From d330fd2082fc5b38bf8f8ee8551ac45ac79a2c92 Mon Sep 17 00:00:00 2001 From: Kyle Denney <4227399+kdenney@users.noreply.github.com> Date: Wed, 21 Jan 2026 16:43:06 -0600 Subject: [PATCH] updated proration preview and upgrade to be consistent also using the correct proration behavior and making the upgrade flow start a trial --- .../Controllers/PreviewInvoiceController.cs | 4 +- .../UpgradePremiumToOrganizationRequest.cs | 34 +++--- .../PreviewPremiumUpgradeProrationRequest.cs | 25 +++- .../PreviewPremiumUpgradeProrationCommand.cs | 22 +--- .../UpgradePremiumToOrganizationCommand.cs | 9 +- ...viewPremiumUpgradeProrationRequestTests.cs | 56 +++++++++ ...pgradePremiumToOrganizationRequestTests.cs | 60 ++++++++++ ...viewPremiumUpgradeProrationCommandTests.cs | 113 ++---------------- ...pgradePremiumToOrganizationCommandTests.cs | 83 ++++++++++++- 9 files changed, 259 insertions(+), 147 deletions(-) create mode 100644 test/Api.Test/Billing/Models/Requests/PreviewPremiumUpgradeProrationRequestTests.cs create mode 100644 test/Api.Test/Billing/Models/Requests/UpgradePremiumToOrganizationRequestTests.cs diff --git a/src/Api/Billing/Controllers/PreviewInvoiceController.cs b/src/Api/Billing/Controllers/PreviewInvoiceController.cs index d55e7299d6..b2e2dcbad9 100644 --- a/src/Api/Billing/Controllers/PreviewInvoiceController.cs +++ b/src/Api/Billing/Controllers/PreviewInvoiceController.cs @@ -63,11 +63,11 @@ public class PreviewInvoiceController( [BindNever] User user, [FromBody] PreviewPremiumUpgradeProrationRequest request) { - var (tierType, billingAddress) = request.ToDomain(); + var (planType, billingAddress) = request.ToDomain(); var result = await previewPremiumUpgradeProrationCommand.Run( user, - tierType, + planType, billingAddress); return Handle(result.Map(pair => new { pair.Tax, pair.Total, pair.Credit })); diff --git a/src/Api/Billing/Models/Requests/Premium/UpgradePremiumToOrganizationRequest.cs b/src/Api/Billing/Models/Requests/Premium/UpgradePremiumToOrganizationRequest.cs index 14375efc78..7e7bf3ef3a 100644 --- a/src/Api/Billing/Models/Requests/Premium/UpgradePremiumToOrganizationRequest.cs +++ b/src/Api/Billing/Models/Requests/Premium/UpgradePremiumToOrganizationRequest.cs @@ -1,5 +1,6 @@ using System.ComponentModel.DataAnnotations; using System.Text.Json.Serialization; +using Bit.Api.Billing.Models.Requests.Payment; using Bit.Core.Billing.Enums; namespace Bit.Api.Billing.Models.Requests.Premium; @@ -14,24 +15,29 @@ public class UpgradePremiumToOrganizationRequest [Required] [JsonConverter(typeof(JsonStringEnumConverter))] - public ProductTierType Tier { get; set; } + public required ProductTierType TargetProductTierType { get; set; } [Required] - [JsonConverter(typeof(JsonStringEnumConverter))] - public PlanCadenceType Cadence { get; set; } + public required MinimalBillingAddressRequest BillingAddress { get; set; } - private PlanType PlanType => - Tier switch + private PlanType PlanType + { + get { - ProductTierType.Families => PlanType.FamiliesAnnually, - ProductTierType.Teams => Cadence == PlanCadenceType.Monthly - ? PlanType.TeamsMonthly - : PlanType.TeamsAnnually, - ProductTierType.Enterprise => Cadence == PlanCadenceType.Monthly - ? PlanType.EnterpriseMonthly - : PlanType.EnterpriseAnnually, - _ => throw new InvalidOperationException("Cannot upgrade to an Organization subscription that isn't Families, Teams or Enterprise.") - }; + if (TargetProductTierType is not (ProductTierType.Families or ProductTierType.Teams or ProductTierType.Enterprise)) + { + throw new InvalidOperationException($"Cannot upgrade Premium subscription to {TargetProductTierType} plan."); + } + + return TargetProductTierType switch + { + ProductTierType.Families => PlanType.FamiliesAnnually, + ProductTierType.Teams => PlanType.TeamsAnnually, + ProductTierType.Enterprise => PlanType.EnterpriseAnnually, + _ => throw new InvalidOperationException($"Unexpected