diff --git a/bitwarden_license/src/Commercial.Core/AdminConsole/Services/ProviderService.cs b/bitwarden_license/src/Commercial.Core/AdminConsole/Services/ProviderService.cs
index dd97aaca04..b6773f0bd4 100644
--- a/bitwarden_license/src/Commercial.Core/AdminConsole/Services/ProviderService.cs
+++ b/bitwarden_license/src/Commercial.Core/AdminConsole/Services/ProviderService.cs
@@ -551,7 +551,7 @@ public class ProviderService : IProviderService
 
         var (organization, _, defaultCollection) = consolidatedBillingEnabled
             ? await _organizationService.SignupClientAsync(organizationSignup)
-            : await _organizationService.SignUpAsync(organizationSignup, true);
+            : await _organizationService.SignUpAsync(organizationSignup);
 
         var providerOrganization = new ProviderOrganization
         {
diff --git a/bitwarden_license/test/Commercial.Core.Test/AdminConsole/Services/ProviderServiceTests.cs b/bitwarden_license/test/Commercial.Core.Test/AdminConsole/Services/ProviderServiceTests.cs
index 4beda0060d..4aac363b9c 100644
--- a/bitwarden_license/test/Commercial.Core.Test/AdminConsole/Services/ProviderServiceTests.cs
+++ b/bitwarden_license/test/Commercial.Core.Test/AdminConsole/Services/ProviderServiceTests.cs
@@ -667,7 +667,7 @@ public class ProviderServiceTests
 
         sutProvider.GetDependency<IProviderRepository>().GetByIdAsync(provider.Id).Returns(provider);
         var providerOrganizationRepository = sutProvider.GetDependency<IProviderOrganizationRepository>();
-        sutProvider.GetDependency<IOrganizationService>().SignUpAsync(organizationSignup, true)
+        sutProvider.GetDependency<IOrganizationService>().SignUpAsync(organizationSignup)
             .Returns((organization, null as OrganizationUser, new Collection()));
 
         var providerOrganization =
@@ -775,7 +775,7 @@ public class ProviderServiceTests
 
         sutProvider.GetDependency<IProviderRepository>().GetByIdAsync(provider.Id).Returns(provider);
         var providerOrganizationRepository = sutProvider.GetDependency<IProviderOrganizationRepository>();
-        sutProvider.GetDependency<IOrganizationService>().SignUpAsync(organizationSignup, true)
+        sutProvider.GetDependency<IOrganizationService>().SignUpAsync(organizationSignup)
             .Returns((organization, null as OrganizationUser, defaultCollection));
 
         var providerOrganization =
diff --git a/src/Api/AdminConsole/Controllers/ProviderOrganizationsController.cs b/src/Api/AdminConsole/Controllers/ProviderOrganizationsController.cs
index 7cdab7348a..12166c836e 100644
--- a/src/Api/AdminConsole/Controllers/ProviderOrganizationsController.cs
+++ b/src/Api/AdminConsole/Controllers/ProviderOrganizationsController.cs
@@ -84,6 +84,7 @@ public class ProviderOrganizationsController : Controller
         }
 
         var organizationSignup = model.OrganizationCreateRequest.ToOrganizationSignup(user);
+        organizationSignup.IsFromProvider = true;
         var result = await _providerService.CreateOrganizationAsync(providerId, organizationSignup, model.ClientOwnerEmail, user);
         return new ProviderOrganizationResponseModel(result);
     }
diff --git a/src/Api/Billing/Controllers/OrganizationBillingController.cs b/src/Api/Billing/Controllers/OrganizationBillingController.cs
index b1c7feb560..8d926ec9fa 100644
--- a/src/Api/Billing/Controllers/OrganizationBillingController.cs
+++ b/src/Api/Billing/Controllers/OrganizationBillingController.cs
@@ -182,11 +182,9 @@ public class OrganizationBillingController(
 
         var tokenizedPaymentSource = requestBody.PaymentSource.ToDomain();
 
-        await subscriberService.UpdatePaymentSource(organization, tokenizedPaymentSource);
-
         var taxInformation = requestBody.TaxInformation.ToDomain();
 
-        await subscriberService.UpdateTaxInformation(organization, taxInformation);
+        await organizationBillingService.UpdatePaymentMethod(organization, tokenizedPaymentSource, taxInformation);
 
         return TypedResults.Ok();
     }
diff --git a/src/Api/Billing/Controllers/ProviderClientsController.cs b/src/Api/Billing/Controllers/ProviderClientsController.cs
index d69499976e..23a6da4590 100644
--- a/src/Api/Billing/Controllers/ProviderClientsController.cs
+++ b/src/Api/Billing/Controllers/ProviderClientsController.cs
@@ -52,7 +52,8 @@ public class ProviderClientsController(
             OwnerKey = requestBody.Key,
             PublicKey = requestBody.KeyPair.PublicKey,
             PrivateKey = requestBody.KeyPair.EncryptedPrivateKey,
-            CollectionName = requestBody.CollectionName
+            CollectionName = requestBody.CollectionName,
+            IsFromProvider = true
         };
 
         var providerOrganization = await providerService.CreateOrganizationAsync(
diff --git a/src/Core/AdminConsole/Services/IOrganizationService.cs b/src/Core/AdminConsole/Services/IOrganizationService.cs
index 0780afb33e..aaa2f86c8d 100644
--- a/src/Core/AdminConsole/Services/IOrganizationService.cs
+++ b/src/Core/AdminConsole/Services/IOrganizationService.cs
@@ -25,7 +25,7 @@ public interface IOrganizationService
     /// </summary>
     /// <returns>A tuple containing the new organization, the initial organizationUser (if any) and the default collection (if any)</returns>
 #nullable enable
-    Task<(Organization organization, OrganizationUser? organizationUser, Collection? defaultCollection)> SignUpAsync(OrganizationSignup organizationSignup, bool provider = false);
+    Task<(Organization organization, OrganizationUser? organizationUser, Collection? defaultCollection)> SignUpAsync(OrganizationSignup organizationSignup);
 
