[PM-19147] Automatic Tax Improvements (#5545)

* Pm 19147 2 (#5544)

* Pm 19147 2 (#5544)

* Unit tests for tax strategies `GetUpdateOptions`

* Only allow automatic tax flag to be updated for complete subscription updates such as plan changes, not when upgrading additional storage, seats, etc

* unit tests for factory

* Fix build

* Automatic tax for tax estimation

* Fix stub

* Fix stub

* "customer.tax_ids" isn't expanded in some flows.

* Fix SubscriberServiceTests.cs

* BusinessUseAutomaticTaxStrategy > SetUpdateOptions tests

* Fix ProviderBillingServiceTests.cs

src/Billing/Services/Implementations/UpcomingInvoiceHandler.cs

@@ -1,8 +1,11 @@
-using Bit.Core.AdminConsole.Repositories;
+using Bit.Core;
+using Bit.Core.AdminConsole.Repositories;
 using Bit.Core.Billing.Constants;
 using Bit.Core.Billing.Enums;
 using Bit.Core.Billing.Extensions;
 using Bit.Core.Billing.Pricing;
+using Bit.Core.Billing.Services;
+using Bit.Core.Billing.Services.Contracts;
 using Bit.Core.OrganizationFeatures.OrganizationSponsorships.FamiliesForEnterprise.Interfaces;
 using Bit.Core.Repositories;
 using Bit.Core.Services;
@@ -12,6 +15,7 @@ using Event = Stripe.Event;
 namespace Bit.Billing.Services.Implementations;
 
 public class UpcomingInvoiceHandler(
+    IFeatureService featureService,
     ILogger<StripeEventProcessor> logger,
     IMailService mailService,
     IOrganizationRepository organizationRepository,
@@ -21,7 +25,8 @@ public class UpcomingInvoiceHandler(
     IStripeEventService stripeEventService,
     IStripeEventUtilityService stripeEventUtilityService,
     IUserRepository userRepository,
-    IValidateSponsorshipCommand validateSponsorshipCommand)
+    IValidateSponsorshipCommand validateSponsorshipCommand,
+    IAutomaticTaxFactory automaticTaxFactory)
     : IUpcomingInvoiceHandler
 {
     public async Task HandleAsync(Event parsedEvent)
@@ -136,6 +141,21 @@ public class UpcomingInvoiceHandler(
 
     private async Task TryEnableAutomaticTaxAsync(Subscription subscription)
     {
+        if (featureService.IsEnabled(FeatureFlagKeys.PM19147_AutomaticTaxImprovements))
+        {
+            var automaticTaxParameters = new AutomaticTaxFactoryParameters(subscription.Items.Select(x => x.Price.Id));
+            var automaticTaxStrategy = await automaticTaxFactory.CreateAsync(automaticTaxParameters);
+            var updateOptions = automaticTaxStrategy.GetUpdateOptions(subscription);
+
+            if (updateOptions == null)
+            {
+                return;
+            }
+
+            await stripeFacade.UpdateSubscription(subscription.Id, updateOptions);
+            return;
+        }
+
         if (subscription.AutomaticTax.Enabled ||
             !subscription.Customer.HasBillingLocation() ||
             await IsNonTaxableNonUSBusinessUseSubscription(subscription))

src/Core/Billing/Constants/StripeConstants.cs

@@ -47,6 +47,8 @@ public static class StripeConstants
     public static class MetadataKeys
     {
         public const string OrganizationId = "organizationId";
+        public const string ProviderId = "providerId";
+        public const string UserId = "userId";
     }
 
     public static class PaymentBehavior

src/Core/Billing/Extensions/CustomerExtensions.cs

@@ -21,7 +21,7 @@ public static class CustomerExtensions
     /// <param name="customer"></param>
     /// <returns></returns>
     public static bool HasTaxLocationVerified(this Customer customer) =>
-        customer?.Tax?.AutomaticTax == StripeConstants.AutomaticTaxStatus.Supported;
+        customer?.Tax?.AutomaticTax != StripeConstants.AutomaticTaxStatus.UnrecognizedLocation;
 
     public static decimal GetBillingBalance(this Customer customer)
     {

src/Core/Billing/Extensions/ServiceCollectionExtensions.cs

@@ -4,6 +4,7 @@ using Bit.Core.Billing.Licenses.Extensions;
 using Bit.Core.Billing.Pricing;
 using Bit.Core.Billing.Services;
 using Bit.Core.Billing.Services.Implementations;
+using Bit.Core.Billing.Services.Implementations.AutomaticTax;
 
 namespace Bit.Core.Billing.Extensions;
 
