[PM-5766] Automatic Tax Feature Flag (#3729)

* Added feature flag constant

* Wrapped Automatic Tax logic behind feature flag

* Only getting customer if feature is anabled.

* Enabled feature flag in unit tests

* Made IPaymentService scoped

* Added missing StripeFacade calls

src/Billing/Controllers/StripeController.cs

@@ -1,6 +1,7 @@
 using Bit.Billing.Constants;
 using Bit.Billing.Models;
 using Bit.Billing.Services;
+using Bit.Core;
 using Bit.Core.AdminConsole.Entities;
 using Bit.Core.Context;
 using Bit.Core.Enums;
@@ -23,6 +24,7 @@ using Event = Stripe.Event;
 using JsonSerializer = System.Text.Json.JsonSerializer;
 using PaymentMethod = Stripe.PaymentMethod;
 using Subscription = Stripe.Subscription;
+using TaxRate = Bit.Core.Entities.TaxRate;
 using Transaction = Bit.Core.Entities.Transaction;
 using TransactionType = Bit.Core.Enums.TransactionType;
 
@@ -52,6 +54,7 @@ public class StripeController : Controller
     private readonly GlobalSettings _globalSettings;
     private readonly IStripeEventService _stripeEventService;
     private readonly IStripeFacade _stripeFacade;
+    private readonly IFeatureService _featureService;
 
     public StripeController(
         GlobalSettings globalSettings,
@@ -70,7 +73,8 @@ public class StripeController : Controller
         IUserRepository userRepository,
         ICurrentContext currentContext,
         IStripeEventService stripeEventService,
-        IStripeFacade stripeFacade)
+        IStripeFacade stripeFacade,
+        IFeatureService featureService)
     {
         _billingSettings = billingSettings?.Value;
         _hostingEnvironment = hostingEnvironment;
@@ -97,6 +101,7 @@ public class StripeController : Controller
         _globalSettings = globalSettings;
         _stripeEventService = stripeEventService;
         _stripeFacade = stripeFacade;
+        _featureService = featureService;
     }
 
     [HttpPost("webhook")]
@@ -242,17 +247,29 @@ public class StripeController : Controller
                     $"Received null Subscription from Stripe for ID '{invoice.SubscriptionId}' while processing Event with ID '{parsedEvent.Id}'");
             }
 
-            if (!subscription.AutomaticTax.Enabled)
+            var pm5766AutomaticTaxIsEnabled = _featureService.IsEnabled(FeatureFlagKeys.PM5766AutomaticTax);
+            if (pm5766AutomaticTaxIsEnabled)
             {
-                subscription = await _stripeFacade.UpdateSubscription(subscription.Id,
-                    new SubscriptionUpdateOptions
-                    {
-                        DefaultTaxRates = new List<string>(),
-                        AutomaticTax = new SubscriptionAutomaticTaxOptions { Enabled = true }
-                    });
+                var customer = await _stripeFacade.GetCustomer(subscription.CustomerId);
+                if (!subscription.AutomaticTax.Enabled &&
+                    !string.IsNullOrEmpty(customer.Address?.PostalCode) &&
+                    !string.IsNullOrEmpty(customer.Address?.Country))
+                {
+                    subscription = await _stripeFacade.UpdateSubscription(subscription.Id,
+                        new SubscriptionUpdateOptions
+                        {
+                            DefaultTaxRates = new List<string>(),
+                            AutomaticTax = new SubscriptionAutomaticTaxOptions { Enabled = true }
+                        });
+                }
             }
 
-            var (organizationId, userId) = GetIdsFromMetaData(subscription.Metadata);
+
+            var updatedSubscription = pm5766AutomaticTaxIsEnabled
+                ? subscription
+                : await VerifyCorrectTaxRateForCharge(invoice, subscription);
+
+            var (organizationId, userId) = GetIdsFromMetaData(updatedSubscription.Metadata);
 
             var invoiceLineItemDescriptions = invoice.Lines.Select(i => i.Description).ToList();
 
@@ -273,7 +290,7 @@ public class StripeController : Controller
 
             if (organizationId.HasValue)
             {
-                if (IsSponsoredSubscription(subscription))
+                if (IsSponsoredSubscription(updatedSubscription))
                 {
                     await _validateSponsorshipCommand.ValidateSponsorshipAsync(organizationId.Value);
                 }
@@ -321,22 +338,20 @@ public class StripeController : Controller
 