     Task<(Organization organization, OrganizationUser organizationUser, Collection defaultCollection)> SignupClientAsync(OrganizationSignup signup);
 #nullable disable
diff --git a/src/Core/AdminConsole/Services/Implementations/OrganizationService.cs b/src/Core/AdminConsole/Services/Implementations/OrganizationService.cs
index e73217b7f5..3bf69cc077 100644
--- a/src/Core/AdminConsole/Services/Implementations/OrganizationService.cs
+++ b/src/Core/AdminConsole/Services/Implementations/OrganizationService.cs
@@ -15,6 +15,7 @@ using Bit.Core.Auth.Models.Business.Tokenables;
 using Bit.Core.Auth.Repositories;
 using Bit.Core.Auth.UserFeatures.TwoFactorAuth.Interfaces;
 using Bit.Core.Billing.Enums;
+using Bit.Core.Billing.Models.Sales;
 using Bit.Core.Billing.Services;
 using Bit.Core.Context;
 using Bit.Core.Entities;
@@ -502,8 +503,7 @@ public class OrganizationService : IOrganizationService
     /// <summary>
     /// Create a new organization in a cloud environment
     /// </summary>
-    public async Task<(Organization organization, OrganizationUser organizationUser, Collection defaultCollection)> SignUpAsync(OrganizationSignup signup,
-        bool provider = false)
+    public async Task<(Organization organization, OrganizationUser organizationUser, Collection defaultCollection)> SignUpAsync(OrganizationSignup signup)
     {
         var plan = StaticStore.GetPlan(signup.Plan);
 
@@ -511,7 +511,7 @@ public class OrganizationService : IOrganizationService
 
         if (signup.UseSecretsManager)
         {
-            if (provider)
+            if (signup.IsFromProvider)
             {
                 throw new BadRequestException(
                     "Organizations with a Managed Service Provider do not support Secrets Manager.");
@@ -519,7 +519,7 @@ public class OrganizationService : IOrganizationService
             ValidateSecretsManagerPlan(plan, signup);
         }
 
-        if (!provider)
+        if (!signup.IsFromProvider)
         {
             await ValidateSignUpPoliciesAsync(signup.Owner.Id);
         }
@@ -570,7 +570,7 @@ public class OrganizationService : IOrganizationService
                                              signup.AdditionalServiceAccounts.GetValueOrDefault();
         }
 
-        if (plan.Type == PlanType.Free && !provider)
+        if (plan.Type == PlanType.Free && !signup.IsFromProvider)
         {
             var adminCount =
                 await _organizationUserRepository.GetCountByFreeOrganizationAdminUserAsync(signup.Owner.Id);
@@ -585,20 +585,19 @@ public class OrganizationService : IOrganizationService
 
             if (deprecateStripeSourcesAPI)
             {
-                var subscriptionPurchase = signup.ToSubscriptionPurchase(provider);
-
-                await _organizationBillingService.PurchaseSubscription(organization, subscriptionPurchase);
+                var sale = OrganizationSale.From(organization, signup);
+                await _organizationBillingService.Finalize(sale);
             }
             else
             {
                 await _paymentService.PurchaseOrganizationAsync(organization, signup.PaymentMethodType.Value,
                     signup.PaymentToken, plan, signup.AdditionalStorageGb, signup.AdditionalSeats,
-                    signup.PremiumAccessAddon, signup.TaxInfo, provider, signup.AdditionalSmSeats.GetValueOrDefault(),
+                    signup.PremiumAccessAddon, signup.TaxInfo, signup.IsFromProvider, signup.AdditionalSmSeats.GetValueOrDefault(),
                     signup.AdditionalServiceAccounts.GetValueOrDefault(), signup.IsFromSecretsManagerTrial);
             }
         }
 
