-trigger-{subscriptionId}", "subscription-cancellations")
+            .StartAt(DateTimeOffset.UtcNow.AddDays(7))
+            .Build();
+
+        await scheduler.ScheduleJob(job, trigger);
     }
 }