diff --git a/src/Billing/Services/Implementations/StripeEventService.cs b/src/Billing/Services/Implementations/StripeEventService.cs
index 03ca8eeb10..03865b48fe 100644
--- a/src/Billing/Services/Implementations/StripeEventService.cs
+++ b/src/Billing/Services/Implementations/StripeEventService.cs
@@ -9,6 +9,7 @@ namespace Bit.Billing.Services.Implementations;
 
 public class StripeEventService(
     GlobalSettings globalSettings,
+    ILogger<StripeEventService> logger,
     IOrganizationRepository organizationRepository,
     IProviderRepository providerRepository,
     ISetupIntentCache setupIntentCache,
@@ -148,26 +149,36 @@ public class StripeEventService(
         {
             var setupIntent = await GetSetupIntent(localStripeEvent);
 
+            logger.LogInformation("Extracted Setup Intent ({SetupIntentId}) from Stripe 'setup_intent.succeeded' event", setupIntent.Id);
+
             var subscriberId = await setupIntentCache.GetSubscriberIdForSetupIntent(setupIntent.Id);
+
+            logger.LogInformation("Retrieved subscriber ID ({SubscriberId}) from cache for Setup Intent ({SetupIntentId})", subscriberId, setupIntent.Id);
+
             if (subscriberId == null)
             {
+                logger.LogError("Cached subscriber ID for Setup Intent ({SetupIntentId}) is null", setupIntent.Id);
                 return null;
             }
 
             var organization = await organizationRepository.GetByIdAsync(subscriberId.Value);
+            logger.LogInformation("Retrieved organization ({OrganizationId}) via subscriber ID for Setup Intent ({SetupIntentId})", organization?.Id, setupIntent.Id);
             if (organization is { GatewayCustomerId: not null })
             {
                 var organizationCustomer = await stripeFacade.GetCustomer(organization.GatewayCustomerId);
+                logger.LogInformation("Retrieved customer ({CustomerId}) via organization ID for Setup Intent ({SetupIntentId})", organization.Id, setupIntent.Id);
                 return organizationCustomer.Metadata;
             }
 
             var provider = await providerRepository.GetByIdAsync(subscriberId.Value);
+            logger.LogInformation("Retrieved provider ({ProviderId}) via subscriber ID for Setup Intent ({SetupIntentId})", provider?.Id, setupIntent.Id);
             if (provider is not { GatewayCustomerId: not null })
             {
                 return null;
             }
 
             var providerCustomer = await stripeFacade.GetCustomer(provider.GatewayCustomerId);
+            logger.LogInformation("Retrieved customer ({CustomerId}) via provider ID for Setup Intent ({SetupIntentId})", provider.Id, setupIntent.Id);
             return providerCustomer.Metadata;
         }
     }
diff --git a/src/Core/Billing/Caches/Implementations/SetupIntentDistributedCache.cs b/src/Core/Billing/Caches/Implementations/SetupIntentDistributedCache.cs
index 8833c928fe..514898e53c 100644
--- a/src/Core/Billing/Caches/Implementations/SetupIntentDistributedCache.cs
+++ b/src/Core/Billing/Caches/Implementations/SetupIntentDistributedCache.cs
@@ -1,11 +1,13 @@
 using Microsoft.Extensions.Caching.Distributed;
 using Microsoft.Extensions.DependencyInjection;
+using Microsoft.Extensions.Logging;
 
 namespace Bit.Core.Billing.Caches.Implementations;
 
 public class SetupIntentDistributedCache(
     [FromKeyedServices("persistent")]
-    IDistributedCache distributedCache) : ISetupIntentCache
+    IDistributedCache distributedCache,
+    ILogger<SetupIntentDistributedCache> logger) : ISetupIntentCache
 {
     public async Task<string?> GetSetupIntentIdForSubscriber(Guid subscriberId)
     {
@@ -17,11 +19,12 @@ public class SetupIntentDistributedCache(
     {
         var cacheKey = GetCacheKeyBySetupIntentId(setupIntentId);
         var value = await distributedCache.GetStringAsync(cacheKey);
-        if (string.IsNullOrEmpty(value) || !Guid.TryParse(value, out var subscriberId))
+        if (!string.IsNullOrEmpty(value) && Guid.TryParse(value, out var subscriberId))
         {
-            return null;
+            return subscriberId;
         }
-        return subscriberId;
+        logger.LogError("Subscriber ID value ({Value}) cached for Setup Intent ({SetupIntentId}) is null or not a valid Guid", value, setupIntentId);
+        return null;
     }
 
     public async Task RemoveSetupIntentForSubscriber(Guid subscriberId)
diff --git a/src/Core/Billing/Payment/Commands/UpdatePaymentMethodCommand.cs b/src/Core/Billing/Payment/Commands/UpdatePaymentMethodCommand.cs
index a5a9e3e9c9..2166c4318c 100644
--- a/src/Core/Billing/Payment/Commands/UpdatePaymentMethodCommand.cs
+++ b/src/Core/Billing/Payment/Commands/UpdatePaymentMethodCommand.cs
@@ -94,6 +94,8 @@ public class UpdatePaymentMethodCommand(
 
         await setupIntentCache.Set(subscriber.Id, setupIntent.Id);
 
+        _logger.LogInformation("{Command}: Successfully cached Setup Intent ({SetupIntentId}) for subscriber ({SubscriberID})", CommandName, setupIntent.Id, subscriber.Id);
+
         await UnlinkBraintreeCustomerAsync(customer);
 
         return MaskedPaymentMethod.From(setupIntent);
diff --git a/test/Billing.Test/Services/StripeEventServiceTests.cs b/test/Billing.Test/Services/StripeEventServiceTests.cs
index 68aeab2f44..c438ef663c 100644
--- a/test/Billing.Test/Services/StripeEventServiceTests.cs
+++ b/test/Billing.Test/Services/StripeEventServiceTests.cs
@@ -4,6 +4,7 @@ using Bit.Core.AdminConsole.Repositories;
 using Bit.Core.Billing.Caches;
 using Bit.Core.Repositories;
 using Bit.Core.Settings;
+using Microsoft.Extensions.Logging;
 using NSubstitute;
 using Stripe;
 using Xunit;
@@ -28,7 +29,13 @@ public class StripeEventServiceTests
         _providerRepository = Substitute.For<IProviderRepository>();
         _setupIntentCache = Substitute.For<ISetupIntentCache>();
         _stripeFacade = Substitute.For<IStripeFacade>();
-        _stripeEventService = new StripeEventService(globalSettings, _organizationRepository, _providerRepository, _setupIntentCache, _stripeFacade);
+        _stripeEventService = new StripeEventService(
+            globalSettings,
+            Substitute.For<ILogger<StripeEventService>>(),
+            _organizationRepository,
+            _providerRepository,
+            _setupIntentCache,
+            _stripeFacade);
     }
 
     #region GetCharge