@@ -18,6 +19,9 @@ public static class ServiceCollectionExtensions
         services.AddTransient<IPremiumUserBillingService, PremiumUserBillingService>();
         services.AddTransient<ISetupIntentCache, SetupIntentDistributedCache>();
         services.AddTransient<ISubscriberService, SubscriberService>();
+        services.AddKeyedTransient<IAutomaticTaxStrategy, PersonalUseAutomaticTaxStrategy>(AutomaticTaxFactory.PersonalUse);
+        services.AddKeyedTransient<IAutomaticTaxStrategy, BusinessUseAutomaticTaxStrategy>(AutomaticTaxFactory.BusinessUse);
+        services.AddTransient<IAutomaticTaxFactory, AutomaticTaxFactory>();
         services.AddLicenseServices();
         services.AddPricingClient();
     }

src/Core/Billing/Extensions/SubscriptionCreateOptionsExtensions.cs

@@ -1,26 +0,0 @@
-using Stripe;
-
-namespace Bit.Core.Billing.Extensions;
-
-public static class SubscriptionCreateOptionsExtensions
-{
-    /// <summary>
-    /// Attempts to enable automatic tax for given new subscription options.
-    /// </summary>
-    /// <param name="options"></param>
-    /// <param name="customer">The existing customer.</param>
-    /// <returns>Returns true when successful, false when conditions are not met.</returns>
-    public static bool EnableAutomaticTax(this SubscriptionCreateOptions options, Customer customer)
-    {
-        // We might only need to check the automatic tax status.
-        if (!customer.HasTaxLocationVerified() && string.IsNullOrWhiteSpace(customer.Address?.Country))
-        {
-            return false;
-        }
-
-        options.DefaultTaxRates = [];
-        options.AutomaticTax = new SubscriptionAutomaticTaxOptions { Enabled = true };
-
-        return true;
-    }
-}

src/Core/Billing/Services/Contracts/AutomaticTaxFactoryParameters.cs

@@ -0,0 +1,30 @@
+#nullable enable
+using Bit.Core.Billing.Enums;
+using Bit.Core.Entities;
+
+namespace Bit.Core.Billing.Services.Contracts;
+
+public class AutomaticTaxFactoryParameters
+{
+    public AutomaticTaxFactoryParameters(PlanType planType)
+    {
+        PlanType = planType;
+    }
+
+    public AutomaticTaxFactoryParameters(ISubscriber subscriber, IEnumerable<string> prices)
+    {
+        Subscriber = subscriber;
+        Prices = prices;
+    }
+
+    public AutomaticTaxFactoryParameters(IEnumerable<string> prices)
+    {
+        Prices = prices;
+    }
+
+    public ISubscriber? Subscriber { get; init; }
+
+    public PlanType? PlanType { get; init; }
+
+    public IEnumerable<string>? Prices { get; init; }
+}

src/Core/Billing/Services/IAutomaticTaxFactory.cs

@@ -0,0 +1,11 @@
+using Bit.Core.Billing.Services.Contracts;
+
+namespace Bit.Core.Billing.Services;
+
+/// <summary>
+/// Responsible for defining the correct automatic tax strategy for either personal use of business use.
+/// </summary>
+public interface IAutomaticTaxFactory
+{
+    Task<IAutomaticTaxStrategy> CreateAsync(AutomaticTaxFactoryParameters parameters);
+}

src/Core/Billing/Services/IAutomaticTaxStrategy.cs

@@ -0,0 +1,33 @@
+#nullable enable
+using Stripe;
+
+namespace Bit.Core.Billing.Services;
+
+public interface IAutomaticTaxStrategy
+{
+    /// <summary>
+    ///
+    /// </summary>
+    /// <param name="subscription"></param>
+    /// <returns>
+    /// Returns <see cref="SubscriptionUpdateOptions" /> if changes are to be applied to the subscription, returns null
+    /// otherwise.
+    /// </returns>
+    SubscriptionUpdateOptions? GetUpdateOptions(Subscription subscription);
+
+    /// <summary>
+    /// Modifies an existing <see cref="SubscriptionCreateOptions" /> object with the automatic tax flag set correctly.
+    /// </summary>
+    /// <param name="options"></param>
+    /// <param name="customer"></param>
+    void SetCreateOptions(SubscriptionCreateOptions options, Customer customer);
+
+    /// <summary>
+    /// Modifies an existing <see cref="SubscriptionUpdateOptions" /> object with the automatic tax flag set correctly.
+    /// </summary>
+    /// <param name="options"></param>
+    /// <param name="subscription"></param>
+    void SetUpdateOptions(SubscriptionUpdateOptions options, Subscription subscription);
+
+    void SetInvoiceCreatePreviewOptions(InvoiceCreatePreviewOptions options);
+}

