diff --git a/src/Api/Billing/Controllers/OrganizationBillingController.cs b/src/Api/Billing/Controllers/OrganizationBillingController.cs
index 7da0a0f602..1c0cfd9388 100644
--- a/src/Api/Billing/Controllers/OrganizationBillingController.cs
+++ b/src/Api/Billing/Controllers/OrganizationBillingController.cs
@@ -1,7 +1,9 @@
 #nullable enable
+using Bit.Api.AdminConsole.Models.Request.Organizations;
 using Bit.Api.Billing.Models.Requests;
 using Bit.Api.Billing.Models.Responses;
 using Bit.Core;
+using Bit.Core.Billing.Models.Sales;
 using Bit.Core.Billing.Services;
 using Bit.Core.Context;
 using Bit.Core.Repositories;
@@ -21,7 +23,8 @@ public class OrganizationBillingController(
     IOrganizationRepository organizationRepository,
     IPaymentService paymentService,
     ISubscriberService subscriberService,
-    IPaymentHistoryService paymentHistoryService) : BaseBillingController
+    IPaymentHistoryService paymentHistoryService,
+    IUserService userService) : BaseBillingController
 {
     [HttpGet("metadata")]
     public async Task<IResult> GetMetadataAsync([FromRoute] Guid organizationId)
@@ -278,4 +281,37 @@ public class OrganizationBillingController(
 
         return TypedResults.Ok();
     }
+
+    [HttpPost("restart-subscription")]
+    public async Task<IResult> RestartSubscriptionAsync([FromRoute] Guid organizationId,
+        [FromBody] OrganizationCreateRequestModel model)
+    {
+        var user = await userService.GetUserByPrincipalAsync(User);
+        if (user == null)
+        {
+            throw new UnauthorizedAccessException();
+        }
+
+        if (!featureService.IsEnabled(FeatureFlagKeys.AC2476_DeprecateStripeSourcesAPI))
+        {
+            return Error.NotFound();
+        }
+
+        if (!await currentContext.EditPaymentMethods(organizationId))
+        {
+            return Error.Unauthorized();
+        }
+
+        var organization = await organizationRepository.GetByIdAsync(organizationId);
+
+        if (organization == null)
+        {
+            return Error.NotFound();
+        }
+        var organizationSignup = model.ToOrganizationSignup(user);
+        var sale = OrganizationSale.From(organization, organizationSignup);
+        await organizationBillingService.Finalize(sale);
+
+        return TypedResults.Ok();
+    }
 }
diff --git a/src/Api/Billing/Models/Responses/OrganizationMetadataResponse.cs b/src/Api/Billing/Models/Responses/OrganizationMetadataResponse.cs
index 28f156fa39..1dfc79be21 100644
--- a/src/Api/Billing/Models/Responses/OrganizationMetadataResponse.cs
+++ b/src/Api/Billing/Models/Responses/OrganizationMetadataResponse.cs
@@ -9,6 +9,7 @@ public record OrganizationMetadataResponse(
     bool IsSubscriptionUnpaid,
     bool HasSubscription,
     bool HasOpenInvoice,
+    bool IsSubscriptionCanceled,
     DateTime? InvoiceDueDate,
     DateTime? InvoiceCreatedDate,
     DateTime? SubPeriodEndDate)
@@ -21,6 +22,7 @@ public record OrganizationMetadataResponse(
             metadata.IsSubscriptionUnpaid,
             metadata.HasSubscription,
             metadata.HasOpenInvoice,
+            metadata.IsSubscriptionCanceled,
             metadata.InvoiceDueDate,
             metadata.InvoiceCreatedDate,
             metadata.SubPeriodEndDate);
diff --git a/src/Core/Billing/Models/OrganizationMetadata.cs b/src/Core/Billing/Models/OrganizationMetadata.cs
index b6442e4c19..4bb9a85825 100644
--- a/src/Core/Billing/Models/OrganizationMetadata.cs
+++ b/src/Core/Billing/Models/OrganizationMetadata.cs
@@ -7,6 +7,7 @@ public record OrganizationMetadata(
     bool IsSubscriptionUnpaid,
     bool HasSubscription,
     bool HasOpenInvoice,
+    bool IsSubscriptionCanceled,
     DateTime? InvoiceDueDate,
     DateTime? InvoiceCreatedDate,
     DateTime? SubPeriodEndDate);
diff --git a/src/Core/Billing/Services/Implementations/OrganizationBillingService.cs b/src/Core/Billing/Services/Implementations/OrganizationBillingService.cs
index 8114d5ba65..ec9770c59e 100644
--- a/src/Core/Billing/Services/Implementations/OrganizationBillingService.cs
+++ b/src/Core/Billing/Services/Implementations/OrganizationBillingService.cs
@@ -69,7 +69,7 @@ public class OrganizationBillingService(
         if (string.IsNullOrWhiteSpace(organization.GatewaySubscriptionId))
         {
             return new OrganizationMetadata(isEligibleForSelfHost, isManaged, false,
-                false, false, false, null, null, null);
+                false, false, false, false, null, null, null);
         }
 