             Tuple<Guid?, Guid?> ids = null;
             Subscription subscription = null;
-            var subscriptionService = new SubscriptionService();
 
             if (charge.InvoiceId != null)
             {
-                var invoiceService = new InvoiceService();
-                var invoice = await invoiceService.GetAsync(charge.InvoiceId);
+                var invoice = await _stripeFacade.GetInvoice(charge.InvoiceId);
                 if (invoice?.SubscriptionId != null)
                 {
-                    subscription = await subscriptionService.GetAsync(invoice.SubscriptionId);
+                    subscription = await _stripeFacade.GetSubscription(invoice.SubscriptionId);
                     ids = GetIdsFromMetaData(subscription?.Metadata);
                 }
             }
 
             if (subscription == null || ids == null || (ids.Item1.HasValue && ids.Item2.HasValue))
             {
-                var subscriptions = await subscriptionService.ListAsync(new SubscriptionListOptions
+                var subscriptions = await _stripeFacade.ListSubscriptions(new SubscriptionListOptions
                 {
                     Customer = charge.CustomerId
                 });
@@ -490,8 +505,7 @@ public class StripeController : Controller
             var invoice = await _stripeEventService.GetInvoice(parsedEvent, true);
             if (invoice.Paid && invoice.BillingReason == "subscription_create")
             {
-                var subscriptionService = new SubscriptionService();
-                var subscription = await subscriptionService.GetAsync(invoice.SubscriptionId);
+                var subscription = await _stripeFacade.GetSubscription(invoice.SubscriptionId);
                 if (subscription?.Status == StripeSubscriptionStatus.Active)
                 {
                     if (DateTime.UtcNow - invoice.Created < TimeSpan.FromMinutes(1))
@@ -596,7 +610,6 @@ public class StripeController : Controller
             return;
         }
 
-        var subscriptionService = new SubscriptionService();
         var subscriptionListOptions = new SubscriptionListOptions
         {
             Customer = paymentMethod.CustomerId,
@@ -607,7 +620,7 @@ public class StripeController : Controller
         StripeList<Subscription> unpaidSubscriptions;
         try
         {
-            unpaidSubscriptions = await subscriptionService.ListAsync(subscriptionListOptions);
+            unpaidSubscriptions = await _stripeFacade.ListSubscriptions(subscriptionListOptions);
         }
         catch (Exception e)
         {
@@ -702,8 +715,7 @@ public class StripeController : Controller
 
     private async Task<bool> AttemptToPayInvoiceAsync(Invoice invoice, bool attemptToPayWithStripe = false)
     {
-        var customerService = new CustomerService();
-        var customer = await customerService.GetAsync(invoice.CustomerId);
+        var customer = await _stripeFacade.GetCustomer(invoice.CustomerId);
 
         if (customer?.Metadata?.ContainsKey("btCustomerId") ?? false)
         {
@@ -728,8 +740,7 @@ public class StripeController : Controller
             return false;
         }
 
-        var subscriptionService = new SubscriptionService();
-        var subscription = await subscriptionService.GetAsync(invoice.SubscriptionId);
+        var subscription = await _stripeFacade.GetSubscription(invoice.SubscriptionId);
         var ids = GetIdsFromMetaData(subscription?.Metadata);
         if (!ids.Item1.HasValue && !ids.Item2.HasValue)
         {
@@ -797,10 +808,9 @@ public class StripeController : Controller
             return false;
         }
 
-        var invoiceService = new InvoiceService();
         try
         {
-            await invoiceService.UpdateAsync(invoice.Id, new InvoiceUpdateOptions
+            await _stripeFacade.UpdateInvoice(invoice.Id, new InvoiceUpdateOptions
             {
                 Metadata = new Dictionary<string, string>
                 {
@@ -809,14 +819,14 @@ public class StripeController : Controller
                         transactionResult.Target.PayPalDetails?.AuthorizationId
                 }
             });
-            await invoiceService.PayAsync(invoice.Id, new InvoicePayOptions { PaidOutOfBand = true });
+            await _stripeFacade.PayInvoice(invoice.Id, new InvoicePayOptions { PaidOutOfBand = true });
         }
         catch (Exception e)
         {
             await _btGateway.Transaction.RefundAsync(transactionResult.Target.Id);
             if (e.Message.Contains("Invoice is already paid"))
             {
-                await invoiceService.UpdateAsync(invoice.Id, new InvoiceUpdateOptions
+                await _stripeFacade.UpdateInvoice(invoice.Id, new InvoiceUpdateOptions
                 {
                     Metadata = invoice.Metadata
                 });
@@ -834,8 +844,7 @@ public class StripeController : Controller
     {
         try
         {
-            var invoiceService = new InvoiceService();
-            await invoiceService.PayAsync(invoice.Id);
+            await _stripeFacade.PayInvoice(invoice.Id);
             return true;
         }
         catch (Exception e)
@@ -855,6 +864,41 @@ public class StripeController : Controller
             invoice.BillingReason == "subscription_cycle" && invoice.SubscriptionId != null;
     }
 
