Pm 19147 2 (#5544)

bitwarden_license/src/Commercial.Core/AdminConsole/Providers/RemoveOrganizationFromProviderCommand.cs

@@ -1,4 +1,5 @@
-using Bit.Core.AdminConsole.Entities;
+using Bit.Core;
+using Bit.Core.AdminConsole.Entities;
 using Bit.Core.AdminConsole.Entities.Provider;
 using Bit.Core.AdminConsole.OrganizationFeatures.OrganizationUsers.Interfaces;
 using Bit.Core.AdminConsole.Providers.Interfaces;
@@ -7,10 +8,12 @@ using Bit.Core.Billing.Constants;
 using Bit.Core.Billing.Extensions;
 using Bit.Core.Billing.Pricing;
 using Bit.Core.Billing.Services;
+using Bit.Core.Billing.Services.Implementations.AutomaticTax;
 using Bit.Core.Enums;
 using Bit.Core.Exceptions;
 using Bit.Core.Repositories;
 using Bit.Core.Services;
+using Microsoft.Extensions.DependencyInjection;
 using Stripe;
 
 namespace Bit.Commercial.Core.AdminConsole.Providers;
@@ -28,6 +31,7 @@ public class RemoveOrganizationFromProviderCommand : IRemoveOrganizationFromProv
     private readonly ISubscriberService _subscriberService;
     private readonly IHasConfirmedOwnersExceptQuery _hasConfirmedOwnersExceptQuery;
     private readonly IPricingClient _pricingClient;
+    private readonly IAutomaticTaxStrategy _automaticTaxStrategy;
 
     public RemoveOrganizationFromProviderCommand(
         IEventService eventService,
@@ -40,7 +44,8 @@ public class RemoveOrganizationFromProviderCommand : IRemoveOrganizationFromProv
         IProviderBillingService providerBillingService,
         ISubscriberService subscriberService,
         IHasConfirmedOwnersExceptQuery hasConfirmedOwnersExceptQuery,
-        IPricingClient pricingClient)
+        IPricingClient pricingClient,
+        [FromKeyedServices(AutomaticTaxFactory.BusinessUse)] IAutomaticTaxStrategy automaticTaxStrategy)
     {
         _eventService = eventService;
         _mailService = mailService;
@@ -53,6 +58,7 @@ public class RemoveOrganizationFromProviderCommand : IRemoveOrganizationFromProv
         _subscriberService = subscriberService;
         _hasConfirmedOwnersExceptQuery = hasConfirmedOwnersExceptQuery;
         _pricingClient = pricingClient;
+        _automaticTaxStrategy = automaticTaxStrategy;
     }
 
     public async Task RemoveOrganizationFromProvider(
@@ -107,7 +113,7 @@ public class RemoveOrganizationFromProviderCommand : IRemoveOrganizationFromProv
             organization.IsValidClient() &&
             !string.IsNullOrEmpty(organization.GatewayCustomerId))
         {
-            await _stripeAdapter.CustomerUpdateAsync(organization.GatewayCustomerId, new CustomerUpdateOptions
+            var customer = await _stripeAdapter.CustomerUpdateAsync(organization.GatewayCustomerId, new CustomerUpdateOptions
             {
                 Description = string.Empty,
                 Email = organization.BillingEmail
@@ -120,7 +126,6 @@ public class RemoveOrganizationFromProviderCommand : IRemoveOrganizationFromProv
                 Customer = organization.GatewayCustomerId,
                 CollectionMethod = StripeConstants.CollectionMethod.SendInvoice,
                 DaysUntilDue = 30,
-                AutomaticTax = new SubscriptionAutomaticTaxOptions { Enabled = true },
                 Metadata = new Dictionary<string, string>
                 {
                     { "organizationId", organization.Id.ToString() }
@@ -130,6 +135,18 @@ public class RemoveOrganizationFromProviderCommand : IRemoveOrganizationFromProv
                 Items = [new SubscriptionItemOptions { Price = plan.PasswordManager.StripeSeatPlanId, Quantity = organization.Seats }]
             };
 