-        var ownerId = provider ? default : signup.Owner.Id;
+        var ownerId = signup.IsFromProvider ? default : signup.Owner.Id;
         var returnValue = await SignUpAsync(organization, ownerId, signup.OwnerKey, signup.CollectionName, true);
         await _referenceEventService.RaiseEventAsync(
             new ReferenceEvent(ReferenceEventType.Signup, organization, _currentContext)
diff --git a/src/Core/Billing/Models/OrganizationSubscriptionPurchase.cs b/src/Core/Billing/Models/OrganizationSubscriptionPurchase.cs
deleted file mode 100644
index 8a97b9dd5c..0000000000
--- a/src/Core/Billing/Models/OrganizationSubscriptionPurchase.cs
+++ /dev/null
@@ -1,27 +0,0 @@
-using Bit.Core.Billing.Enums;
-
-namespace Bit.Core.Billing.Models;
-
-public record OrganizationSubscriptionPurchase(
-    OrganizationSubscriptionPurchaseMetadata Metadata,
-    OrganizationPasswordManagerSubscriptionPurchase PasswordManagerSubscription,
-    TokenizedPaymentSource PaymentSource,
-    PlanType PlanType,
-    OrganizationSecretsManagerSubscriptionPurchase SecretsManagerSubscription,
-    TaxInformation TaxInformation);
-
-public record OrganizationPasswordManagerSubscriptionPurchase(
-    int Storage,
-    bool PremiumAccess,
-    int Seats);
-
-public record OrganizationSecretsManagerSubscriptionPurchase(
-    int Seats,
-    int ServiceAccounts);
-
-public record OrganizationSubscriptionPurchaseMetadata(
-    bool FromProvider,
-    bool FromSecretsManagerStandalone)
-{
-    public static OrganizationSubscriptionPurchaseMetadata Default => new(false, false);
-}
diff --git a/src/Core/Billing/Models/Sales/CustomerSetup.cs b/src/Core/Billing/Models/Sales/CustomerSetup.cs
new file mode 100644
index 0000000000..47fd5621dd
--- /dev/null
+++ b/src/Core/Billing/Models/Sales/CustomerSetup.cs
@@ -0,0 +1,10 @@
+namespace Bit.Core.Billing.Models.Sales;
+
+#nullable enable
+
+public class CustomerSetup
+{
+    public required TokenizedPaymentSource TokenizedPaymentSource { get; set; }
+    public required TaxInformation TaxInformation { get; set; }
+    public string? Coupon { get; set; }
+}
diff --git a/src/Core/Billing/Models/Sales/OrganizationSale.cs b/src/Core/Billing/Models/Sales/OrganizationSale.cs
new file mode 100644
index 0000000000..4d471a84dc
--- /dev/null
+++ b/src/Core/Billing/Models/Sales/OrganizationSale.cs
@@ -0,0 +1,104 @@
+using Bit.Core.AdminConsole.Entities;
+using Bit.Core.Billing.Constants;
+using Bit.Core.Models.Business;
+
+namespace Bit.Core.Billing.Models.Sales;
+
+#nullable enable
+
+public class OrganizationSale
+{
+    private OrganizationSale() { }
+
+    public void Deconstruct(
+        out Organization organization,
+        out CustomerSetup? customerSetup,
+        out SubscriptionSetup subscriptionSetup)
+    {
+        organization = Organization;
+        customerSetup = CustomerSetup;
+        subscriptionSetup = SubscriptionSetup;
+    }
+
+    public required Organization Organization { get; init; }
+    public CustomerSetup? CustomerSetup { get; init; }
+    public required SubscriptionSetup SubscriptionSetup { get; init; }
+
+    public static OrganizationSale From(
+        Organization organization,
+        OrganizationSignup signup) => new()
+        {
+            Organization = organization,
+            CustomerSetup = string.IsNullOrEmpty(organization.GatewayCustomerId) ? GetCustomerSetup(signup) : null,
+            SubscriptionSetup = GetSubscriptionSetup(signup)
+        };
+
+    public static OrganizationSale From(
+        Organization organization,
+        OrganizationUpgrade upgrade) => new()
+        {
+            Organization = organization,
+            SubscriptionSetup = GetSubscriptionSetup(upgrade)
+        };
+
+    private static CustomerSetup? GetCustomerSetup(OrganizationSignup signup)
+    {
+        if (!signup.PaymentMethodType.HasValue)
+        {
+            return null;
+        }
+
+        var tokenizedPaymentSource = new TokenizedPaymentSource(
+            signup.PaymentMethodType!.Value,
+            signup.PaymentToken);
+
+        var taxInformation = new TaxInformation(
+            signup.TaxInfo.BillingAddressCountry,
+            signup.TaxInfo.BillingAddressPostalCode,
+            signup.TaxInfo.TaxIdNumber,
+            signup.TaxInfo.BillingAddressLine1,
+            signup.TaxInfo.BillingAddressLine2,
+            signup.TaxInfo.BillingAddressCity,
+            signup.TaxInfo.BillingAddressState);
+
+        var coupon = signup.IsFromProvider
+            ? StripeConstants.CouponIDs.MSPDiscount35
+            : signup.IsFromSecretsManagerTrial
+                ? StripeConstants.CouponIDs.SecretsManagerStandalone
+                : null;
+
+        return new CustomerSetup
+        {
+            TokenizedPaymentSource = tokenizedPaymentSource,
+            TaxInformation = taxInformation,
+            Coupon = coupon
+        };
+    }
+
+    private static SubscriptionSetup GetSubscriptionSetup(OrganizationUpgrade upgrade)
+    {
+        var plan = Core.Utilities.StaticStore.GetPlan(upgrade.Plan);
+
+        var passwordManagerOptions = new SubscriptionSetup.PasswordManager
+        {
+            Seats = upgrade.AdditionalSeats,
+            Storage = upgrade.AdditionalStorageGb,
+            PremiumAccess = upgrade.PremiumAccessAddon
+        };
+
+        var secretsManagerOptions = upgrade.UseSecretsManager
+            ? new SubscriptionSetup.SecretsManager
+            {
+                Seats = upgrade.AdditionalSmSeats ?? 0,
+                ServiceAccounts = upgrade.AdditionalServiceAccounts
+            }
+            : null;
+
+        return new SubscriptionSetup
+        {
+            Plan = plan,
+            PasswordManagerOptions = passwordManagerOptions,
+            SecretsManagerOptions = secretsManagerOptions
+        };
+    }
+}
diff --git a/src/Core/Billing/Models/Sales/SubscriptionSetup.cs b/src/Core/Billing/Models/Sales/SubscriptionSetup.cs
new file mode 100644
index 0000000000..cd87b2bb1c
--- /dev/null
+++ b/src/Core/Billing/Models/Sales/SubscriptionSetup.cs
@@ -0,0 +1,25 @@
+using Bit.Core.Models.StaticStore;
+
+namespace Bit.Core.Billing.Models.Sales;
+
+#nullable enable
+
+public class SubscriptionSetup
+{
+    public required Plan Plan { get; set; }
+    public required PasswordManager PasswordManagerOptions { get; set; }
+    public SecretsManager? SecretsManagerOptions { get; set; }
+
+    public class PasswordManager
+    {
+        public required int Seats { get; set; }
+        public short? Storage { get; set; }
+        public bool? PremiumAccess { get; set; }
+    }
+
+    public class SecretsManager
+    {
+        public required int Seats { get; set; }
+        public int? ServiceAccounts { get; set; }
+    }
+}
diff --git a/src/Core/Billing/Models/StaticStore/Plan.cs b/src/Core/Billing/Models/StaticStore/Plan.cs
index 04488c206d..15a618cca0 100644
--- a/src/Core/Billing/Models/StaticStore/Plan.cs
+++ b/src/Core/Billing/Models/StaticStore/Plan.cs
@@ -34,6 +34,9 @@ public abstract record Plan
     public SecretsManagerPlanFeatures SecretsManager { get; protected init; }
     public bool SupportsSecretsManager => SecretsManager != null;
 