+    private async Task<Subscription> VerifyCorrectTaxRateForCharge(Invoice invoice, Subscription subscription)
+    {
+        if (string.IsNullOrWhiteSpace(invoice?.CustomerAddress?.Country) ||
+            string.IsNullOrWhiteSpace(invoice?.CustomerAddress?.PostalCode))
+        {
+            return subscription;
+        }
+
+        var localBitwardenTaxRates = await _taxRateRepository.GetByLocationAsync(
+            new TaxRate()
+            {
+                Country = invoice.CustomerAddress.Country,
+                PostalCode = invoice.CustomerAddress.PostalCode
+            }
+        );
+
+        if (!localBitwardenTaxRates.Any())
+        {
+            return subscription;
+        }
+
+        var stripeTaxRate = await _stripeFacade.GetTaxRate(localBitwardenTaxRates.First().Id);
+        if (stripeTaxRate == null || subscription.DefaultTaxRates.Any(x => x == stripeTaxRate))
+        {
+            return subscription;
+        }
+
+        subscription.DefaultTaxRates = new List<Stripe.TaxRate> { stripeTaxRate };
+
+        var subscriptionOptions = new SubscriptionUpdateOptions { DefaultTaxRates = new List<string> { stripeTaxRate.Id } };
+        subscription = await _stripeFacade.UpdateSubscription(subscription.Id, subscriptionOptions);
+
+        return subscription;
+    }
+
     private static bool IsSponsoredSubscription(Subscription subscription) =>
         StaticStore.SponsoredPlans.Any(p => p.StripePlanId == subscription.Id);
 
@@ -862,8 +906,7 @@ public class StripeController : Controller
     {
         if (!invoice.Paid && invoice.AttemptCount > 1 && UnpaidAutoChargeInvoiceForSubscriptionCycle(invoice))
         {
-            var subscriptionService = new SubscriptionService();
-            var subscription = await subscriptionService.GetAsync(invoice.SubscriptionId);
+            var subscription = await _stripeFacade.GetSubscription(invoice.SubscriptionId);
             // attempt count 4 = 11 days after initial failure
             if (invoice.AttemptCount <= 3 ||
                 !subscription.Items.Any(i => i.Price.Id is PremiumPlanId or PremiumPlanIdAppStore))
@@ -873,23 +916,20 @@ public class StripeController : Controller
         }
     }
 
-    private async Task CancelSubscription(string subscriptionId)
-    {
-        await new SubscriptionService().CancelAsync(subscriptionId, new SubscriptionCancelOptions());
-    }
+    private async Task CancelSubscription(string subscriptionId) =>
+        await _stripeFacade.CancelSubscription(subscriptionId, new SubscriptionCancelOptions());
 
     private async Task VoidOpenInvoices(string subscriptionId)
     {
-        var invoiceService = new InvoiceService();
         var options = new InvoiceListOptions
         {
             Status = StripeInvoiceStatus.Open,
             Subscription = subscriptionId
         };
-        var invoices = invoiceService.List(options);
+        var invoices = await _stripeFacade.ListInvoices(options);
         foreach (var invoice in invoices)
         {
-            await invoiceService.VoidInvoiceAsync(invoice.Id);
+            await _stripeFacade.VoidInvoice(invoice.Id);
         }
     }
 

src/Billing/Services/IStripeFacade.cs

@@ -22,12 +22,40 @@ public interface IStripeFacade
         RequestOptions requestOptions = null,
         CancellationToken cancellationToken = default);
 