src/Core/Billing/Services/Implementations/AutomaticTax/AutomaticTaxFactory.cs

@@ -0,0 +1,50 @@
+#nullable enable
+using Bit.Core.Billing.Enums;
+using Bit.Core.Billing.Pricing;
+using Bit.Core.Billing.Services.Contracts;
+using Bit.Core.Entities;
+using Bit.Core.Services;
+
+namespace Bit.Core.Billing.Services.Implementations.AutomaticTax;
+
+public class AutomaticTaxFactory(
+    IFeatureService featureService,
+    IPricingClient pricingClient) : IAutomaticTaxFactory
+{
+    public const string BusinessUse = "business-use";
+    public const string PersonalUse = "personal-use";
+
+    private readonly Lazy<Task<IEnumerable<string>>> _personalUsePlansTask = new(async () =>
+    {
+        var plans = await Task.WhenAll(
+            pricingClient.GetPlanOrThrow(PlanType.FamiliesAnnually2019),
+            pricingClient.GetPlanOrThrow(PlanType.FamiliesAnnually));
+
+        return plans.Select(plan => plan.PasswordManager.StripePlanId);
+    });
+
+    public async Task<IAutomaticTaxStrategy> CreateAsync(AutomaticTaxFactoryParameters parameters)
+    {
+        if (parameters.Subscriber is User)
+        {
+            return new PersonalUseAutomaticTaxStrategy(featureService);
+        }
+
+        if (parameters.PlanType.HasValue)
+        {
+            var plan = await pricingClient.GetPlanOrThrow(parameters.PlanType.Value);
+            return plan.CanBeUsedByBusiness
+                ? new BusinessUseAutomaticTaxStrategy(featureService)
+                : new PersonalUseAutomaticTaxStrategy(featureService);
+        }
+
+        var personalUsePlans = await _personalUsePlansTask.Value;
+
+        if (parameters.Prices != null && parameters.Prices.Any(x => personalUsePlans.Any(y => y == x)))
+        {
+            return new PersonalUseAutomaticTaxStrategy(featureService);
+        }
+
+        return new BusinessUseAutomaticTaxStrategy(featureService);
+    }
+}

src/Core/Billing/Services/Implementations/AutomaticTax/BusinessUseAutomaticTaxStrategy.cs

@@ -0,0 +1,96 @@
+#nullable enable
+using Bit.Core.Billing.Extensions;
+using Bit.Core.Services;
+using Stripe;
+
+namespace Bit.Core.Billing.Services.Implementations.AutomaticTax;
+
+public class BusinessUseAutomaticTaxStrategy(IFeatureService featureService) : IAutomaticTaxStrategy
+{
+    public SubscriptionUpdateOptions? GetUpdateOptions(Subscription subscription)
+    {
+        if (!featureService.IsEnabled(FeatureFlagKeys.PM19422_AllowAutomaticTaxUpdates))
+        {
+            return null;
+        }
+
+        var shouldBeEnabled = ShouldBeEnabled(subscription.Customer);
+        if (subscription.AutomaticTax.Enabled == shouldBeEnabled)
+        {
+            return null;
+        }
+
+        var options = new SubscriptionUpdateOptions
+        {
+            AutomaticTax = new SubscriptionAutomaticTaxOptions
+            {
+                Enabled = shouldBeEnabled
+            },
+            DefaultTaxRates = []
+        };
+
+        return options;
+    }
+
+    public void SetCreateOptions(SubscriptionCreateOptions options, Customer customer)
+    {
+        options.AutomaticTax = new SubscriptionAutomaticTaxOptions
+        {
+            Enabled = ShouldBeEnabled(customer)
+        };
+    }
+
+    public void SetUpdateOptions(SubscriptionUpdateOptions options, Subscription subscription)
+    {
+        if (!featureService.IsEnabled(FeatureFlagKeys.PM19422_AllowAutomaticTaxUpdates))
+        {
+            return;
+        }
+
+        var shouldBeEnabled = ShouldBeEnabled(subscription.Customer);
+
+        if (subscription.AutomaticTax.Enabled == shouldBeEnabled)
+        {
+            return;
+        }
+
+        options.AutomaticTax = new SubscriptionAutomaticTaxOptions
+        {
+            Enabled = shouldBeEnabled
+        };
+        options.DefaultTaxRates = [];
+    }
+
+    public void SetInvoiceCreatePreviewOptions(InvoiceCreatePreviewOptions options)
+    {
+        options.AutomaticTax ??= new InvoiceAutomaticTaxOptions();
+
+        if (options.CustomerDetails.Address.Country == "US")
+        {
+            options.AutomaticTax.Enabled = true;
+            return;
+        }
+
+        options.AutomaticTax.Enabled = options.CustomerDetails.TaxIds != null && options.CustomerDetails.TaxIds.Any();
+    }
+
+    private bool ShouldBeEnabled(Customer customer)
+    {
+        if (!customer.HasTaxLocationVerified())
+        {
+            return false;
+        }
+
+        if (customer.Address.Country == "US")
+        {
+            return true;
+        }
+
+        if (customer.TaxIds == null)
+        {
+            throw new ArgumentNullException(nameof(customer.TaxIds), "`customer.tax_ids` must be expanded.");
+        }
+
+        return customer.TaxIds.Any();
+    }
+}

