diff --git a/src/Api/AdminConsole/Models/Request/Organizations/OrganizationCreateRequestModel.cs b/src/Api/AdminConsole/Models/Request/Organizations/OrganizationCreateRequestModel.cs
index 2ea4e8b84..304978eb1 100644
--- a/src/Api/AdminConsole/Models/Request/Organizations/OrganizationCreateRequestModel.cs
+++ b/src/Api/AdminConsole/Models/Request/Organizations/OrganizationCreateRequestModel.cs
@@ -46,6 +46,7 @@ public class OrganizationCreateRequestModel : IValidatableObject
     public int? AdditionalServiceAccounts { get; set; }
     [Required]
     public bool UseSecretsManager { get; set; }
+    public bool IsFromSecretsManagerTrial { get; set; }
 
     public virtual OrganizationSignup ToOrganizationSignup(User user)
     {
@@ -67,6 +68,7 @@ public class OrganizationCreateRequestModel : IValidatableObject
             AdditionalSmSeats = AdditionalSmSeats.GetValueOrDefault(),
             AdditionalServiceAccounts = AdditionalServiceAccounts.GetValueOrDefault(),
             UseSecretsManager = UseSecretsManager,
+            IsFromSecretsManagerTrial = IsFromSecretsManagerTrial,
             TaxInfo = new TaxInfo
             {
                 TaxIdNumber = TaxIdNumber,
diff --git a/src/Api/Models/Response/SubscriptionResponseModel.cs b/src/Api/Models/Response/SubscriptionResponseModel.cs
index bac1cf3f9..7ba2b857e 100644
--- a/src/Api/Models/Response/SubscriptionResponseModel.cs
+++ b/src/Api/Models/Response/SubscriptionResponseModel.cs
@@ -50,11 +50,13 @@ public class BillingCustomerDiscount
         Id = discount.Id;
         Active = discount.Active;
         PercentOff = discount.PercentOff;
+        AppliesTo = discount.AppliesTo;
     }
 
     public string Id { get; }
     public bool Active { get; }
     public decimal? PercentOff { get; }
+    public List<string> AppliesTo { get; }
 }
 
 public class BillingSubscription
@@ -89,6 +91,7 @@ public class BillingSubscription
     {
         public BillingSubscriptionItem(SubscriptionInfo.BillingSubscription.BillingSubscriptionItem item)
         {
+            ProductId = item.ProductId;
             Name = item.Name;
             Amount = item.Amount;
             Interval = item.Interval;
@@ -97,6 +100,7 @@ public class BillingSubscription
             AddonSubscriptionItem = item.AddonSubscriptionItem;
         }
 
+        public string ProductId { get; set; }
         public string Name { get; set; }
         public decimal Amount { get; set; }
         public int Quantity { get; set; }
diff --git a/src/Core/AdminConsole/Services/Implementations/OrganizationService.cs b/src/Core/AdminConsole/Services/Implementations/OrganizationService.cs
index f97bd7c07..8ab5293e9 100644
--- a/src/Core/AdminConsole/Services/Implementations/OrganizationService.cs
+++ b/src/Core/AdminConsole/Services/Implementations/OrganizationService.cs
@@ -517,7 +517,7 @@ public class OrganizationService : IOrganizationService
             await _paymentService.PurchaseOrganizationAsync(organization, signup.PaymentMethodType.Value,
                 signup.PaymentToken, plan, signup.AdditionalStorageGb, signup.AdditionalSeats,
                 signup.PremiumAccessAddon, signup.TaxInfo, provider, signup.AdditionalSmSeats.GetValueOrDefault(),
-                signup.AdditionalServiceAccounts.GetValueOrDefault());
+                signup.AdditionalServiceAccounts.GetValueOrDefault(), signup.IsFromSecretsManagerTrial);
         }
 
         var ownerId = provider ? default : signup.Owner.Id;
diff --git a/src/Core/Models/Business/OrganizationUpgrade.cs b/src/Core/Models/Business/OrganizationUpgrade.cs
index 173502a24..6992f492a 100644
--- a/src/Core/Models/Business/OrganizationUpgrade.cs
+++ b/src/Core/Models/Business/OrganizationUpgrade.cs
@@ -15,4 +15,5 @@ public class OrganizationUpgrade
     public int? AdditionalSmSeats { get; set; }
     public int? AdditionalServiceAccounts { get; set; }
     public bool UseSecretsManager { get; set; }
+    public bool IsFromSecretsManagerTrial { get; set; }
 }
diff --git a/src/Core/Models/Business/SubscriptionInfo.cs b/src/Core/Models/Business/SubscriptionInfo.cs
index e23108123..e2a689f61 100644
--- a/src/Core/Models/Business/SubscriptionInfo.cs
+++ b/src/Core/Models/Business/SubscriptionInfo.cs
@@ -17,11 +17,13 @@ public class SubscriptionInfo
             Id = discount.Id;
             Active = discount.Start != null && discount.End == null;
             PercentOff = discount.Coupon?.PercentOff;
+            AppliesTo = discount.Coupon?.AppliesTo?.Products ?? new List<string>();
         }
 