+    Task<StripeList<Invoice>> ListInvoices(
+        InvoiceListOptions options = null,
+        RequestOptions requestOptions = null,
+        CancellationToken cancellationToken = default);
+
+    Task<Invoice> UpdateInvoice(
+        string invoiceId,
+        InvoiceUpdateOptions invoiceGetOptions = null,
+        RequestOptions requestOptions = null,
+        CancellationToken cancellationToken = default);
+
+    Task<Invoice> PayInvoice(
+        string invoiceId,
+        InvoicePayOptions options = null,
+        RequestOptions requestOptions = null,
+        CancellationToken cancellationToken = default);
+
+    Task<Invoice> VoidInvoice(
+        string invoiceId,
+        InvoiceVoidOptions options = null,
+        RequestOptions requestOptions = null,
+        CancellationToken cancellationToken = default);
+
     Task<PaymentMethod> GetPaymentMethod(
         string paymentMethodId,
         PaymentMethodGetOptions paymentMethodGetOptions = null,
         RequestOptions requestOptions = null,
         CancellationToken cancellationToken = default);
 
+    Task<StripeList<Subscription>> ListSubscriptions(
+        SubscriptionListOptions options = null,
+        RequestOptions requestOptions = null,
+        CancellationToken cancellationToken = default);
+
     Task<Subscription> GetSubscription(
         string subscriptionId,
         SubscriptionGetOptions subscriptionGetOptions = null,
@@ -39,4 +67,16 @@ public interface IStripeFacade
         SubscriptionUpdateOptions subscriptionGetOptions = null,
         RequestOptions requestOptions = null,
         CancellationToken cancellationToken = default);
+
+    Task<Subscription> CancelSubscription(
+        string subscriptionId,
+        SubscriptionCancelOptions options = null,
+        RequestOptions requestOptions = null,
+        CancellationToken cancellationToken = default);
+
+    Task<TaxRate> GetTaxRate(
+        string taxRateId,
+        TaxRateGetOptions options = null,
+        RequestOptions requestOptions = null,
+        CancellationToken cancellationToken = default);
 }

src/Billing/Services/Implementations/StripeFacade.cs

@@ -9,6 +9,7 @@ public class StripeFacade : IStripeFacade
     private readonly InvoiceService _invoiceService = new();
     private readonly PaymentMethodService _paymentMethodService = new();
     private readonly SubscriptionService _subscriptionService = new();
+    private readonly TaxRateService _taxRateService = new();
 
     public async Task<Charge> GetCharge(
         string chargeId,
@@ -31,6 +32,31 @@ public class StripeFacade : IStripeFacade
         CancellationToken cancellationToken = default) =>
         await _invoiceService.GetAsync(invoiceId, invoiceGetOptions, requestOptions, cancellationToken);
 
+    public async Task<StripeList<Invoice>> ListInvoices(
+        InvoiceListOptions options = null,
+        RequestOptions requestOptions = null,
+        CancellationToken cancellationToken = default) =>
+        await _invoiceService.ListAsync(options, requestOptions, cancellationToken);
+
+    public async Task<Invoice> UpdateInvoice(
+        string invoiceId,
+        InvoiceUpdateOptions invoiceGetOptions = null,
+        RequestOptions requestOptions = null,
+        CancellationToken cancellationToken = default) =>
+        await _invoiceService.UpdateAsync(invoiceId, invoiceGetOptions, requestOptions, cancellationToken);
+
+    public async Task<Invoice> PayInvoice(string invoiceId, InvoicePayOptions options = null,
+        RequestOptions requestOptions = null,
+        CancellationToken cancellationToken = default) =>
+        await _invoiceService.PayAsync(invoiceId, options, requestOptions, cancellationToken);
+
+    public async Task<Invoice> VoidInvoice(
+        string invoiceId,
+        InvoiceVoidOptions options = null,
+        RequestOptions requestOptions = null,
+        CancellationToken cancellationToken = default) =>
+        await _invoiceService.VoidInvoiceAsync(invoiceId, options, requestOptions, cancellationToken);
+
     public async Task<PaymentMethod> GetPaymentMethod(
         string paymentMethodId,
         PaymentMethodGetOptions paymentMethodGetOptions = null,
@@ -38,6 +64,11 @@ public class StripeFacade : IStripeFacade
         CancellationToken cancellationToken = default) =>
         await _paymentMethodService.GetAsync(paymentMethodId, paymentMethodGetOptions, requestOptions, cancellationToken);
 