src/Core/Billing/Services/Implementations/AutomaticTax/PersonalUseAutomaticTaxStrategy.cs

@@ -0,0 +1,64 @@
+#nullable enable
+using Bit.Core.Billing.Extensions;
+using Bit.Core.Services;
+using Stripe;
+
+namespace Bit.Core.Billing.Services.Implementations.AutomaticTax;
+
+public class PersonalUseAutomaticTaxStrategy(IFeatureService featureService) : IAutomaticTaxStrategy
+{
+    public void SetCreateOptions(SubscriptionCreateOptions options, Customer customer)
+    {
+        options.AutomaticTax = new SubscriptionAutomaticTaxOptions
+        {
+            Enabled = ShouldBeEnabled(customer)
+        };
+    }
+
+    public void SetUpdateOptions(SubscriptionUpdateOptions options, Subscription subscription)
+    {
+        if (!featureService.IsEnabled(FeatureFlagKeys.PM19422_AllowAutomaticTaxUpdates))
+        {
+            return;
+        }
+        options.AutomaticTax = new SubscriptionAutomaticTaxOptions
+        {
+            Enabled = ShouldBeEnabled(subscription.Customer)
+        };
+        options.DefaultTaxRates = [];
+    }
+
+    public SubscriptionUpdateOptions? GetUpdateOptions(Subscription subscription)
+    {
+        if (!featureService.IsEnabled(FeatureFlagKeys.PM19422_AllowAutomaticTaxUpdates))
+        {
+            return null;
+        }
+
+        if (subscription.AutomaticTax.Enabled == ShouldBeEnabled(subscription.Customer))
+        {
+            return null;
+        }
+
+        var options = new SubscriptionUpdateOptions
+        {
+            AutomaticTax = new SubscriptionAutomaticTaxOptions
+            {
+                Enabled = ShouldBeEnabled(subscription.Customer),
+            },
+            DefaultTaxRates = []
+        };
+
+        return options;
+    }
+
+    public void SetInvoiceCreatePreviewOptions(InvoiceCreatePreviewOptions options)
+    {
+        options.AutomaticTax = new InvoiceAutomaticTaxOptions { Enabled = true };
+    }
+
+    private static bool ShouldBeEnabled(Customer customer)
+    {
+        return customer.HasTaxLocationVerified();
+    }
+}

src/Core/Billing/Services/Implementations/OrganizationBillingService.cs

@@ -1,9 +1,11 @@
 using Bit.Core.AdminConsole.Entities;
 using Bit.Core.Billing.Caches;
 using Bit.Core.Billing.Constants;
+using Bit.Core.Billing.Extensions;
 using Bit.Core.Billing.Models;
 using Bit.Core.Billing.Models.Sales;
 using Bit.Core.Billing.Pricing;
+using Bit.Core.Billing.Services.Contracts;
 using Bit.Core.Enums;
 using Bit.Core.Exceptions;
 using Bit.Core.Repositories;
@@ -23,6 +25,7 @@ namespace Bit.Core.Billing.Services.Implementations;
 
 public class OrganizationBillingService(
     IBraintreeGateway braintreeGateway,
+    IFeatureService featureService,
     IGlobalSettings globalSettings,
     ILogger<OrganizationBillingService> logger,
     IOrganizationRepository organizationRepository,
@@ -30,7 +33,8 @@ public class OrganizationBillingService(
     ISetupIntentCache setupIntentCache,
     IStripeAdapter stripeAdapter,
     ISubscriberService subscriberService,
-    ITaxService taxService) : IOrganizationBillingService
+    ITaxService taxService,
+    IAutomaticTaxFactory automaticTaxFactory) : IOrganizationBillingService
 {
     public async Task Finalize(OrganizationSale sale)
     {
@@ -143,7 +147,7 @@ public class OrganizationBillingService(
             Coupon = customerSetup.Coupon,
             Description = organization.DisplayBusinessName(),
             Email = organization.BillingEmail,
-            Expand = ["tax"],
+            Expand = ["tax", "tax_ids"],
             InvoiceSettings = new CustomerInvoiceSettingsOptions
             {
                 CustomFields = [
@@ -369,21 +373,8 @@ public class OrganizationBillingService(
             }
         }
 