+            if (_featureService.IsEnabled(FeatureFlagKeys.PM19147_AutomaticTaxImprovements))
+            {
+                _automaticTaxStrategy.SetCreateOptions(subscriptionCreateOptions, customer);
+            }
+            else
+            {
+                subscriptionCreateOptions.AutomaticTax ??= new SubscriptionAutomaticTaxOptions
+                {
+                    Enabled = true
+                };
+            }
+
             var subscription = await _stripeAdapter.SubscriptionCreateAsync(subscriptionCreateOptions);
 
             organization.GatewaySubscriptionId = subscription.Id;

bitwarden_license/src/Commercial.Core/Billing/ProviderBillingService.cs

@@ -14,6 +14,7 @@ using Bit.Core.Billing.Pricing;
 using Bit.Core.Billing.Repositories;
 using Bit.Core.Billing.Services;
 using Bit.Core.Billing.Services.Contracts;
+using Bit.Core.Billing.Services.Implementations.AutomaticTax;
 using Bit.Core.Enums;
 using Bit.Core.Exceptions;
 using Bit.Core.Models.Business;
@@ -22,6 +23,7 @@ using Bit.Core.Services;
 using Bit.Core.Settings;
 using Bit.Core.Utilities;
 using CsvHelper;
+using Microsoft.Extensions.DependencyInjection;
 using Microsoft.Extensions.Logging;
 using Stripe;
 
@@ -29,6 +31,7 @@ namespace Bit.Commercial.Core.Billing;
 
 public class ProviderBillingService(
     IEventService eventService,
+    IFeatureService featureService,
     IGlobalSettings globalSettings,
     ILogger<ProviderBillingService> logger,
     IOrganizationRepository organizationRepository,
@@ -40,7 +43,9 @@ public class ProviderBillingService(
     IProviderUserRepository providerUserRepository,
     IStripeAdapter stripeAdapter,
     ISubscriberService subscriberService,
-    ITaxService taxService) : IProviderBillingService
+    ITaxService taxService,
+    [FromKeyedServices(AutomaticTaxFactory.BusinessUse)] IAutomaticTaxStrategy automaticTaxStrategy)
+    : IProviderBillingService
 {
     [RequireFeature(FeatureFlagKeys.P15179_AddExistingOrgsFromProviderPortal)]
     public async Task AddExistingOrganization(
@@ -589,10 +594,6 @@ public class ProviderBillingService(
 
         var subscriptionCreateOptions = new SubscriptionCreateOptions
         {
-            AutomaticTax = new SubscriptionAutomaticTaxOptions
-            {
-                Enabled = true
-            },
             CollectionMethod = StripeConstants.CollectionMethod.SendInvoice,
             Customer = customer.Id,
             DaysUntilDue = 30,
@@ -605,6 +606,15 @@ public class ProviderBillingService(
             ProrationBehavior = StripeConstants.ProrationBehavior.CreateProrations
         };
 
+        if (featureService.IsEnabled(FeatureFlagKeys.PM19147_AutomaticTaxImprovements))
+        {
+            automaticTaxStrategy.SetCreateOptions(subscriptionCreateOptions, customer);
+        }
+        else
+        {
+            subscriptionCreateOptions.AutomaticTax = new SubscriptionAutomaticTaxOptions { Enabled = true };
+        }
+
         try
         {
             var subscription = await stripeAdapter.SubscriptionCreateAsync(subscriptionCreateOptions);

bitwarden_license/test/Commercial.Core.Test/AdminConsole/ProviderFeatures/RemoveOrganizationFromProviderCommandTests.cs

@@ -228,6 +228,26 @@ public class RemoveOrganizationFromProviderCommandTests
             Id = "subscription_id"
         });
 
