diff --git a/src/Billing/Jobs/JobsHostedService.cs b/src/Billing/Jobs/JobsHostedService.cs
index d91ca21520..a6e702c662 100644
--- a/src/Billing/Jobs/JobsHostedService.cs
+++ b/src/Billing/Jobs/JobsHostedService.cs
@@ -32,5 +32,6 @@ public class JobsHostedService : BaseJobsHostedService
     public static void AddJobsServices(IServiceCollection services)
     {
         services.AddTransient<AliveJob>();
+        services.AddTransient<SubscriptionCancellationJob>();
     }
 }
diff --git a/src/Billing/Jobs/SubscriptionCancellationJob.cs b/src/Billing/Jobs/SubscriptionCancellationJob.cs
new file mode 100644
index 0000000000..c46581272e
--- /dev/null
+++ b/src/Billing/Jobs/SubscriptionCancellationJob.cs
@@ -0,0 +1,58 @@
+using Bit.Billing.Services;
+using Bit.Core.Repositories;
+using Quartz;
+using Stripe;
+
+namespace Bit.Billing.Jobs;
+
+public class SubscriptionCancellationJob(
+    IStripeFacade stripeFacade,
+    IOrganizationRepository organizationRepository)
+    : IJob
+{
+    public async Task Execute(IJobExecutionContext context)
+    {
+        var subscriptionId = context.MergedJobDataMap.GetString("subscriptionId");
+        var organizationId = new Guid(context.MergedJobDataMap.GetString("organizationId") ?? string.Empty);
+
+        var organization = await organizationRepository.GetByIdAsync(organizationId);
+        if (organization == null || organization.Enabled)
+        {
+            // Organization was deleted or re-enabled by CS, skip cancellation
+            return;
+        }
+
+        var subscription = await stripeFacade.GetSubscription(subscriptionId);
+        if (subscription?.Status != "unpaid")
+        {
+            // Subscription is no longer unpaid, skip cancellation
+            return;
+        }
+
+        // Cancel the subscription
+        await stripeFacade.CancelSubscription(subscriptionId, new SubscriptionCancelOptions());
+
+        // Void any open invoices
+        var options = new InvoiceListOptions
+        {
+            Status = "open",
+            Subscription = subscriptionId,
+            Limit = 100
+        };
+        var invoices = await stripeFacade.ListInvoices(options);
+        foreach (var invoice in invoices)
+        {
+            await stripeFacade.VoidInvoice(invoice.Id);
+        }
+
+        while (invoices.HasMore)
+        {
+            options.StartingAfter = invoices.Data.Last().Id;
+            invoices = await stripeFacade.ListInvoices(options);
+            foreach (var invoice in invoices)
+            {
+                await stripeFacade.VoidInvoice(invoice.Id);
+            }
+        }
+    }
+}
diff --git a/src/Billing/Services/Implementations/SubscriptionUpdatedHandler.cs b/src/Billing/Services/Implementations/SubscriptionUpdatedHandler.cs
index 6b4fef43d1..ea277a6307 100644
--- a/src/Billing/Services/Implementations/SubscriptionUpdatedHandler.cs
+++ b/src/Billing/Services/Implementations/SubscriptionUpdatedHandler.cs
@@ -1,9 +1,12 @@
 using Bit.Billing.Constants;
+using Bit.Billing.Jobs;
+using Bit.Core;
 using Bit.Core.OrganizationFeatures.OrganizationSponsorships.FamiliesForEnterprise.Interfaces;
 using Bit.Core.Platform.Push;
 using Bit.Core.Repositories;
 using Bit.Core.Services;
 using Bit.Core.Utilities;
+using Quartz;
 using Stripe;
 using Event = Stripe.Event;
 