-        var customerHasTaxInfo = customer is
-        {
-            Address:
-            {
-                Country: not null and not "",
-                PostalCode: not null and not ""
-            }
-        };
-
         var subscriptionCreateOptions = new SubscriptionCreateOptions
         {
-            AutomaticTax = new SubscriptionAutomaticTaxOptions
-            {
-                Enabled = customerHasTaxInfo
-            },
             CollectionMethod = StripeConstants.CollectionMethod.ChargeAutomatically,
             Customer = customer.Id,
             Items = subscriptionItemOptionsList,
@@ -395,6 +386,18 @@ public class OrganizationBillingService(
             TrialPeriodDays = subscriptionSetup.SkipTrial ? 0 : plan.TrialPeriodDays
         };
 
+        if (featureService.IsEnabled(FeatureFlagKeys.PM19147_AutomaticTaxImprovements))
+        {
+            var automaticTaxParameters = new AutomaticTaxFactoryParameters(subscriptionSetup.PlanType);
+            var automaticTaxStrategy = await automaticTaxFactory.CreateAsync(automaticTaxParameters);
+            automaticTaxStrategy.SetCreateOptions(subscriptionCreateOptions, customer);
+        }
+        else
+        {
+            subscriptionCreateOptions.AutomaticTax ??= new SubscriptionAutomaticTaxOptions();
+            subscriptionCreateOptions.AutomaticTax.Enabled = customer.HasBillingLocation();
+        }
+
         return await stripeAdapter.SubscriptionCreateAsync(subscriptionCreateOptions);
     }
 

src/Core/Billing/Services/Implementations/PremiumUserBillingService.cs

@@ -2,6 +2,7 @@
 using Bit.Core.Billing.Constants;
 using Bit.Core.Billing.Models;
 using Bit.Core.Billing.Models.Sales;
+using Bit.Core.Billing.Services.Implementations.AutomaticTax;
 using Bit.Core.Entities;
 using Bit.Core.Enums;
 using Bit.Core.Exceptions;
@@ -9,6 +10,7 @@ using Bit.Core.Repositories;
 using Bit.Core.Services;
 using Bit.Core.Settings;
 using Braintree;
+using Microsoft.Extensions.DependencyInjection;
 using Microsoft.Extensions.Logging;
 using Stripe;
 using Customer = Stripe.Customer;
@@ -20,12 +22,14 @@ using static Utilities;
 
 public class PremiumUserBillingService(
     IBraintreeGateway braintreeGateway,
+    IFeatureService featureService,
     IGlobalSettings globalSettings,
     ILogger<PremiumUserBillingService> logger,
     ISetupIntentCache setupIntentCache,
     IStripeAdapter stripeAdapter,
     ISubscriberService subscriberService,
-    IUserRepository userRepository) : IPremiumUserBillingService
+    IUserRepository userRepository,
+    [FromKeyedServices(AutomaticTaxFactory.PersonalUse)] IAutomaticTaxStrategy automaticTaxStrategy) : IPremiumUserBillingService
 {
     public async Task Credit(User user, decimal amount)
     {
@@ -318,10 +322,6 @@ public class PremiumUserBillingService(
 
         var subscriptionCreateOptions = new SubscriptionCreateOptions
         {
-            AutomaticTax = new SubscriptionAutomaticTaxOptions
-            {
-                Enabled = customer.Tax?.AutomaticTax == StripeConstants.AutomaticTaxStatus.Supported,
-            },
             CollectionMethod = StripeConstants.CollectionMethod.ChargeAutomatically,
             Customer = customer.Id,
             Items = subscriptionItemOptionsList,
@@ -335,6 +335,18 @@ public class PremiumUserBillingService(
             OffSession = true
         };
 
+        if (featureService.IsEnabled(FeatureFlagKeys.PM19147_AutomaticTaxImprovements))
+        {
+            automaticTaxStrategy.SetCreateOptions(subscriptionCreateOptions, customer);
+        }
+        else
+        {
+            subscriptionCreateOptions.AutomaticTax = new SubscriptionAutomaticTaxOptions
+            {
+                Enabled = customer.Tax?.AutomaticTax == StripeConstants.AutomaticTaxStatus.Supported,
+            };
+        }
+
         var subscription = await stripeAdapter.SubscriptionCreateAsync(subscriptionCreateOptions);
 
         if (usingPayPal)