+    public async Task<StripeList<Subscription>> ListSubscriptions(SubscriptionListOptions options = null,
+        RequestOptions requestOptions = null,
+        CancellationToken cancellationToken = default) =>
+        await _subscriptionService.ListAsync(options, requestOptions, cancellationToken);
+
     public async Task<Subscription> GetSubscription(
         string subscriptionId,
         SubscriptionGetOptions subscriptionGetOptions = null,
@@ -51,4 +82,18 @@ public class StripeFacade : IStripeFacade
         RequestOptions requestOptions = null,
         CancellationToken cancellationToken = default) =>
         await _subscriptionService.UpdateAsync(subscriptionId, subscriptionUpdateOptions, requestOptions, cancellationToken);
+
+    public async Task<Subscription> CancelSubscription(
+        string subscriptionId,
+        SubscriptionCancelOptions options = null,
+        RequestOptions requestOptions = null,
+        CancellationToken cancellationToken = default) =>
+        await _subscriptionService.CancelAsync(subscriptionId, options, requestOptions, cancellationToken);
+
+    public async Task<TaxRate> GetTaxRate(
+        string taxRateId,
+        TaxRateGetOptions options = null,
+        RequestOptions requestOptions = null,
+        CancellationToken cancellationToken = default) =>
+        await _taxRateService.GetAsync(taxRateId, options, requestOptions, cancellationToken);
 }

src/Core/AdminConsole/Services/Implementations/OrganizationService.cs

@@ -139,8 +139,13 @@ public class OrganizationService : IOrganizationService
         }
 
         await _paymentService.SaveTaxInfoAsync(organization, taxInfo);
-        var updated = await _paymentService.UpdatePaymentMethodAsync(organization,
-            paymentMethodType, paymentToken, taxInfo);
+        var updated = await _paymentService.UpdatePaymentMethodAsync(
+            organization,
+            paymentMethodType,
+            paymentToken,
+            _featureService.IsEnabled(FeatureFlagKeys.PM5766AutomaticTax)
+                ? taxInfo
+                : null);
         if (updated)
         {
             await ReplaceAndUpdateCacheAsync(organization);

src/Core/Constants.cs

@@ -116,6 +116,8 @@ public static class FeatureFlagKeys
     /// </summary>
     public const string FlexibleCollectionsMigration = "flexible-collections-migration";
 
+    public const string PM5766AutomaticTax = "PM-5766-automatic-tax";
+
     public static List<string> GetAllKeys()
     {
         return typeof(FeatureFlagKeys).GetFields(BindingFlags.Public | BindingFlags.Static | BindingFlags.FlattenHierarchy)

src/Core/Services/Implementations/StripePaymentService.cs

@@ -21,29 +21,29 @@ public class StripePaymentService : IPaymentService
     private const string SecretsManagerStandaloneDiscountId = "sm-standalone";
 
     private readonly ITransactionRepository _transactionRepository;
-    private readonly IUserRepository _userRepository;
     private readonly ILogger<StripePaymentService> _logger;
     private readonly Braintree.IBraintreeGateway _btGateway;
     private readonly ITaxRateRepository _taxRateRepository;
     private readonly IStripeAdapter _stripeAdapter;
     private readonly IGlobalSettings _globalSettings;
+    private readonly IFeatureService _featureService;
 
     public StripePaymentService(
         ITransactionRepository transactionRepository,
-        IUserRepository userRepository,
         ILogger<StripePaymentService> logger,
         ITaxRateRepository taxRateRepository,
         IStripeAdapter stripeAdapter,
         Braintree.IBraintreeGateway braintreeGateway,
-        IGlobalSettings globalSettings)
+        IGlobalSettings globalSettings,
+        IFeatureService featureService)
     {
         _transactionRepository = transactionRepository;
-        _userRepository = userRepository;
         _logger = logger;
         _taxRateRepository = taxRateRepository;
         _stripeAdapter = stripeAdapter;
         _btGateway = braintreeGateway;
         _globalSettings = globalSettings;
+        _featureService = featureService;
     }
 
     public async Task<string> PurchaseOrganizationAsync(Organization org, PaymentMethodType paymentMethodType,
@@ -100,6 +100,28 @@ public class StripePaymentService : IPaymentService
             throw new GatewayException("Payment method is not supported at this time.");
         }
 