+        sutProvider.GetDependency<IAutomaticTaxStrategy>()
+            .When(x => x.SetCreateOptions(
+                Arg.Is<SubscriptionCreateOptions>(options =>
+                    options.Customer == organization.GatewayCustomerId &&
+                    options.CollectionMethod == StripeConstants.CollectionMethod.SendInvoice &&
+                    options.DaysUntilDue == 30 &&
+                    options.Metadata["organizationId"] == organization.Id.ToString() &&
+                    options.OffSession == true &&
+                    options.ProrationBehavior == StripeConstants.ProrationBehavior.CreateProrations &&
+                    options.Items.First().Price == teamsMonthlyPlan.PasswordManager.StripeSeatPlanId &&
+                    options.Items.First().Quantity == organization.Seats)
+                , Arg.Any<Customer>()))
+            .Do(x =>
+            {
+                x.Arg<SubscriptionCreateOptions>().AutomaticTax = new SubscriptionAutomaticTaxOptions
+                {
+                    Enabled = true
+                };
+            });
+
         await sutProvider.Sut.RemoveOrganizationFromProvider(provider, providerOrganization, organization);
 
         await stripeAdapter.Received(1).SubscriptionCreateAsync(Arg.Is<SubscriptionCreateOptions>(options =>

bitwarden_license/test/Commercial.Core.Test/Billing/ProviderBillingServiceTests.cs

@@ -975,11 +975,12 @@ public class ProviderBillingServiceTests
     {
         provider.GatewaySubscriptionId = null;
 
-        sutProvider.GetDependency<ISubscriberService>().GetCustomerOrThrow(provider).Returns(new Customer
+        var customer = new Customer
         {
             Id = "customer_id",
             Tax = new CustomerTax { AutomaticTax = StripeConstants.AutomaticTaxStatus.Supported }
-        });
+        };
+        sutProvider.GetDependency<ISubscriberService>().GetCustomerOrThrow(provider).Returns(customer);
 
         var providerPlans = new List<ProviderPlan>
         {
@@ -1017,6 +1018,19 @@ public class ProviderBillingServiceTests
 
         var expected = new Subscription { Id = "subscription_id", Status = StripeConstants.SubscriptionStatus.Active };
 
+        sutProvider.GetDependency<IAutomaticTaxStrategy>()
+            .When(x => x.SetCreateOptions(
+                Arg.Is<SubscriptionCreateOptions>(options =>
+                    options.Customer == "customer_id")
+                , Arg.Is<Customer>(p => p == customer)))
+            .Do(x =>
+            {
+                x.Arg<SubscriptionCreateOptions>().AutomaticTax = new SubscriptionAutomaticTaxOptions
+                {
+                    Enabled = true
+                };
+            });
+
         sutProvider.GetDependency<IStripeAdapter>().SubscriptionCreateAsync(Arg.Is<SubscriptionCreateOptions>(
             sub =>
                 sub.AutomaticTax.Enabled == true &&

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 +1,19 @@
+#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);
+    void SetCreateOptions(SubscriptionCreateOptions options, Customer customer);
+    void SetUpdateOptions(SubscriptionUpdateOptions options, Subscription subscription);
+}

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

@@ -0,0 +1,51 @@
+#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;
+        var plans = await pricingClient.ListPlans();
+
+        if (personalUsePlans.Any(x => plans.Any(y => y.PasswordManager.StripePlanId == x)))
+        {
+            return new PersonalUseAutomaticTaxStrategy(featureService);
+        }
+
+        return new BusinessUseAutomaticTaxStrategy(featureService);
+    }
+}

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

@@ -0,0 +1,78 @@
+#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 = [];
+    }
+
+    private bool ShouldBeEnabled(Customer customer)
+    {
+        if (!customer.HasTaxLocationVerified())
+        {
+            return false;
+        }
+
+        if (customer.Address.Country == "US")
+        {
+            return true;
+        }
+
+        return customer.TaxIds != null && customer.TaxIds.Any();
+    }
+}

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

@@ -0,0 +1,59 @@
+#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;
+    }
+
+    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)
     {
@@ -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,
@@ -597,7 +600,7 @@ 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
             {
@@ -661,6 +664,22 @@ public class SubscriberService(
             }
         }
 