src/Core/Billing/Services/Implementations/SubscriberService.cs

@@ -1,6 +1,7 @@
 using Bit.Core.Billing.Caches;
 using Bit.Core.Billing.Constants;
 using Bit.Core.Billing.Models;
+using Bit.Core.Billing.Services.Contracts;
 using Bit.Core.Entities;
 using Bit.Core.Enums;
 using Bit.Core.Exceptions;
@@ -20,11 +21,13 @@ namespace Bit.Core.Billing.Services.Implementations;
 
 public class SubscriberService(
     IBraintreeGateway braintreeGateway,
+    IFeatureService featureService,
     IGlobalSettings globalSettings,
     ILogger<SubscriberService> logger,
     ISetupIntentCache setupIntentCache,
     IStripeAdapter stripeAdapter,
-    ITaxService taxService) : ISubscriberService
+    ITaxService taxService,
+    IAutomaticTaxFactory automaticTaxFactory) : ISubscriberService
 {
     public async Task CancelSubscription(
         ISubscriber subscriber,
@@ -438,7 +441,8 @@ public class SubscriberService(
         ArgumentNullException.ThrowIfNull(subscriber);
         ArgumentNullException.ThrowIfNull(tokenizedPaymentSource);
 
-        var customer = await GetCustomerOrThrow(subscriber);
+        var customerGetOptions = new CustomerGetOptions { Expand = ["tax", "tax_ids"] };
+        var customer = await GetCustomerOrThrow(subscriber, customerGetOptions);
 
         var (type, token) = tokenizedPaymentSource;
 
@@ -597,7 +601,7 @@ public class SubscriberService(
             Expand = ["subscriptions", "tax", "tax_ids"]
         });
 
-        await stripeAdapter.CustomerUpdateAsync(customer.Id, new CustomerUpdateOptions
+        customer = await stripeAdapter.CustomerUpdateAsync(customer.Id, new CustomerUpdateOptions
         {
             Address = new AddressOptions
             {
@@ -607,7 +611,8 @@ public class SubscriberService(
                 Line2 = taxInformation.Line2,
                 City = taxInformation.City,
                 State = taxInformation.State
-            }
+            },
+            Expand = ["subscriptions", "tax", "tax_ids"]
         });
 
         var taxId = customer.TaxIds?.FirstOrDefault();
@@ -661,21 +666,42 @@ public class SubscriberService(
             }
         }
 
-        if (SubscriberIsEligibleForAutomaticTax(subscriber, customer))
+        if (featureService.IsEnabled(FeatureFlagKeys.PM19147_AutomaticTaxImprovements))
         {
-            await stripeAdapter.SubscriptionUpdateAsync(subscriber.GatewaySubscriptionId,
-                new SubscriptionUpdateOptions
+            if (!string.IsNullOrEmpty(subscriber.GatewaySubscriptionId))
+            {
+                var subscriptionGetOptions = new SubscriptionGetOptions
                 {
-                    AutomaticTax = new SubscriptionAutomaticTaxOptions { Enabled = true }
-                });
+                    Expand = ["customer.tax", "customer.tax_ids"]
+                };
+                var subscription = await stripeAdapter.SubscriptionGetAsync(subscriber.GatewaySubscriptionId, subscriptionGetOptions);
+                var automaticTaxParameters = new AutomaticTaxFactoryParameters(subscriber, subscription.Items.Select(x => x.Price.Id));
+                var automaticTaxStrategy = await automaticTaxFactory.CreateAsync(automaticTaxParameters);
+                var automaticTaxOptions = automaticTaxStrategy.GetUpdateOptions(subscription);
+                if (automaticTaxOptions?.AutomaticTax?.Enabled != null)
+                {
+                    await stripeAdapter.SubscriptionUpdateAsync(subscriber.GatewaySubscriptionId, automaticTaxOptions);
+                }
+            }
         }
+        else
+        {
+            if (SubscriberIsEligibleForAutomaticTax(subscriber, customer))
+            {
+                await stripeAdapter.SubscriptionUpdateAsync(subscriber.GatewaySubscriptionId,
+                    new SubscriptionUpdateOptions
+                    {
+                        AutomaticTax = new SubscriptionAutomaticTaxOptions { Enabled = true }
+                    });
+            }
 
-        return;
+            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;
+            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(

src/Core/Constants.cs

@@ -148,6 +148,8 @@ public static class FeatureFlagKeys
     public const string P15179_AddExistingOrgsFromProviderPortal = "pm-15179-add-existing-orgs-from-provider-portal";
     public const string PM12276Breadcrumbing = "pm-12276-breadcrumbing-for-business-features";
     public const string PM18794_ProviderPaymentMethod = "pm-18794-provider-payment-method";
+    public const string PM19147_AutomaticTaxImprovements = "pm-19147-automatic-tax-improvements";
+    public const string PM19422_AllowAutomaticTaxUpdates = "pm-19422-allow-automatic-tax-updates";
 