@@ -19,6 +22,8 @@ public class SubscriptionUpdatedHandler : ISubscriptionUpdatedHandler
     private readonly IUserService _userService;
     private readonly IPushNotificationService _pushNotificationService;
     private readonly IOrganizationRepository _organizationRepository;
+    private readonly ISchedulerFactory _schedulerFactory;
+    private readonly IFeatureService _featureService;
 
     public SubscriptionUpdatedHandler(
         IStripeEventService stripeEventService,
@@ -28,7 +33,9 @@ public class SubscriptionUpdatedHandler : ISubscriptionUpdatedHandler
         IOrganizationSponsorshipRenewCommand organizationSponsorshipRenewCommand,
         IUserService userService,
         IPushNotificationService pushNotificationService,
-        IOrganizationRepository organizationRepository)
+        IOrganizationRepository organizationRepository,
+        ISchedulerFactory schedulerFactory,
+        IFeatureService featureService)
     {
         _stripeEventService = stripeEventService;
         _stripeEventUtilityService = stripeEventUtilityService;
@@ -38,6 +45,8 @@ public class SubscriptionUpdatedHandler : ISubscriptionUpdatedHandler
         _userService = userService;
         _pushNotificationService = pushNotificationService;
         _organizationRepository = organizationRepository;
+        _schedulerFactory = schedulerFactory;
+        _featureService = featureService;
     }
 
     /// <summary>
@@ -55,6 +64,10 @@ public class SubscriptionUpdatedHandler : ISubscriptionUpdatedHandler
                 when organizationId.HasValue:
                 {
                     await _organizationService.DisableAsync(organizationId.Value, subscription.CurrentPeriodEnd);
+                    if (subscription.Status == StripeSubscriptionStatus.Unpaid)
+                    {
+                        await ScheduleCancellationJobAsync(subscription.Id, organizationId.Value);
+                    }
                     break;
                 }
             case StripeSubscriptionStatus.Unpaid or StripeSubscriptionStatus.IncompleteExpired:
@@ -183,4 +196,27 @@ public class SubscriptionUpdatedHandler : ISubscriptionUpdatedHandler
             await _stripeFacade.DeleteSubscriptionDiscount(subscription.Id);
         }
     }
+
+    private async Task ScheduleCancellationJobAsync(string subscriptionId, Guid organizationId)
+    {
+        var isResellerManagedOrgAlertEnabled = _featureService.IsEnabled(FeatureFlagKeys.ResellerManagedOrgAlert);
+
+        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);
+        }
+    }
 }
diff --git a/src/Billing/Startup.cs b/src/Billing/Startup.cs
index e3547d943b..2d2f109e77 100644
--- a/src/Billing/Startup.cs
+++ b/src/Billing/Startup.cs
@@ -9,6 +9,7 @@ using Bit.Core.Settings;
 using Bit.Core.Utilities;
 using Bit.SharedWeb.Utilities;
 using Microsoft.Extensions.DependencyInjection.Extensions;
+using Quartz;
 using Stripe;
 
 namespace Bit.Billing;
@@ -101,6 +102,13 @@ public class Startup
         services.AddScoped<IStripeEventService, StripeEventService>();
         services.AddScoped<IProviderEventService, ProviderEventService>();
 
+        // Add Quartz services first
+        services.AddQuartz(q =>
+        {
+            q.UseMicrosoftDependencyInjectionJobFactory();
+        });
+        services.AddQuartzHostedService();
+
         // Jobs service
         Jobs.JobsHostedService.AddJobsServices(services);
         services.AddHostedService<Jobs.JobsHostedService>();
diff --git a/src/Core/Core.csproj b/src/Core/Core.csproj
index ddd9fc26bb..7a5f7e2543 100644
--- a/src/Core/Core.csproj
+++ b/src/Core/Core.csproj
@@ -67,6 +67,9 @@
     <PackageReference Include="YubicoDotNetClient" Version="1.2.0" />
     <PackageReference Include="Microsoft.Extensions.Caching.StackExchangeRedis" Version="8.0.10" />
     <PackageReference Include="LaunchDarkly.ServerSdk" Version="8.6.0" />
+    <PackageReference Include="Quartz" Version="3.13.1" />
+    <PackageReference Include="Quartz.Extensions.Hosting" Version="3.13.1" />
+    <PackageReference Include="Quartz.Extensions.DependencyInjection" Version="3.13.1" />
   </ItemGroup>
 
   <ItemGroup>