+    public bool HasNonSeatBasedPasswordManagerPlan() =>
+        PasswordManager is { StripePlanId: not null and not "", StripeSeatPlanId: null or "" };
+
     public record SecretsManagerPlanFeatures
     {
         // Service accounts
diff --git a/src/Core/Billing/Models/TaxInformation.cs b/src/Core/Billing/Models/TaxInformation.cs
index a2e6e187f2..7c03b90f65 100644
--- a/src/Core/Billing/Models/TaxInformation.cs
+++ b/src/Core/Billing/Models/TaxInformation.cs
@@ -1,4 +1,6 @@
-namespace Bit.Core.Billing.Models;
+using Stripe;
+
+namespace Bit.Core.Billing.Models;
 
 public record TaxInformation(
     string Country,
@@ -9,6 +11,25 @@ public record TaxInformation(
     string City,
     string State)
 {
+    public (AddressOptions, List<CustomerTaxIdDataOptions>) GetStripeOptions()
+    {
+        var address = new AddressOptions
+        {
+            Country = Country,
+            PostalCode = PostalCode,
+            Line1 = Line1,
+            Line2 = Line2,
+            City = City,
+            State = State
+        };
+
+        var customerTaxIdDataOptionsList = !string.IsNullOrEmpty(TaxId)
+            ? new List<CustomerTaxIdDataOptions> { new() { Type = GetTaxIdType(), Value = TaxId } }
+            : null;
+
+        return (address, customerTaxIdDataOptionsList);
+    }
+
     public string GetTaxIdType()
     {
         if (string.IsNullOrEmpty(Country) || string.IsNullOrEmpty(TaxId))
diff --git a/src/Core/Billing/Services/IOrganizationBillingService.cs b/src/Core/Billing/Services/IOrganizationBillingService.cs
index 469d638354..c4d02db7fb 100644
--- a/src/Core/Billing/Services/IOrganizationBillingService.cs
+++ b/src/Core/Billing/Services/IOrganizationBillingService.cs
@@ -1,10 +1,29 @@
 using Bit.Core.AdminConsole.Entities;
 using Bit.Core.Billing.Models;
+using Bit.Core.Billing.Models.Sales;
 
 namespace Bit.Core.Billing.Services;
 
 public interface IOrganizationBillingService
 {
+    /// <summary>
+    /// <para>Establishes the billing configuration for a Bitwarden <see cref="Organization"/> using the provided <paramref name="sale"/>.</para>
+    /// <para>
+    /// The method first checks to see if the
+    /// provided <see cref="OrganizationSale.Organization"/> already has a Stripe <see cref="Stripe.Customer"/> using the <see cref="Organization.GatewayCustomerId"/>.
+    /// If it doesn't, the method creates one using the <paramref name="sale"/>'s <see cref="OrganizationSale.CustomerSetup"/>. The method then creates a Stripe <see cref="Stripe.Subscription"/>
+    /// for the created or existing customer using the provided <see cref="OrganizationSale.SubscriptionSetup"/>.
+    /// </para>
+    /// </summary>
+    /// <param name="sale">The purchase details necessary to establish the Stripe entities responsible for billing the organization.</param>
+    /// <example>
+    /// <code>
+    /// var sale = OrganizationSale.From(organization, organizationSignup);
+    /// await organizationBillingService.Finalize(sale);
+    /// </code>
+    /// </example>
+    Task Finalize(OrganizationSale sale);
+
     /// <summary>
     /// Retrieve metadata about the organization represented bsy the provided <paramref name="organizationId"/>.
     /// </summary>
@@ -13,11 +32,15 @@ public interface IOrganizationBillingService
     Task<OrganizationMetadata> GetMetadata(Guid organizationId);
 