     /* Key Management Team */
     public const string ReturnErrorOnExistingKeypair = "return-error-on-existing-keypair";
@@ -169,6 +171,7 @@ public static class FeatureFlagKeys
     public const string SingleTapPasskeyAuthentication = "single-tap-passkey-authentication";
     public const string EnablePMAuthenticatorSync = "enable-pm-bwa-sync";
     public const string PM3503_MobileAnonAddySelfHostAlias = "anon-addy-self-host-alias";
+
     public const string PM3553_MobileSimpleLoginSelfHostAlias = "simple-login-self-host-alias";
 
     /* Platform Team */

src/Core/Services/Implementations/StripePaymentService.cs

@@ -9,6 +9,8 @@ using Bit.Core.Billing.Models.Api.Responses;
 using Bit.Core.Billing.Models.Business;
 using Bit.Core.Billing.Pricing;
 using Bit.Core.Billing.Services;
+using Bit.Core.Billing.Services.Contracts;
+using Bit.Core.Billing.Services.Implementations.AutomaticTax;
 using Bit.Core.Entities;
 using Bit.Core.Enums;
 using Bit.Core.Exceptions;
@@ -16,6 +18,7 @@ using Bit.Core.Models.BitStripe;
 using Bit.Core.Models.Business;
 using Bit.Core.Repositories;
 using Bit.Core.Settings;
+using Microsoft.Extensions.DependencyInjection;
 using Microsoft.Extensions.Logging;
 using Stripe;
 using PaymentMethod = Stripe.PaymentMethod;
@@ -36,6 +39,8 @@ public class StripePaymentService : IPaymentService
     private readonly ITaxService _taxService;
     private readonly ISubscriberService _subscriberService;
     private readonly IPricingClient _pricingClient;
+    private readonly IAutomaticTaxFactory _automaticTaxFactory;
+    private readonly IAutomaticTaxStrategy _personalUseTaxStrategy;
 
     public StripePaymentService(
         ITransactionRepository transactionRepository,
@@ -46,7 +51,9 @@ public class StripePaymentService : IPaymentService
         IFeatureService featureService,
         ITaxService taxService,
         ISubscriberService subscriberService,
-        IPricingClient pricingClient)
+        IPricingClient pricingClient,
+        IAutomaticTaxFactory automaticTaxFactory,
+        [FromKeyedServices(AutomaticTaxFactory.PersonalUse)] IAutomaticTaxStrategy personalUseTaxStrategy)
     {
         _transactionRepository = transactionRepository;
         _logger = logger;
@@ -57,6 +64,8 @@ public class StripePaymentService : IPaymentService
         _taxService = taxService;
         _subscriberService = subscriberService;
         _pricingClient = pricingClient;
+        _automaticTaxFactory = automaticTaxFactory;
+        _personalUseTaxStrategy = personalUseTaxStrategy;
     }
 
     private async Task ChangeOrganizationSponsorship(
@@ -91,9 +100,7 @@ public class StripePaymentService : IPaymentService
         SubscriptionUpdate subscriptionUpdate, bool invoiceNow = false)
     {
         // remember, when in doubt, throw
-        var subGetOptions = new SubscriptionGetOptions();
-        // subGetOptions.AddExpand("customer");
-        subGetOptions.AddExpand("customer.tax");
+        var subGetOptions = new SubscriptionGetOptions { Expand = ["customer.tax", "customer.tax_ids"] };
         var sub = await _stripeAdapter.SubscriptionGetAsync(subscriber.GatewaySubscriptionId, subGetOptions);
         if (sub == null)
         {
@@ -124,7 +131,19 @@ public class StripePaymentService : IPaymentService
                 new SubscriptionPendingInvoiceItemIntervalOptions { Interval = "month" };
         }
 
-        subUpdateOptions.EnableAutomaticTax(sub.Customer, sub);
+        if (subscriptionUpdate is CompleteSubscriptionUpdate)
+        {
+            if (_featureService.IsEnabled(FeatureFlagKeys.PM19147_AutomaticTaxImprovements))
+            {
+                var automaticTaxParameters = new AutomaticTaxFactoryParameters(subscriber, updatedItemOptions.Select(x => x.Plan ?? x.Price));
+                var automaticTaxStrategy = await _automaticTaxFactory.CreateAsync(automaticTaxParameters);
+                automaticTaxStrategy.SetUpdateOptions(subUpdateOptions, sub);
+            }
+            else
+            {
+                subUpdateOptions.EnableAutomaticTax(sub.Customer, sub);
+            }
+        }
 
         if (!subscriptionUpdate.UpdateNeeded(sub))
         {
@@ -811,21 +830,46 @@ public class StripePaymentService : IPaymentService
                 });
             }
 