+        if (featureService.IsEnabled(FeatureFlagKeys.PM19147_AutomaticTaxImprovements))
+        {
+            if (!string.IsNullOrEmpty(subscriber.GatewaySubscriptionId))
+            {
+                var subscription = await stripeAdapter.SubscriptionGetAsync(subscriber.GatewaySubscriptionId);
+                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,
@@ -677,6 +696,7 @@ public class SubscriberService(
                    (localCustomer.Subscriptions?.Any(sub => sub.Id == localSubscriber.GatewaySubscriptionId && !sub.AutomaticTax.Enabled) ?? false) &&
                    localCustomer.Tax?.AutomaticTax == StripeConstants.AutomaticTaxStatus.Supported;
         }
+    }
 
     public async Task VerifyBankAccount(
         ISubscriber subscriber,

src/Core/Constants.cs

@@ -178,6 +178,8 @@ public static class FeatureFlagKeys
     public const string PM3503_MobileAnonAddySelfHostAlias = "anon-addy-self-host-alias";
     public const string WebPush = "web-push";
     public const string AndroidImportLoginsFlow = "import-logins-flow";
+    public const string PM19147_AutomaticTaxImprovements = "pm-19147-automatic-tax-improvements";
+    public const string PM19422_AllowAutomaticTaxUpdates = "pm-19422-allow-automatic-tax-updates";
     public const string PM12276Breadcrumbing = "pm-12276-breadcrumbing-for-business-features";
     public const string PM18794_ProviderPaymentMethod = "pm-18794-provider-payment-method";
     public const string PM3553_MobileSimpleLoginSelfHostAlias = "simple-login-self-host-alias";

src/Core/Services/Implementations/StripePaymentService.cs

@@ -9,6 +9,7 @@ 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.Entities;
 using Bit.Core.Enums;
 using Bit.Core.Exceptions;
@@ -36,6 +37,7 @@ public class StripePaymentService : IPaymentService
     private readonly ITaxService _taxService;
     private readonly ISubscriberService _subscriberService;
     private readonly IPricingClient _pricingClient;
+    private readonly IAutomaticTaxFactory _automaticTaxFactory;
 
     public StripePaymentService(
         ITransactionRepository transactionRepository,
@@ -46,7 +48,8 @@ public class StripePaymentService : IPaymentService
         IFeatureService featureService,
         ITaxService taxService,
         ISubscriberService subscriberService,
-        IPricingClient pricingClient)
+        IPricingClient pricingClient,
+        IAutomaticTaxFactory automaticTaxFactory)
     {
         _transactionRepository = transactionRepository;
         _logger = logger;
@@ -57,6 +60,7 @@ public class StripePaymentService : IPaymentService
         _taxService = taxService;
         _subscriberService = subscriberService;
         _pricingClient = pricingClient;
+        _automaticTaxFactory = automaticTaxFactory;
     }
 
     private async Task ChangeOrganizationSponsorship(
@@ -124,7 +128,16 @@ public class StripePaymentService : IPaymentService
                 new SubscriptionPendingInvoiceItemIntervalOptions { Interval = "month" };
         }
 
+        if (_featureService.IsEnabled(FeatureFlagKeys.PM19147_AutomaticTaxImprovements))
+        {
+            var automaticTaxParameters = new AutomaticTaxFactoryParameters(subscriber, updatedItemOptions.Select(x => x.Price));
+            var automaticTaxStrategy = await _automaticTaxFactory.CreateAsync(automaticTaxParameters);
+            automaticTaxStrategy.SetUpdateOptions(subUpdateOptions, sub);
+        }
+        else
+        {
             subUpdateOptions.EnableAutomaticTax(sub.Customer, sub);
+        }
 
         if (!subscriptionUpdate.UpdateNeeded(sub))
         {
@@ -811,6 +824,26 @@ public class StripePaymentService : IPaymentService
                 });
             }
 