     /// <summary>
-    /// Purchase a subscription for the provided <paramref name="organization"/> using the provided <paramref name="organizationSubscriptionPurchase"/>.
-    /// If successful, a Stripe <see cref="Stripe.Customer"/> and <see cref="Stripe.Subscription"/> will be created for the organization and the
-    /// organization will be enabled.
+    /// Updates the provided <paramref name="organization"/>'s payment source and tax information.
+    /// If the <paramref name="organization"/> does not have a Stripe <see cref="Stripe.Customer"/>, this method will create one using the provided
+    /// <paramref name="tokenizedPaymentSource"/> and <paramref name="taxInformation"/>.
     /// </summary>
-    /// <param name="organization">The organization to purchase a subscription for.</param>
-    /// <param name="organizationSubscriptionPurchase">The purchase information for the organization's subscription.</param>
-    Task PurchaseSubscription(Organization organization, OrganizationSubscriptionPurchase organizationSubscriptionPurchase);
+    /// <param name="organization">The <paramref name="organization"/> to update the payment source and tax information for.</param>
+    /// <param name="tokenizedPaymentSource">The tokenized payment source (ex. Credit Card) to attach to the <paramref name="organization"/>.</param>
+    /// <param name="taxInformation">The <paramref name="organization"/>'s updated tax information.</param>
+    Task UpdatePaymentMethod(
+        Organization organization,
+        TokenizedPaymentSource tokenizedPaymentSource,
+        TaxInformation taxInformation);
 }
diff --git a/src/Core/Billing/Services/Implementations/OrganizationBillingService.cs b/src/Core/Billing/Services/Implementations/OrganizationBillingService.cs
index af65ce427d..9b76a04f15 100644
--- a/src/Core/Billing/Services/Implementations/OrganizationBillingService.cs
+++ b/src/Core/Billing/Services/Implementations/OrganizationBillingService.cs
@@ -1,8 +1,8 @@
 using Bit.Core.AdminConsole.Entities;
 using Bit.Core.Billing.Caches;
 using Bit.Core.Billing.Constants;
-using Bit.Core.Billing.Enums;
 using Bit.Core.Billing.Models;
+using Bit.Core.Billing.Models.Sales;
 using Bit.Core.Enums;
 using Bit.Core.Exceptions;
 using Bit.Core.Repositories;
@@ -28,6 +28,31 @@ public class OrganizationBillingService(
     IStripeAdapter stripeAdapter,
     ISubscriberService subscriberService) : IOrganizationBillingService
 {
+    public async Task Finalize(OrganizationSale sale)
+    {
+        var (organization, customerSetup, subscriptionSetup) = sale;
+
+        List<string> expand = ["tax"];
+
+        var customer = customerSetup != null
+            ? await CreateCustomerAsync(organization, customerSetup, expand)
+            : await subscriberService.GetCustomerOrThrow(organization, new CustomerGetOptions { Expand = expand });
+
+        var subscription = await CreateSubscriptionAsync(organization.Id, customer, subscriptionSetup);
+
+        if (subscription.Status is StripeConstants.SubscriptionStatus.Trialing or StripeConstants.SubscriptionStatus.Active)
+        {
+            organization.Enabled = true;
+            organization.ExpirationDate = subscription.CurrentPeriodEnd;
+        }
+
+        organization.Gateway = GatewayType.Stripe;
+        organization.GatewayCustomerId = customer.Id;
+        organization.GatewaySubscriptionId = subscription.Id;
+
+        await organizationRepository.ReplaceAsync(organization);
+    }
+
     public async Task<OrganizationMetadata> GetMetadata(Guid organizationId)
     {
         var organization = await organizationRepository.GetByIdAsync(organizationId);
@@ -54,97 +79,72 @@ public class OrganizationBillingService(
         return new OrganizationMetadata(isOnSecretsManagerStandalone);
     }
 
-    public async Task PurchaseSubscription(
+    public async Task UpdatePaymentMethod(
         Organization organization,
-        OrganizationSubscriptionPurchase organizationSubscriptionPurchase)
+        TokenizedPaymentSource tokenizedPaymentSource,
+        TaxInformation taxInformation)
     {
-        ArgumentNullException.ThrowIfNull(organization);
-        ArgumentNullException.ThrowIfNull(organizationSubscriptionPurchase);
+        if (string.IsNullOrEmpty(organization.GatewayCustomerId))
+        {
+            var customer = await CreateCustomerAsync(organization,
+                new CustomerSetup
+                {
+                    TokenizedPaymentSource = tokenizedPaymentSource,
+                    TaxInformation = taxInformation,
+                });
 
-        var (
-            metadata,
-            passwordManager,
-            paymentSource,
-            planType,
-            secretsManager,
-            taxInformation) = organizationSubscriptionPurchase;
+            organization.Gateway = GatewayType.Stripe;
+            organization.GatewayCustomerId = customer.Id;
 
-        var customer = await CreateCustomerAsync(organization, metadata, paymentSource, taxInformation);
-
-        var subscription =
-            await CreateSubscriptionAsync(customer, organization.Id, passwordManager, planType, secretsManager);
-
-        organization.Enabled = true;
-        organization.ExpirationDate = subscription.CurrentPeriodEnd;
-        organization.Gateway = GatewayType.Stripe;
-        organization.GatewayCustomerId = customer.Id;
-        organization.GatewaySubscriptionId = subscription.Id;
-
-        await organizationRepository.ReplaceAsync(organization);
+            await organizationRepository.ReplaceAsync(organization);
+        }
+        else
+        {
+            await subscriberService.UpdatePaymentSource(organization, tokenizedPaymentSource);
+            await subscriberService.UpdateTaxInformation(organization, taxInformation);
+        }
     }
 