-            if (!string.IsNullOrEmpty(subscriber.GatewaySubscriptionId) &&
-                customer.Subscriptions.Any(sub =>
-                    sub.Id == subscriber.GatewaySubscriptionId &&
-                    !sub.AutomaticTax.Enabled) &&
-                customer.HasTaxLocationVerified())
+            if (_featureService.IsEnabled(FeatureFlagKeys.PM19147_AutomaticTaxImprovements))
             {
-                var subscriptionUpdateOptions = new SubscriptionUpdateOptions
+                if (!string.IsNullOrEmpty(subscriber.GatewaySubscriptionId))
                 {
-                    AutomaticTax = new SubscriptionAutomaticTaxOptions { Enabled = true },
-                    DefaultTaxRates = []
-                };
+                    var subscriptionGetOptions = new SubscriptionGetOptions
+                    {
+                        Expand = ["customer.tax", "customer.tax_ids"]
+                    };
+                    var subscription = await _stripeAdapter.SubscriptionGetAsync(subscriber.GatewaySubscriptionId, subscriptionGetOptions);
 
-                _ = await _stripeAdapter.SubscriptionUpdateAsync(
-                    subscriber.GatewaySubscriptionId,
-                    subscriptionUpdateOptions);
+                    var automaticTaxParameters = new AutomaticTaxFactoryParameters(subscriber, subscription.Items.Select(x => x.Price.Id));
+                    var automaticTaxStrategy = await _automaticTaxFactory.CreateAsync(automaticTaxParameters);
+                    var subscriptionUpdateOptions = automaticTaxStrategy.GetUpdateOptions(subscription);
+
+                    if (subscriptionUpdateOptions != null)
+                    {
+                        _ = await _stripeAdapter.SubscriptionUpdateAsync(
+                            subscriber.GatewaySubscriptionId,
+                            subscriptionUpdateOptions);
+                    }
+                }
+            }
+            else
+            {
+                if (!string.IsNullOrEmpty(subscriber.GatewaySubscriptionId) &&
+                    customer.Subscriptions.Any(sub =>
+                        sub.Id == subscriber.GatewaySubscriptionId &&
+                        !sub.AutomaticTax.Enabled) &&
+                    customer.HasTaxLocationVerified())
+                {
+                    var subscriptionUpdateOptions = new SubscriptionUpdateOptions
+                    {
+                        AutomaticTax = new SubscriptionAutomaticTaxOptions { Enabled = true },
+                        DefaultTaxRates = []
+                    };
+
+                    _ = await _stripeAdapter.SubscriptionUpdateAsync(
+                        subscriber.GatewaySubscriptionId,
+                        subscriptionUpdateOptions);
+                }
             }
         }
         catch
@@ -1214,6 +1258,8 @@ public class StripePaymentService : IPaymentService
             }
         }
 
+        _personalUseTaxStrategy.SetInvoiceCreatePreviewOptions(options);
+
         try
         {
             var invoice = await _stripeAdapter.InvoiceCreatePreviewAsync(options);
@@ -1256,10 +1302,6 @@ public class StripePaymentService : IPaymentService
 
         var options = new InvoiceCreatePreviewOptions
         {
-            AutomaticTax = new InvoiceAutomaticTaxOptions
-            {
-                Enabled = true,
-            },
             Currency = "usd",
             SubscriptionDetails = new InvoiceSubscriptionDetailsOptions
             {
@@ -1347,9 +1389,11 @@ public class StripePaymentService : IPaymentService
             ];
         }
 
+        Customer gatewayCustomer = null;
+
         if (!string.IsNullOrWhiteSpace(gatewayCustomerId))
         {
-            var gatewayCustomer = await _stripeAdapter.CustomerGetAsync(gatewayCustomerId);
+            gatewayCustomer = await _stripeAdapter.CustomerGetAsync(gatewayCustomerId);
 
             if (gatewayCustomer.Discount != null)
             {
@@ -1367,6 +1411,10 @@ public class StripePaymentService : IPaymentService
             }
         }
 
+        var automaticTaxFactoryParameters = new AutomaticTaxFactoryParameters(parameters.PasswordManager.Plan);
+        var automaticTaxStrategy = await _automaticTaxFactory.CreateAsync(automaticTaxFactoryParameters);
+        automaticTaxStrategy.SetInvoiceCreatePreviewOptions(options);
+
         try
         {
             var invoice = await _stripeAdapter.InvoiceCreatePreviewAsync(options);