         public string Id { get; }
         public bool Active { get; }
         public decimal? PercentOff { get; }
+        public List<string> AppliesTo { get; }
     }
 
     public class BillingSubscription
@@ -59,6 +61,7 @@ public class SubscriptionInfo
             {
                 if (item.Plan != null)
                 {
+                    ProductId = item.Plan.ProductId;
                     Name = item.Plan.Nickname;
                     Amount = item.Plan.Amount.GetValueOrDefault() / 100M;
                     Interval = item.Plan.Interval;
@@ -72,6 +75,7 @@ public class SubscriptionInfo
 
             public bool AddonSubscriptionItem { get; set; }
 
+            public string ProductId { get; set; }
             public string Name { get; set; }
             public decimal Amount { get; set; }
             public int Quantity { get; set; }
diff --git a/src/Core/Services/IPaymentService.cs b/src/Core/Services/IPaymentService.cs
index 70cc88c20..f8f24cfbd 100644
--- a/src/Core/Services/IPaymentService.cs
+++ b/src/Core/Services/IPaymentService.cs
@@ -12,7 +12,7 @@ public interface IPaymentService
     Task<string> PurchaseOrganizationAsync(Organization org, PaymentMethodType paymentMethodType,
         string paymentToken, Plan plan, short additionalStorageGb, int additionalSeats,
         bool premiumAccessAddon, TaxInfo taxInfo, bool provider = false, int additionalSmSeats = 0,
-        int additionalServiceAccount = 0);
+        int additionalServiceAccount = 0, bool signupIsFromSecretsManagerTrial = false);
     Task SponsorOrganizationAsync(Organization org, OrganizationSponsorship sponsorship);
     Task RemoveOrganizationSponsorshipAsync(Organization org, OrganizationSponsorship sponsorship);
     Task<string> UpgradeFreeOrganizationAsync(Organization org, Plan plan, OrganizationUpgrade upgrade);
diff --git a/src/Core/Services/Implementations/StripePaymentService.cs b/src/Core/Services/Implementations/StripePaymentService.cs
index cc960083a..f3a939650 100644
--- a/src/Core/Services/Implementations/StripePaymentService.cs
+++ b/src/Core/Services/Implementations/StripePaymentService.cs
@@ -7,6 +7,7 @@ using Bit.Core.Models.Business;
 using Bit.Core.Repositories;
 using Bit.Core.Settings;
 using Microsoft.Extensions.Logging;
+using Stripe;
 using StaticStore = Bit.Core.Models.StaticStore;
 using TaxRate = Bit.Core.Entities.TaxRate;
 
@@ -17,6 +18,7 @@ public class StripePaymentService : IPaymentService
     private const string PremiumPlanId = "premium-annually";
     private const string StoragePlanId = "storage-gb-annually";
     private const string ProviderDiscountId = "msp-discount-35";
+    private const string SecretsManagerStandaloneDiscountId = "sm-standalone";
 
     private readonly ITransactionRepository _transactionRepository;
     private readonly IUserRepository _userRepository;
@@ -47,7 +49,7 @@ public class StripePaymentService : IPaymentService
     public async Task<string> PurchaseOrganizationAsync(Organization org, PaymentMethodType paymentMethodType,
         string paymentToken, StaticStore.Plan plan, short additionalStorageGb,
         int additionalSeats, bool premiumAccessAddon, TaxInfo taxInfo, bool provider = false,
-        int additionalSmSeats = 0, int additionalServiceAccount = 0)
+        int additionalSmSeats = 0, int additionalServiceAccount = 0, bool signupIsFromSecretsManagerTrial = false)
     {
         Braintree.Customer braintreeCustomer = null;
         string stipeCustomerSourceToken = null;
@@ -124,7 +126,11 @@ public class StripePaymentService : IPaymentService
                         },
                     },
                 },
-                Coupon = provider ? ProviderDiscountId : null,
+                Coupon = signupIsFromSecretsManagerTrial
+                    ? SecretsManagerStandaloneDiscountId
+                    : provider
+                        ? ProviderDiscountId
+                        : null,
                 Address = new Stripe.AddressOptions
                 {
                     Country = taxInfo.BillingAddressCountry,
@@ -1410,7 +1416,9 @@ public class StripePaymentService : IPaymentService
 
         if (!string.IsNullOrWhiteSpace(subscriber.GatewayCustomerId))
         {
-            var customer = await _stripeAdapter.CustomerGetAsync(subscriber.GatewayCustomerId);
+            var customerGetOptions = new CustomerGetOptions();
+            customerGetOptions.AddExpand("discount.coupon.applies_to");
+            var customer = await _stripeAdapter.CustomerGetAsync(subscriber.GatewayCustomerId, customerGetOptions);
 
             if (customer.Discount != null)
             {
@@ -1418,29 +1426,36 @@ public class StripePaymentService : IPaymentService
             }
         }
 
