diff --git a/src/Core/OrganizationFeatures/OrganizationSubscriptions/UpgradeOrganizationPlanCommand.cs b/src/Core/OrganizationFeatures/OrganizationSubscriptions/UpgradeOrganizationPlanCommand.cs
index 33dd38833..7f463460d 100644
--- a/src/Core/OrganizationFeatures/OrganizationSubscriptions/UpgradeOrganizationPlanCommand.cs
+++ b/src/Core/OrganizationFeatures/OrganizationSubscriptions/UpgradeOrganizationPlanCommand.cs
@@ -231,9 +231,19 @@ public class UpgradeOrganizationPlanCommand : IUpgradeOrganizationPlanCommand
             }
             else
             {
-                paymentIntentClientSecret = await _paymentService.UpgradeFreeOrganizationAsync(organization,
-                    newPlan, upgrade);
-                success = string.IsNullOrWhiteSpace(paymentIntentClientSecret);
+                try
+                {
+                    paymentIntentClientSecret = await _paymentService.UpgradeFreeOrganizationAsync(organization,
+                        newPlan, upgrade);
+                    success = string.IsNullOrWhiteSpace(paymentIntentClientSecret);
+                }
+                catch
+                {
+                    await _paymentService.CancelAndRecoverChargesAsync(organization);
+                    organization.GatewayCustomerId = null;
+                    await _organizationService.ReplaceAndUpdateCacheAsync(organization);
+                    throw;
+                }
             }
         }
         else