+        var pm5766AutomaticTaxIsEnabled = _featureService.IsEnabled(FeatureFlagKeys.PM5766AutomaticTax);
+
+        if (!pm5766AutomaticTaxIsEnabled &&
+            taxInfo != null &&
+            !string.IsNullOrWhiteSpace(taxInfo.BillingAddressCountry) &&
+            !string.IsNullOrWhiteSpace(taxInfo.BillingAddressPostalCode))
+        {
+            var taxRateSearch = new TaxRate
+            {
+                Country = taxInfo.BillingAddressCountry,
+                PostalCode = taxInfo.BillingAddressPostalCode
+            };
+            var taxRates = await _taxRateRepository.GetByLocationAsync(taxRateSearch);
+
+            // should only be one tax rate per country/zip combo
+            var taxRate = taxRates.FirstOrDefault();
+            if (taxRate != null)
+            {
+                taxInfo.StripeTaxRateId = taxRate.Id;
+            }
+        }
+
         var subCreateOptions = new OrganizationPurchaseSubscriptionOptions(org, plan, taxInfo, additionalSeats, additionalStorageGb, premiumAccessAddon
         , additionalSmSeats, additionalServiceAccount);
 
@@ -153,7 +175,10 @@ public class StripePaymentService : IPaymentService
             subCreateOptions.AddExpand("latest_invoice.payment_intent");
             subCreateOptions.Customer = customer.Id;
 
-            subCreateOptions.AutomaticTax = new Stripe.SubscriptionAutomaticTaxOptions { Enabled = true };
+            if (pm5766AutomaticTaxIsEnabled)
+            {
+                subCreateOptions.AutomaticTax = new Stripe.SubscriptionAutomaticTaxOptions { Enabled = true };
+            }
 
             subscription = await _stripeAdapter.SubscriptionCreateAsync(subCreateOptions);
             if (subscription.Status == "incomplete" && subscription.LatestInvoice?.PaymentIntent != null)
@@ -236,11 +261,34 @@ public class StripePaymentService : IPaymentService
             throw new GatewayException("Could not find customer payment profile.");
         }
 
-        if (customer.Address is null &&
+        var pm5766AutomaticTaxIsEnabled = _featureService.IsEnabled(FeatureFlagKeys.PM5766AutomaticTax);
+        var taxInfo = upgrade.TaxInfo;
+
+        if (!pm5766AutomaticTaxIsEnabled &&
+            taxInfo != null &&
+            !string.IsNullOrWhiteSpace(taxInfo.BillingAddressCountry) &&
+            !string.IsNullOrWhiteSpace(taxInfo.BillingAddressPostalCode))
+        {
+            var taxRateSearch = new TaxRate
+            {
+                Country = taxInfo.BillingAddressCountry,
+                PostalCode = taxInfo.BillingAddressPostalCode
+            };
+            var taxRates = await _taxRateRepository.GetByLocationAsync(taxRateSearch);
+
+            // should only be one tax rate per country/zip combo
+            var taxRate = taxRates.FirstOrDefault();
+            if (taxRate != null)
+            {
+                taxInfo.StripeTaxRateId = taxRate.Id;
+            }
+        }
+
+        if (pm5766AutomaticTaxIsEnabled &&
             !string.IsNullOrEmpty(upgrade.TaxInfo?.BillingAddressCountry) &&
             !string.IsNullOrEmpty(upgrade.TaxInfo?.BillingAddressPostalCode))
         {
-            var addressOptions = new Stripe.AddressOptions
+            var addressOptions = new AddressOptions
             {
                 Country = upgrade.TaxInfo.BillingAddressCountry,
                 PostalCode = upgrade.TaxInfo.BillingAddressPostalCode,
@@ -250,17 +298,20 @@ public class StripePaymentService : IPaymentService
                 City = upgrade.TaxInfo.BillingAddressCity,
                 State = upgrade.TaxInfo.BillingAddressState,
             };
-            var customerUpdateOptions = new Stripe.CustomerUpdateOptions { Address = addressOptions };
+            var customerUpdateOptions = new CustomerUpdateOptions { Address = addressOptions };
             customerUpdateOptions.AddExpand("default_source");
             customerUpdateOptions.AddExpand("invoice_settings.default_payment_method");
             customer = await _stripeAdapter.CustomerUpdateAsync(org.GatewayCustomerId, customerUpdateOptions);
         }
 
-        var subCreateOptions = new OrganizationUpgradeSubscriptionOptions(customer.Id, org, plan, upgrade)
+        var subCreateOptions = new OrganizationUpgradeSubscriptionOptions(customer.Id, org, plan, upgrade);
+
+        if (pm5766AutomaticTaxIsEnabled)
         {
-            DefaultTaxRates = new List<string>(),
-            AutomaticTax = new Stripe.SubscriptionAutomaticTaxOptions { Enabled = true }
-        };
+            subCreateOptions.DefaultTaxRates = new List<string>();
+            subCreateOptions.AutomaticTax = new SubscriptionAutomaticTaxOptions { Enabled = true };
+        }
+
         var (stripePaymentMethod, paymentMethodType) = IdentifyPaymentMethod(customer, subCreateOptions);
 
         var subscription = await ChargeForNewSubscriptionAsync(org, customer, false,
@@ -457,6 +508,29 @@ public class StripePaymentService : IPaymentService
             Quantity = 1
         });
 