     #region Utilities
 
     private async Task<Customer> CreateCustomerAsync(
         Organization organization,
-        OrganizationSubscriptionPurchaseMetadata metadata,
-        TokenizedPaymentSource paymentSource,
-        TaxInformation taxInformation)
+        CustomerSetup customerSetup,
+        List<string> expand = null)
     {
-        if (paymentSource == null)
+        if (customerSetup.TokenizedPaymentSource is not
+            {
+                Type: PaymentMethodType.BankAccount or PaymentMethodType.Card or PaymentMethodType.PayPal,
+                Token: not null and not ""
+            })
         {
             logger.LogError(
-                "Cannot create customer for organization ({OrganizationID}) without a payment source",
+                "Cannot create customer for organization ({OrganizationID}) without a valid payment source",
                 organization.Id);
 
             throw new BillingException();
         }
 
-        if (taxInformation is not { Country: not null, PostalCode: not null })
+        if (customerSetup.TaxInformation is not { Country: not null and not "", PostalCode: not null and not "" })
         {
             logger.LogError(
-                "Cannot create customer for organization ({OrganizationID}) without both a country and postal code",
+                "Cannot create customer for organization ({OrganizationID}) without valid tax information",
                 organization.Id);
 
             throw new BillingException();
         }
 
-        var (
-            country,
-            postalCode,
-            taxId,
-            line1,
-            line2,
-            city,
-            state) = taxInformation;
-
-        var address = new AddressOptions
-        {
-            Country = country,
-            PostalCode = postalCode,
-            City = city,
-            Line1 = line1,
-            Line2 = line2,
-            State = state
-        };
-
-        var (fromProvider, fromSecretsManagerStandalone) = metadata ?? OrganizationSubscriptionPurchaseMetadata.Default;
-
-        var coupon = fromProvider
-            ? StripeConstants.CouponIDs.MSPDiscount35
-            : fromSecretsManagerStandalone
-                ? StripeConstants.CouponIDs.SecretsManagerStandalone
-                : null;
+        var (address, taxIdData) = customerSetup.TaxInformation.GetStripeOptions();
 
         var organizationDisplayName = organization.DisplayName();
 
         var customerCreateOptions = new CustomerCreateOptions
         {
             Address = address,
-            Coupon = coupon,
+            Coupon = customerSetup.Coupon,
             Description = organization.DisplayBusinessName(),
             Email = organization.BillingEmail,
-            Expand = ["tax"],
+            Expand = expand,
             InvoiceSettings = new CustomerInvoiceSettingsOptions
             {
                 CustomFields = [
@@ -164,21 +164,10 @@ public class OrganizationBillingService(
             {
                 ValidateLocation = StripeConstants.ValidateTaxLocationTiming.Immediately
             },
-            TaxIdData = !string.IsNullOrEmpty(taxId)
-                ? [new CustomerTaxIdDataOptions { Type = taxInformation.GetTaxIdType(), Value = taxId }]
-                : null
+            TaxIdData = taxIdData
         };
 
-        var (type, token) = paymentSource;
-
-        if (string.IsNullOrEmpty(token))
-        {
-            logger.LogError(
-                "Cannot create customer for organization ({OrganizationID}) without a payment source token",
-                organization.Id);
-
-            throw new BillingException();
-        }
+        var (type, token) = customerSetup.TokenizedPaymentSource;
 
         var braintreeCustomerId = "";
 
@@ -270,31 +259,30 @@ public class OrganizationBillingService(
     }
 
     private async Task<Subscription> CreateSubscriptionAsync(
-        Customer customer,
         Guid organizationId,
-        OrganizationPasswordManagerSubscriptionPurchase passwordManager,
-        PlanType planType,
-        OrganizationSecretsManagerSubscriptionPurchase secretsManager)
+        Customer customer,
+        SubscriptionSetup subscriptionSetup)
     {
-        var plan = StaticStore.GetPlan(planType);
+        var plan = subscriptionSetup.Plan;
 
-        if (passwordManager == null)
-        {
-            logger.LogError("Cannot create subscription for organization ({OrganizationID}) without password manager purchase information", organizationId);
-
-            throw new BillingException();
-        }
+        var passwordManagerOptions = subscriptionSetup.PasswordManagerOptions;
 
         var subscriptionItemOptionsList = new List<SubscriptionItemOptions>
         {
-            new ()
-            {
-                Price = plan.PasswordManager.StripeSeatPlanId,
-                Quantity = passwordManager.Seats
-            }
+            plan.HasNonSeatBasedPasswordManagerPlan()
+                ? new SubscriptionItemOptions
+                {
+                    Price = plan.PasswordManager.StripePlanId,
+                    Quantity = 1
+                }
+                : new SubscriptionItemOptions
+                {
+                    Price = plan.PasswordManager.StripeSeatPlanId,
+                    Quantity = passwordManagerOptions.Seats
+                }
         };
 
-        if (passwordManager.PremiumAccess)
+        if (passwordManagerOptions.PremiumAccess is true)
         {
             subscriptionItemOptionsList.Add(new SubscriptionItemOptions
             {
@@ -303,29 +291,31 @@ public class OrganizationBillingService(
             });
         }
 
-        if (passwordManager.Storage > 0)
+        if (passwordManagerOptions.Storage is > 0)
         {
             subscriptionItemOptionsList.Add(new SubscriptionItemOptions
             {
                 Price = plan.PasswordManager.StripeStoragePlanId,
-                Quantity = passwordManager.Storage
+                Quantity = passwordManagerOptions.Storage
             });
         }
 