         var customer = await subscriberService.GetCustomer(organization,
@@ -79,6 +79,7 @@ public class OrganizationBillingService(
 
         var isOnSecretsManagerStandalone = IsOnSecretsManagerStandalone(organization, customer, subscription);
         var isSubscriptionUnpaid = IsSubscriptionUnpaid(subscription);
+        var isSubscriptionCanceled = IsSubscriptionCanceled(subscription);
         var hasSubscription = true;
         var openInvoice = await HasOpenInvoiceAsync(subscription);
         var hasOpenInvoice = openInvoice.HasOpenInvoice;
@@ -87,7 +88,7 @@ public class OrganizationBillingService(
         var subPeriodEndDate = subscription?.CurrentPeriodEnd;
 
         return new OrganizationMetadata(isEligibleForSelfHost, isManaged, isOnSecretsManagerStandalone,
-            isSubscriptionUnpaid, hasSubscription, hasOpenInvoice, invoiceDueDate, invoiceCreatedDate, subPeriodEndDate);
+            isSubscriptionUnpaid, hasSubscription, hasOpenInvoice, isSubscriptionCanceled, invoiceDueDate, invoiceCreatedDate, subPeriodEndDate);
     }
 
     public async Task UpdatePaymentMethod(
@@ -437,5 +438,15 @@ public class OrganizationBillingService(
             ? (true, invoice.Created, invoice.DueDate)
             : (false, null, null);
     }
+
+    private static bool IsSubscriptionCanceled(Subscription subscription)
+    {
+        if (subscription == null)
+        {
+            return false;
+        }
+
+        return subscription.Status == "canceled";
+    }
     #endregion
 }
diff --git a/test/Api.Test/Billing/Controllers/OrganizationBillingControllerTests.cs b/test/Api.Test/Billing/Controllers/OrganizationBillingControllerTests.cs
index d500fb354a..a8c3cf15a9 100644
--- a/test/Api.Test/Billing/Controllers/OrganizationBillingControllerTests.cs
+++ b/test/Api.Test/Billing/Controllers/OrganizationBillingControllerTests.cs
@@ -52,7 +52,7 @@ public class OrganizationBillingControllerTests
     {
         sutProvider.GetDependency<ICurrentContext>().OrganizationUser(organizationId).Returns(true);
         sutProvider.GetDependency<IOrganizationBillingService>().GetMetadata(organizationId)
-            .Returns(new OrganizationMetadata(true, true, true, true, true, true, null, null, null));
+            .Returns(new OrganizationMetadata(true, true, true, true, true, true, true, null, null, null));
 
         var result = await sutProvider.Sut.GetMetadataAsync(organizationId);