+        var pm5766AutomaticTaxIsEnabled = _featureService.IsEnabled(FeatureFlagKeys.PM5766AutomaticTax);
+
+        if (!pm5766AutomaticTaxIsEnabled &&
+            !string.IsNullOrWhiteSpace(taxInfo?.BillingAddressCountry) &&
+            !string.IsNullOrWhiteSpace(taxInfo?.BillingAddressPostalCode))
+        {
+            var taxRates = await _taxRateRepository.GetByLocationAsync(
+                new TaxRate
+                {
+                    Country = taxInfo.BillingAddressCountry,
+                    PostalCode = taxInfo.BillingAddressPostalCode
+                }
+            );
+            var taxRate = taxRates.FirstOrDefault();
+            if (taxRate != null)
+            {
+                subCreateOptions.DefaultTaxRates = new List<string>(1)
+                {
+                    taxRate.Id
+                };
+            }
+        }
+
         if (additionalStorageGb > 0)
         {
             subCreateOptions.Items.Add(new Stripe.SubscriptionItemOptions
@@ -466,7 +540,11 @@ public class StripePaymentService : IPaymentService
             });
         }
 
-        subCreateOptions.AutomaticTax = new Stripe.SubscriptionAutomaticTaxOptions { Enabled = true };
+        if (pm5766AutomaticTaxIsEnabled)
+        {
+            subCreateOptions.DefaultTaxRates = new List<string>();
+            subCreateOptions.AutomaticTax = new SubscriptionAutomaticTaxOptions { Enabled = true };
+        }
 
         var subscription = await ChargeForNewSubscriptionAsync(user, customer, createdStripeCustomer,
             stripePaymentMethod, paymentMethodType, subCreateOptions, braintreeCustomer);
@@ -504,11 +582,14 @@ public class StripePaymentService : IPaymentService
                 var previewInvoice = await _stripeAdapter.InvoiceUpcomingAsync(new Stripe.UpcomingInvoiceOptions
                 {
                     Customer = customer.Id,
-                    SubscriptionItems = ToInvoiceSubscriptionItemOptions(subCreateOptions.Items),
-                    AutomaticTax =
-                        new Stripe.InvoiceAutomaticTaxOptions { Enabled = subCreateOptions.AutomaticTax.Enabled }
+                    SubscriptionItems = ToInvoiceSubscriptionItemOptions(subCreateOptions.Items)
                 });
 
+                if (_featureService.IsEnabled(FeatureFlagKeys.PM5766AutomaticTax))
+                {
+                    previewInvoice.AutomaticTax = new InvoiceAutomaticTax { Enabled = true };
+                }
+
                 if (previewInvoice.AmountDue > 0)
                 {
                     var braintreeCustomerId = customer.Metadata != null &&
@@ -560,13 +641,22 @@ public class StripePaymentService : IPaymentService
             }
             else if (paymentMethodType == PaymentMethodType.Credit)
             {
-                var previewInvoice = await _stripeAdapter.InvoiceUpcomingAsync(new Stripe.UpcomingInvoiceOptions
+                var upcomingInvoiceOptions = new UpcomingInvoiceOptions
                 {
                     Customer = customer.Id,
                     SubscriptionItems = ToInvoiceSubscriptionItemOptions(subCreateOptions.Items),
-                    AutomaticTax =
-                        new Stripe.InvoiceAutomaticTaxOptions { Enabled = subCreateOptions.AutomaticTax.Enabled }
-                });
+                    SubscriptionDefaultTaxRates = subCreateOptions.DefaultTaxRates,
+                };
+
+                var pm5766AutomaticTaxIsEnabled = _featureService.IsEnabled(FeatureFlagKeys.PM5766AutomaticTax);
+                if (pm5766AutomaticTaxIsEnabled)
+                {
+                    upcomingInvoiceOptions.AutomaticTax = new InvoiceAutomaticTaxOptions { Enabled = true };
+                    upcomingInvoiceOptions.SubscriptionDefaultTaxRates = new List<string>();
+                }
+
+                var previewInvoice = await _stripeAdapter.InvoiceUpcomingAsync(upcomingInvoiceOptions);
+
                 if (previewInvoice.AmountDue > 0)
                 {
                     throw new GatewayException("Your account does not have enough credit available.");
@@ -575,7 +665,12 @@ public class StripePaymentService : IPaymentService
 