-        if (!string.IsNullOrWhiteSpace(subscriber.GatewaySubscriptionId))
+        if (string.IsNullOrWhiteSpace(subscriber.GatewaySubscriptionId))
         {
-            var sub = await _stripeAdapter.SubscriptionGetAsync(subscriber.GatewaySubscriptionId);
-            if (sub != null)
-            {
-                subscriptionInfo.Subscription = new SubscriptionInfo.BillingSubscription(sub);
-            }
+            return subscriptionInfo;
+        }
 
-            if (!sub.CanceledAt.HasValue && !string.IsNullOrWhiteSpace(subscriber.GatewayCustomerId))
+        var sub = await _stripeAdapter.SubscriptionGetAsync(subscriber.GatewaySubscriptionId);
+        if (sub != null)
+        {
+            subscriptionInfo.Subscription = new SubscriptionInfo.BillingSubscription(sub);
+        }
+
+        if (sub is { CanceledAt: not null } || string.IsNullOrWhiteSpace(subscriber.GatewayCustomerId))
+        {
+            return subscriptionInfo;
+        }
+
+        try
+        {
+            var upcomingInvoiceOptions = new UpcomingInvoiceOptions { Customer = subscriber.GatewayCustomerId };
+            var upcomingInvoice = await _stripeAdapter.InvoiceUpcomingAsync(upcomingInvoiceOptions);
+
+            if (upcomingInvoice != null)
             {
-                try
-                {
-                    var upcomingInvoice = await _stripeAdapter.InvoiceUpcomingAsync(
-                        new Stripe.UpcomingInvoiceOptions { Customer = subscriber.GatewayCustomerId });
-                    if (upcomingInvoice != null)
-                    {
-                        subscriptionInfo.UpcomingInvoice =
-                            new SubscriptionInfo.BillingUpcomingInvoice(upcomingInvoice);
-                    }
-                }
-                catch (Stripe.StripeException) { }
+                subscriptionInfo.UpcomingInvoice = new SubscriptionInfo.BillingUpcomingInvoice(upcomingInvoice);
             }
         }
+        catch (StripeException ex)
+        {
+            _logger.LogWarning(ex, "Encountered an unexpected Stripe error");
+        }
 
         return subscriptionInfo;
     }
diff --git a/test/Core.Test/AdminConsole/Services/OrganizationServiceTests.cs b/test/Core.Test/AdminConsole/Services/OrganizationServiceTests.cs
index 52dce5802..5f6aa0866 100644
--- a/test/Core.Test/AdminConsole/Services/OrganizationServiceTests.cs
+++ b/test/Core.Test/AdminConsole/Services/OrganizationServiceTests.cs
@@ -209,6 +209,7 @@ public class OrganizationServiceTests
         signup.PaymentMethodType = PaymentMethodType.Card;
         signup.PremiumAccessAddon = false;
         signup.UseSecretsManager = false;
+        signup.IsFromSecretsManagerTrial = false;
 
         var purchaseOrganizationPlan = StaticStore.GetPlan(signup.Plan);
 
@@ -247,7 +248,8 @@ public class OrganizationServiceTests
             signup.TaxInfo,
             false,
             signup.AdditionalSmSeats.GetValueOrDefault(),
-            signup.AdditionalServiceAccounts.GetValueOrDefault()
+            signup.AdditionalServiceAccounts.GetValueOrDefault(),
+            signup.UseSecretsManager
         );
     }
 
@@ -326,6 +328,7 @@ public class OrganizationServiceTests
         signup.AdditionalServiceAccounts = 20;
         signup.PaymentMethodType = PaymentMethodType.Card;
         signup.PremiumAccessAddon = false;
+        signup.IsFromSecretsManagerTrial = false;
 
         var result = await sutProvider.Sut.SignUpAsync(signup);
 
@@ -362,7 +365,8 @@ public class OrganizationServiceTests
             signup.TaxInfo,
             false,
             signup.AdditionalSmSeats.GetValueOrDefault(),
-            signup.AdditionalServiceAccounts.GetValueOrDefault()
+            signup.AdditionalServiceAccounts.GetValueOrDefault(),
+            signup.IsFromSecretsManagerTrial
         );
     }