-        if (secretsManager != null)
+        var secretsManagerOptions = subscriptionSetup.SecretsManagerOptions;
+
+        if (secretsManagerOptions != null)
         {
             subscriptionItemOptionsList.Add(new SubscriptionItemOptions
             {
                 Price = plan.SecretsManager.StripeSeatPlanId,
-                Quantity = secretsManager.Seats
+                Quantity = secretsManagerOptions.Seats
             });
 
-            if (secretsManager.ServiceAccounts > 0)
+            if (secretsManagerOptions.ServiceAccounts is > 0)
             {
                 subscriptionItemOptionsList.Add(new SubscriptionItemOptions
                 {
                     Price = plan.SecretsManager.StripeServiceAccountPlanId,
-                    Quantity = secretsManager.ServiceAccounts
+                    Quantity = secretsManagerOptions.ServiceAccounts
                 });
             }
         }
@@ -347,15 +337,7 @@ public class OrganizationBillingService(
             TrialPeriodDays = plan.TrialPeriodDays,
         };
 
-        try
-        {
-            return await stripeAdapter.SubscriptionCreateAsync(subscriptionCreateOptions);
-        }
-        catch
-        {
-            await stripeAdapter.CustomerDeleteAsync(customer.Id);
-            throw;
-        }
+        return await stripeAdapter.SubscriptionCreateAsync(subscriptionCreateOptions);
     }
 
     private static bool IsOnSecretsManagerStandalone(
diff --git a/src/Core/Billing/Services/Implementations/SubscriberService.cs b/src/Core/Billing/Services/Implementations/SubscriberService.cs
index c44bb3f3b9..33eb8e7e8a 100644
--- a/src/Core/Billing/Services/Implementations/SubscriberService.cs
+++ b/src/Core/Billing/Services/Implementations/SubscriberService.cs
@@ -1,4 +1,5 @@
 using Bit.Core.Billing.Caches;
+using Bit.Core.Billing.Constants;
 using Bit.Core.Billing.Models;
 using Bit.Core.Entities;
 using Bit.Core.Enums;
@@ -585,7 +586,7 @@ public class SubscriberService(
 
         var customer = await GetCustomerOrThrow(subscriber, new CustomerGetOptions
         {
-            Expand = ["tax_ids"]
+            Expand = ["subscriptions", "tax", "tax_ids"]
         });
 
         await stripeAdapter.CustomerUpdateAsync(customer.Id, new CustomerUpdateOptions
@@ -622,6 +623,23 @@ public class SubscriberService(
                 });
             }
         }
+
+        if (SubscriberIsEligibleForAutomaticTax(subscriber, customer))
+        {
+            await stripeAdapter.SubscriptionUpdateAsync(subscriber.GatewaySubscriptionId,
+                new SubscriptionUpdateOptions
+                {
+                    AutomaticTax = new SubscriptionAutomaticTaxOptions { Enabled = true },
+                    DefaultTaxRates = []
+                });
+        }
+
+        return;
+
+        bool SubscriberIsEligibleForAutomaticTax(ISubscriber localSubscriber, Customer localCustomer)
+            => !string.IsNullOrEmpty(localSubscriber.GatewaySubscriptionId) &&
+               (localCustomer.Subscriptions?.Any(sub => sub.Id == localSubscriber.GatewaySubscriptionId && !sub.AutomaticTax.Enabled) ?? false) &&
+               localCustomer.Tax?.AutomaticTax == StripeConstants.AutomaticTaxStatus.Supported;
     }
 
     public async Task VerifyBankAccount(
diff --git a/src/Core/Models/Business/OrganizationSignup.cs b/src/Core/Models/Business/OrganizationSignup.cs
index a5155da755..b5ac69e73f 100644
--- a/src/Core/Models/Business/OrganizationSignup.cs
+++ b/src/Core/Models/Business/OrganizationSignup.cs
@@ -1,5 +1,4 @@
-using Bit.Core.Billing.Models;
-using Bit.Core.Entities;
+using Bit.Core.Entities;
 using Bit.Core.Enums;
 