             subCreateOptions.OffSession = true;
             subCreateOptions.AddExpand("latest_invoice.payment_intent");
-            subCreateOptions.AutomaticTax = new Stripe.SubscriptionAutomaticTaxOptions { Enabled = true };
+
+            if (_featureService.IsEnabled(FeatureFlagKeys.PM5766AutomaticTax))
+            {
+                subCreateOptions.AutomaticTax = new SubscriptionAutomaticTaxOptions { Enabled = true };
+            }
+
             subscription = await _stripeAdapter.SubscriptionCreateAsync(subCreateOptions);
             if (subscription.Status == "incomplete" && subscription.LatestInvoice?.PaymentIntent != null)
             {
@@ -675,16 +770,41 @@ public class StripePaymentService : IPaymentService
             DaysUntilDue = daysUntilDue ?? 1,
             CollectionMethod = "send_invoice",
             ProrationDate = prorationDate,
-            DefaultTaxRates = new List<string>(),
-            AutomaticTax = new Stripe.SubscriptionAutomaticTaxOptions { Enabled = true }
         };
 
+        var pm5766AutomaticTaxIsEnabled = _featureService.IsEnabled(FeatureFlagKeys.PM5766AutomaticTax);
+        if (pm5766AutomaticTaxIsEnabled)
+        {
+            subUpdateOptions.DefaultTaxRates = new List<string>();
+            subUpdateOptions.AutomaticTax = new SubscriptionAutomaticTaxOptions { Enabled = true };
+        }
+
         if (!subscriptionUpdate.UpdateNeeded(sub))
         {
             // No need to update subscription, quantity matches
             return null;
         }
 
+        if (!pm5766AutomaticTaxIsEnabled)
+        {
+            var customer = await _stripeAdapter.CustomerGetAsync(sub.CustomerId);
+
+            if (!string.IsNullOrWhiteSpace(customer?.Address?.Country)
+                && !string.IsNullOrWhiteSpace(customer?.Address?.PostalCode))
+            {
+                var taxRates = await _taxRateRepository.GetByLocationAsync(new TaxRate
+                {
+                    Country = customer.Address.Country,
+                    PostalCode = customer.Address.PostalCode
+                });
+                var taxRate = taxRates.FirstOrDefault();
+                if (taxRate != null && !sub.DefaultTaxRates.Any(x => x.Equals(taxRate.Id)))
+                {
+                    subUpdateOptions.DefaultTaxRates = new List<string>(1) { taxRate.Id };
+                }
+            }
+        }
+
         string paymentIntentClientSecret = null;
         try
         {

src/SharedWeb/Utilities/ServiceCollectionExtensions.cs

@@ -214,7 +214,7 @@ public static class ServiceCollectionExtensions
                 PrivateKey = globalSettings.Braintree.PrivateKey
             };
         });
-        services.AddSingleton<IPaymentService, StripePaymentService>();
+        services.AddScoped<IPaymentService, StripePaymentService>();
         services.AddSingleton<IStripeSyncService, StripeSyncService>();
         services.AddSingleton<IMailService, HandlebarsMailService>();
         services.AddSingleton<ILicensingService, LicensingService>();

test/Core.Test/Services/StripePaymentServiceTests.cs

@@ -701,6 +701,7 @@ public class StripePaymentServiceTests
     {
         organization.GatewaySubscriptionId = null;
         var stripeAdapter = sutProvider.GetDependency<IStripeAdapter>();
+        var featureService = sutProvider.GetDependency<IFeatureService>();
         stripeAdapter.CustomerGetAsync(default).ReturnsForAnyArgs(new Stripe.Customer
         {
             Id = "C-1",
@@ -723,6 +724,7 @@ public class StripePaymentServiceTests
             AmountDue = 0
         });
         stripeAdapter.SubscriptionCreateAsync(default).ReturnsForAnyArgs(new Stripe.Subscription { });
+        featureService.IsEnabled(FeatureFlagKeys.PM5766AutomaticTax).Returns(true);
 
         var upgrade = new OrganizationUpgrade()
         {