+            if (_featureService.IsEnabled(FeatureFlagKeys.PM19147_AutomaticTaxImprovements))
+            {
+                if (!string.IsNullOrEmpty(subscriber.GatewaySubscriptionId))
+                {
+                    var subscription = await _stripeAdapter.SubscriptionGetAsync(subscriber.GatewaySubscriptionId);
+
+                    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 &&
@@ -828,6 +861,7 @@ public class StripePaymentService : IPaymentService
                         subscriptionUpdateOptions);
                 }
             }
+        }
         catch
         {
             if (braintreeCustomer != null && !hadBtCustomer)

test/Core.Test/Billing/Services/SubscriberServiceTests.cs

@@ -3,10 +3,13 @@ using Bit.Core.AdminConsole.Entities.Provider;
 using Bit.Core.Billing.Caches;
 using Bit.Core.Billing.Constants;
 using Bit.Core.Billing.Models;
+using Bit.Core.Billing.Services;
+using Bit.Core.Billing.Services.Contracts;
 using Bit.Core.Billing.Services.Implementations;
 using Bit.Core.Enums;
 using Bit.Core.Services;
 using Bit.Core.Settings;
+using Bit.Core.Test.Billing.Stubs;
 using Bit.Test.Common.AutoFixture;
 using Bit.Test.Common.AutoFixture.Attributes;
 using Braintree;
@@ -1561,6 +1564,37 @@ public class SubscriberServiceTests
             "Example Town",
             "NY");
 
+        sutProvider.GetDependency<IStripeAdapter>()
+            .CustomerUpdateAsync(
+                Arg.Is<string>(p => p == provider.GatewayCustomerId),
+                Arg.Is<CustomerUpdateOptions>(options =>
+                    options.Address.Country == "US" &&
+                    options.Address.PostalCode == "12345" &&
+                    options.Address.Line1 == "123 Example St." &&
+                    options.Address.Line2 == null &&
+                    options.Address.City == "Example Town" &&
+                    options.Address.State == "NY"))
+            .Returns(new Customer
+            {
+                Id = provider.GatewayCustomerId,
+                Address = new Address
+                {
+                    Country = "US",
+                    PostalCode = "12345",
+                    Line1 = "123 Example St.",
+                    Line2 = null,
+                    City = "Example Town",
+                    State = "NY"
+                },
+                TaxIds = new StripeList<TaxId> { Data = [new TaxId { Id = "tax_id_1", Type = "us_ein" }] }
+            });
+
+        var subscription = new Subscription { Items = new StripeList<SubscriptionItem>() };
+        sutProvider.GetDependency<IStripeAdapter>().SubscriptionGetAsync(Arg.Any<string>())
+            .Returns(subscription);
+        sutProvider.GetDependency<IAutomaticTaxFactory>().CreateAsync(Arg.Any<AutomaticTaxFactoryParameters>())
+            .Returns(new FakeAutomaticTaxStrategy(true));
+
         await sutProvider.Sut.UpdateTaxInformation(provider, taxInformation);
 
         await stripeAdapter.Received(1).CustomerUpdateAsync(provider.GatewayCustomerId, Arg.Is<CustomerUpdateOptions>(

test/Core.Test/Billing/Stubs/FakeAutomaticTaxStrategy.cs

@@ -0,0 +1,29 @@
+using Bit.Core.Billing.Services;
+using Stripe;
+
+namespace Bit.Core.Test.Billing.Stubs;
+
+/// <param name="IsAutomaticTaxEnabled">
+/// Whether the subscription options will have automatic tax enabled or not.
+/// </param>
+public class FakeAutomaticTaxStrategy(
+    bool IsAutomaticTaxEnabled) : IAutomaticTaxStrategy
+{
+    public SubscriptionUpdateOptions? GetUpdateOptions(Subscription subscription)
+    {
+        return new SubscriptionUpdateOptions
+        {
+            AutomaticTax = new SubscriptionAutomaticTaxOptions { Enabled = IsAutomaticTaxEnabled }
+        };
+    }
+
+    public void SetCreateOptions(SubscriptionCreateOptions options, Customer customer)
+    {
+        options.AutomaticTax = new SubscriptionAutomaticTaxOptions { Enabled = IsAutomaticTaxEnabled };
+    }
+
+    public void SetUpdateOptions(SubscriptionUpdateOptions options, Subscription subscription)
+    {
+        options.AutomaticTax = new SubscriptionAutomaticTaxOptions { Enabled = IsAutomaticTaxEnabled };
+    }
+}