 namespace Bit.Core.Models.Business;
@@ -15,42 +14,6 @@ public class OrganizationSignup : OrganizationUpgrade
     public string PaymentToken { get; set; }
     public int? MaxAutoscaleSeats { get; set; } = null;
     public string InitiationPath { get; set; }
-
-    public OrganizationSubscriptionPurchase ToSubscriptionPurchase(bool fromProvider = false)
-    {
-        if (!PaymentMethodType.HasValue)
-        {
-            return null;
-        }
-
-        var metadata = new OrganizationSubscriptionPurchaseMetadata(fromProvider, IsFromSecretsManagerTrial);
-
-        var passwordManager = new OrganizationPasswordManagerSubscriptionPurchase(
-            AdditionalStorageGb,
-            PremiumAccessAddon,
-            AdditionalSeats);
-
-        var paymentSource = new TokenizedPaymentSource(PaymentMethodType.Value, PaymentToken);
-
-        var secretsManager = new OrganizationSecretsManagerSubscriptionPurchase(
-            AdditionalSmSeats ?? 0,
-            AdditionalServiceAccounts ?? 0);
-
-        var taxInformation = new TaxInformation(
-            TaxInfo.BillingAddressCountry,
-            TaxInfo.BillingAddressPostalCode,
-            TaxInfo.TaxIdNumber,
-            TaxInfo.BillingAddressLine1,
-            TaxInfo.BillingAddressLine2,
-            TaxInfo.BillingAddressCity,
-            TaxInfo.BillingAddressState);
-
-        return new OrganizationSubscriptionPurchase(
-            metadata,
-            passwordManager,
-            paymentSource,
-            Plan,
-            UseSecretsManager ? secretsManager : null,
-            taxInformation);
-    }
+    public bool IsFromSecretsManagerTrial { get; set; }
+    public bool IsFromProvider { get; set; }
 }
diff --git a/src/Core/Models/Business/OrganizationUpgrade.cs b/src/Core/Models/Business/OrganizationUpgrade.cs
index 4928ecf654..1dd2650799 100644
--- a/src/Core/Models/Business/OrganizationUpgrade.cs
+++ b/src/Core/Models/Business/OrganizationUpgrade.cs
@@ -15,5 +15,4 @@ 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/OrganizationFeatures/OrganizationSubscriptions/UpgradeOrganizationPlanCommand.cs b/src/Core/OrganizationFeatures/OrganizationSubscriptions/UpgradeOrganizationPlanCommand.cs
index cf234ef609..33dd388333 100644
--- a/src/Core/OrganizationFeatures/OrganizationSubscriptions/UpgradeOrganizationPlanCommand.cs
+++ b/src/Core/OrganizationFeatures/OrganizationSubscriptions/UpgradeOrganizationPlanCommand.cs
@@ -5,6 +5,8 @@ using Bit.Core.AdminConsole.Repositories;
 using Bit.Core.Auth.Enums;
 using Bit.Core.Auth.Repositories;
 using Bit.Core.Billing.Enums;
+using Bit.Core.Billing.Models.Sales;
+using Bit.Core.Billing.Services;
 using Bit.Core.Context;
 using Bit.Core.Enums;
 using Bit.Core.Exceptions;
@@ -34,6 +36,8 @@ public class UpgradeOrganizationPlanCommand : IUpgradeOrganizationPlanCommand
     private readonly IServiceAccountRepository _serviceAccountRepository;
     private readonly IOrganizationRepository _organizationRepository;
     private readonly IOrganizationService _organizationService;
+    private readonly IFeatureService _featureService;
+    private readonly IOrganizationBillingService _organizationBillingService;
 
     public UpgradeOrganizationPlanCommand(
         IOrganizationUserRepository organizationUserRepository,
@@ -47,7 +51,9 @@ public class UpgradeOrganizationPlanCommand : IUpgradeOrganizationPlanCommand
         ICurrentContext currentContext,
         IServiceAccountRepository serviceAccountRepository,
         IOrganizationRepository organizationRepository,
-        IOrganizationService organizationService)
+        IOrganizationService organizationService,
+        IFeatureService featureService,
+        IOrganizationBillingService organizationBillingService)
     {
         _organizationUserRepository = organizationUserRepository;
         _collectionRepository = collectionRepository;
@@ -61,6 +67,8 @@ public class UpgradeOrganizationPlanCommand : IUpgradeOrganizationPlanCommand
         _serviceAccountRepository = serviceAccountRepository;
         _organizationRepository = organizationRepository;
         _organizationService = organizationService;
+        _featureService = featureService;
+        _organizationBillingService = organizationBillingService;
     }
 
     public async Task<Tuple<bool, string>> UpgradePlanAsync(Guid organizationId, OrganizationUpgrade upgrade)
@@ -216,9 +224,17 @@ public class UpgradeOrganizationPlanCommand : IUpgradeOrganizationPlanCommand
 
         if (string.IsNullOrWhiteSpace(organization.GatewaySubscriptionId))
         {
-            paymentIntentClientSecret = await _paymentService.UpgradeFreeOrganizationAsync(organization,
-                newPlan, upgrade);
-            success = string.IsNullOrWhiteSpace(paymentIntentClientSecret);
+            if (_featureService.IsEnabled(FeatureFlagKeys.AC2476_DeprecateStripeSourcesAPI))
+            {
+                var sale = OrganizationSale.From(organization, upgrade);
+                await _organizationBillingService.Finalize(sale);
+            }
+            else
+            {
+                paymentIntentClientSecret = await _paymentService.UpgradeFreeOrganizationAsync(organization,
+                    newPlan, upgrade);
+                success = string.IsNullOrWhiteSpace(paymentIntentClientSecret);
+            }
         }
         else
         {
diff --git a/test/Core.Test/AdminConsole/Services/OrganizationServiceTests.cs b/test/Core.Test/AdminConsole/Services/OrganizationServiceTests.cs
index 5f0038a21a..4bef18f555 100644
--- a/test/Core.Test/AdminConsole/Services/OrganizationServiceTests.cs
+++ b/test/Core.Test/AdminConsole/Services/OrganizationServiceTests.cs
@@ -354,8 +354,9 @@ public class OrganizationServiceTests
         signup.AdditionalServiceAccounts = 20;
         signup.PaymentMethodType = PaymentMethodType.Card;
         signup.PremiumAccessAddon = false;
+        signup.IsFromProvider = true;
 
-        var exception = await Assert.ThrowsAsync<BadRequestException>(() => sutProvider.Sut.SignUpAsync(signup, true));
+        var exception = await Assert.ThrowsAsync<BadRequestException>(() => sutProvider.Sut.SignUpAsync(signup));
         Assert.Contains("Organizations with a Managed Service Provider do not support Secrets Manager.", exception.Message);
     }