ProductTierType: {TargetProductTierType}") + }; + } + } public (string OrganizationName, string Key, PlanType PlanType) ToDomain() => (OrganizationName, Key, PlanType); } diff --git a/src/Api/Billing/Models/Requests/PreviewInvoice/PreviewPremiumUpgradeProrationRequest.cs b/src/Api/Billing/Models/Requests/PreviewInvoice/PreviewPremiumUpgradeProrationRequest.cs index e3c109a155..68d7a8d002 100644 --- a/src/Api/Billing/Models/Requests/PreviewInvoice/PreviewPremiumUpgradeProrationRequest.cs +++ b/src/Api/Billing/Models/Requests/PreviewInvoice/PreviewPremiumUpgradeProrationRequest.cs @@ -1,4 +1,5 @@ using System.ComponentModel.DataAnnotations; +using System.Text.Json.Serialization; using Bit.Api.Billing.Models.Requests.Payment; using Bit.Core.Billing.Enums; using Bit.Core.Billing.Payment.Models; @@ -8,11 +9,31 @@ namespace Bit.Api.Billing.Models.Requests.PreviewInvoice; public record PreviewPremiumUpgradeProrationRequest { [Required] + [JsonConverter(typeof(JsonStringEnumConverter))] public required ProductTierType TargetProductTierType { get; set; } [Required] public required MinimalBillingAddressRequest BillingAddress { get; set; } - public (ProductTierType, BillingAddress) ToDomain() => - (TargetProductTierType, BillingAddress.ToDomain()); + private PlanType PlanType + { + get + { + if (TargetProductTierType is not (ProductTierType.Families or ProductTierType.Teams or ProductTierType.Enterprise)) + { + throw new InvalidOperationException($"Cannot upgrade Premium subscription to {TargetProductTierType} plan."); + } + + return TargetProductTierType switch + { + ProductTierType.Families => PlanType.FamiliesAnnually, + ProductTierType.Teams => PlanType.TeamsAnnually, + ProductTierType.Enterprise => PlanType.EnterpriseAnnually, + _ => throw new InvalidOperationException($"Unexpected ProductTierType: {TargetProductTierType}") + }; + } + } + + public (PlanType, BillingAddress) ToDomain() => + (PlanType, BillingAddress.ToDomain()); } diff --git a/src/Core/Billing/Premium/Commands/PreviewPremiumUpgradeProrationCommand.cs b/src/Core/Billing/Premium/Commands/PreviewPremiumUpgradeProrationCommand.cs index db5b907f8c..4c864677df 100644 --- a/src/Core/Billing/Premium/Commands/PreviewPremiumUpgradeProrationCommand.cs +++ b/src/Core/Billing/Premium/Commands/PreviewPremiumUpgradeProrationCommand.cs @@ -20,12 +20,12 @@ public interface IPreviewPremiumUpgradeProrationCommand /// Calculates the tax, total cost, and proration credit for upgrading a Premium subscription to an Organization plan. /// /// The user with an active Premium subscription. - /// The target organization tier (Families, Teams, or Enterprise). + /// The target organization plan type. /// The billing address for tax calculation. /// A tuple containing the tax amount, total cost, and proration credit from unused Premium time. Task> Run( User user, - ProductTierType targetProductTierType, + PlanType targetPlanType, BillingAddress billingAddress); } @@ -38,7 +38,7 @@ public class PreviewPremiumUpgradeProrationCommand( { public Task> Run( User user, - ProductTierType targetProductTierType, + PlanType targetPlanType, BillingAddress billingAddress) => HandleAsync<(decimal, decimal, decimal)>(async () => { if (user is not { Premium: true, GatewaySubscriptionId: not null and not "" }) @@ -46,20 +46,6 @@ public class PreviewPremiumUpgradeProrationCommand( return new BadRequest("User does not have an active Premium subscription."); } - if (targetProductTierType is not (ProductTierType.Families or ProductTierType.Teams or ProductTierType.Enterprise)) - { - return new BadRequest($"Cannot upgrade Premium subscription to {targetProductTierType} plan."); - } - - // Convert ProductTierType to PlanType (for premium upgrade, the only choice is annual plans so we can assume that cadence) - var targetPlanType = targetProductTierType switch - { - ProductTierType.Families => PlanType.FamiliesAnnually, - ProductTierType.Teams => PlanType.TeamsAnnually, - ProductTierType.Enterprise => PlanType.EnterpriseAnnually, - _ => throw new InvalidOperationException($"Unexpected ProductTierType: {targetProductTierType}") - }; - // Hardcode seats to 1 for upgrade flow const int seats = 1; @@ -128,7 +114,7 @@ public class PreviewPremiumUpgradeProrationCommand( SubscriptionDetails = new InvoiceSubscriptionDetailsOptions { Items = subscriptionItems, - ProrationBehavior = StripeConstants.ProrationBehavior.AlwaysInvoice + ProrationBehavior = StripeConstants.ProrationBehavior.CreateProrations } }; diff --git a/src/Core/Billing/Premium/Commands/UpgradePremiumToOrganizationCommand.cs b/src/Core/Billing/Premium/Commands/UpgradePremiumToOrganizationCommand.cs index 81bc5c9e2c..50f90808e2 100644 --- a/src/Core/Billing/Premium/Commands/UpgradePremiumToOrganizationCommand.cs +++ b/src/Core/Billing/Premium/Commands/UpgradePremiumToOrganizationCommand.cs @@ -74,7 +74,7 @@ public class UpgradePremiumToOrganizationCommand( if (passwordManagerItem == null) { - return new BadRequest("Premium subscription item not found."); + return new BadRequest("Premium subscription password manager item not found."); } var usersPremiumPlan = premiumPlans.First(p => p.Seat.StripePriceId == passwordManagerItem.Price.Id); @@ -133,7 +133,7 @@ public class UpgradePremiumToOrganizationCommand( var subscriptionUpdateOptions = new SubscriptionUpdateOptions { Items = subscriptionItemOptions, - ProrationBehavior = StripeConstants.ProrationBehavior.None, + ProrationBehavior = StripeConstants.ProrationBehavior.CreateProrations, Metadata = new Dictionary { [StripeConstants.MetadataKeys.OrganizationId] = organizationId.ToString(), @@ -145,6 +145,11 @@ public class UpgradePremiumToOrganizationCommand( } }; + if (targetPlan.TrialPeriodDays.HasValue) + { + subscriptionUpdateOptions.TrialEnd = DateTime.UtcNow.AddDays((double)targetPlan.TrialPeriodDays); + } + // Create the Organization entity var organization = new Organization { diff --git a/test/Api.Test/Billing/Models/Requests/PreviewPremiumUpgradeProrationRequestTests.cs b/test/Api.Test/Billing/Models/Requests/PreviewPremiumUpgradeProrationRequestTests.cs new file mode 100644 index 0000000000..5ed4182a5d --- /dev/null +++ b/test/Api.Test/Billing/Models/Requests/PreviewPremiumUpgradeProrationRequestTests.cs @@ -0,0 +1,56 @@ +using Bit.Api.Billing.Models.Requests.Payment; +using Bit.Api.Billing.Models.Requests.PreviewInvoice; +using Bit.Core.Billing.Enums; +using Xunit; + +namespace Bit.Api.Test.Billing.Models.Requests; + +public class PreviewPremiumUpgradeProrationRequestTests +{ + [Theory] + [InlineData(ProductTierType.Families, PlanType.FamiliesAnnually)] + [InlineData(ProductTierType.Teams, PlanType.TeamsAnnually)] + [InlineData(ProductTierType.Enterprise, PlanType.EnterpriseAnnually)] + public void ToDomain_ValidTierTypes_ReturnsPlanType(ProductTierType tierType, PlanType expectedPlanType) + { + // Arrange + var sut = new PreviewPremiumUpgradeProrationRequest + { + TargetProductTierType = tierType, + BillingAddress = new MinimalBillingAddressRequest + { + Country = "US", + PostalCode = "12345" + } + }; + + // Act + var (planType, billingAddress) = sut.ToDomain(); + + // Assert + Assert.Equal(expectedPlanType, planType); + Assert.Equal("US", billingAddress.Country); + Assert.Equal("12345", billingAddress.PostalCode); + } + + [Theory] + [InlineData(ProductTierType.Free)] + [InlineData(ProductTierType.TeamsStarter)] + public void ToDomain_InvalidTierTypes_ThrowsInvalidOperationException(ProductTierType tierType) + { + // Arrange + var sut = new PreviewPremiumUpgradeProrationRequest + { + TargetProductTierType = tierType, + BillingAddress = new MinimalBillingAddressRequest + { + Country = "US", + PostalCode = "12345" + } + }; + + // Act & Assert + var exception = Assert.Throws(() => sut.ToDomain()); + Assert.Contains($"Cannot upgrade Premium subscription to {tierType} plan", exception.Message); + } +} diff --git a/test/Api.Test/Billing/Models/Requests/UpgradePremiumToOrganizationRequestTests.cs b/test/Api.Test/Billing/Models/Requests/UpgradePremiumToOrganizationRequestTests.cs new file mode 100644 index 0000000000..6a8e328bf3 --- /dev/null +++ b/test/Api.Test/Billing/Models/Requests/UpgradePremiumToOrganizationRequestTests.cs @@ -0,0 +1,60 @@ +using Bit.Api.Billing.Models.Requests.Payment; +using Bit.Api.Billing.Models.Requests.Premium; +using Bit.Core.Billing.Enums; +using Xunit; + +namespace Bit.Api.Test.Billing.Models.Requests; + +public class UpgradePremiumToOrganizationRequestTests +{ + [Theory] + [InlineData(ProductTierType.Families, PlanType.FamiliesAnnually)] + [InlineData(ProductTierType.Teams, PlanType.TeamsAnnually)] + [InlineData(ProductTierType.Enterprise, PlanType.EnterpriseAnnually)] + public void ToDomain_ValidTierTypes_ReturnsPlanType(ProductTierType tierType, PlanType expectedPlanType) + { + // Arrange + var sut = new UpgradePremiumToOrganizationRequest + { + OrganizationName = "Test Organization", + Key = "encrypted-key", + TargetProductTierType = tierType, + BillingAddress = new MinimalBillingAddressRequest + { + Country = "US", + PostalCode = "12345" + } + }; + + // Act + var (organizationName, key, planType) = sut.ToDomain(); + + // Assert + Assert.Equal("Test Organization", organizationName); + Assert.Equal("encrypted-key", key); + Assert.Equal(expectedPlanType, planType); + } + + [Theory] + [InlineData(ProductTierType.Free)] + [InlineData(ProductTierType.TeamsStarter)] + public void ToDomain_InvalidTierTypes_ThrowsInvalidOperationException(ProductTierType tierType) + { + // Arrange + var sut = new UpgradePremiumToOrganizationRequest + { + OrganizationName = "Test Organization", + Key = "encrypted-key", + TargetProductTierType = tierType, + BillingAddress = new MinimalBillingAddressRequest + { + Country = "US", + PostalCode = "12345" + } + }; + + // Act & Assert + var exception = Assert.Throws(() => sut.ToDomain()); + Assert.Contains($"Cannot upgrade Premium subscription to {tierType} plan", exception.Message); + } +} diff --git a/test/Core.Test/Billing/Premium/Commands/PreviewPremiumUpgradeProrationCommandTests.cs b/test/Core.Test/Billing/Premium/Commands/PreviewPremiumUpgradeProrationCommandTests.cs index a681797a82..475c458361 100644 --- a/test/Core.Test/Billing/Premium/Commands/PreviewPremiumUpgradeProrationCommandTests.cs +++ b/test/Core.Test/Billing/Premium/Commands/PreviewPremiumUpgradeProrationCommandTests.cs @@ -36,7 +36,7 @@ public class PreviewPremiumUpgradeProrationCommandTests user.Premium = false; // Act - var result = await _command.Run(user, ProductTierType.Teams, billingAddress); + var result = await _command.Run(user, PlanType.TeamsAnnually, billingAddress); // Assert Assert.True(result.IsT1); @@ -52,7 +52,7 @@ public class PreviewPremiumUpgradeProrationCommandTests user.GatewaySubscriptionId = null; // Act - var result = await _command.Run(user, ProductTierType.Teams, billingAddress); + var result = await _command.Run(user, PlanType.TeamsAnnually, billingAddress); // Assert Assert.True(result.IsT1); @@ -136,7 +136,7 @@ public class PreviewPremiumUpgradeProrationCommandTests .Returns(invoice); // Act - var result = await _command.Run(user, ProductTierType.Teams, billingAddress); + var result = await _command.Run(user, PlanType.TeamsAnnually, billingAddress); // Assert Assert.True(result.IsT0); @@ -212,7 +212,7 @@ public class PreviewPremiumUpgradeProrationCommandTests .Returns(invoice); // Act - var result = await _command.Run(user, ProductTierType.Teams, billingAddress); + var result = await _command.Run(user, PlanType.TeamsAnnually, billingAddress); // Assert Assert.True(result.IsT0); @@ -279,7 +279,7 @@ public class PreviewPremiumUpgradeProrationCommandTests .Returns(invoice); // Act - await _command.Run(user, ProductTierType.Teams, billingAddress); + await _command.Run(user, PlanType.TeamsAnnually, billingAddress); // Assert - Verify that the subscription item quantity is always 1 await _stripeAdapter.Received(1).CreateInvoicePreviewAsync( @@ -289,82 +289,6 @@ public class PreviewPremiumUpgradeProrationCommandTests item.Quantity == 1))); } - [Theory] - [InlineData(ProductTierType.Families, PlanType.FamiliesAnnually)] - [InlineData(ProductTierType.Teams, PlanType.TeamsAnnually)] - [InlineData(ProductTierType.Enterprise, PlanType.EnterpriseAnnually)] - public async Task Run_ProductTierTypeConversion_MapsToCorrectPlanType( - ProductTierType productTierType, - PlanType expectedPlanType) - { - // Arrange - var user = new User - { - Premium = true, - GatewaySubscriptionId = "sub_123", - GatewayCustomerId = "cus_123" - }; - var billingAddress = new BillingAddress - { - Country = "US", - PostalCode = "12345" - }; - - var premiumPlan = new PremiumPlan - { - Name = "Premium", - Available = true, - LegacyYear = null, - Seat = new Bit.Core.Billing.Pricing.Premium.Purchasable - { - StripePriceId = "premium-annually", - Price = 10m, - Provided = 1 - }, - Storage = new Bit.Core.Billing.Pricing.Premium.Purchasable - { - StripePriceId = "storage-gb-annually", - Price = 4m, - Provided = 1 - } - }; - var premiumPlans = new List { premiumPlan }; - - var currentSubscription = new Subscription - { - Id = "sub_123", - Customer = new Customer { Id = "cus_123", Discount = null }, - Items = new StripeList - { - Data = new List - { - new() { Id = "si_premium", Price = new Price { Id = "premium-annually" } } - } - } - }; - - var targetPlan = new TeamsPlan(isAnnual: true); - - var invoice = new Invoice - { - Total = 5000, - TotalTaxes = new List { new() { Amount = 500 } } - }; - - _pricingClient.ListPremiumPlans().Returns(premiumPlans); - _pricingClient.GetPlanOrThrow(expectedPlanType).Returns(targetPlan); - _stripeAdapter.GetSubscriptionAsync("sub_123", Arg.Any()) - .Returns(currentSubscription); - _stripeAdapter.CreateInvoicePreviewAsync(Arg.Any()) - .Returns(invoice); - - // Act - await _command.Run(user, productTierType, billingAddress); - - // Assert - Verify that the correct PlanType was used - await _pricingClient.Received(1).GetPlanOrThrow(expectedPlanType); - } - [Theory, BitAutoData] public async Task Run_ValidUpgrade_DeletesPremiumSubscriptionItems(User user, BillingAddress billingAddress) { @@ -423,7 +347,7 @@ public class PreviewPremiumUpgradeProrationCommandTests .Returns(invoice); // Act - await _command.Run(user, ProductTierType.Teams, billingAddress); + await _command.Run(user, PlanType.TeamsAnnually, billingAddress); // Assert - Verify both password manager and storage items are marked as deleted await _stripeAdapter.Received(1).CreateInvoicePreviewAsync( @@ -491,7 +415,7 @@ public class PreviewPremiumUpgradeProrationCommandTests .Returns(invoice); // Act - await _command.Run(user, ProductTierType.Families, billingAddress); + await _command.Run(user, PlanType.FamiliesAnnually, billingAddress); // Assert - Verify non-seat-based plan uses StripePlanId with quantity 1 await _stripeAdapter.Received(1).CreateInvoicePreviewAsync( @@ -560,7 +484,7 @@ public class PreviewPremiumUpgradeProrationCommandTests .Returns(invoice); // Act - await _command.Run(user, ProductTierType.Teams, billingAddress); + await _command.Run(user, PlanType.TeamsAnnually, billingAddress); // Assert - Verify all invoice preview options are correct await _stripeAdapter.Received(1).CreateInvoicePreviewAsync( @@ -570,24 +494,7 @@ public class PreviewPremiumUpgradeProrationCommandTests options.Subscription == "sub_123" && options.CustomerDetails.Address.Country == "US" && options.CustomerDetails.Address.PostalCode == "12345" && - options.SubscriptionDetails.ProrationBehavior == "always_invoice")); - } - - [Theory, BitAutoData] - public async Task Run_TeamsStarterTierType_ReturnsBadRequest(User user, BillingAddress billingAddress) - { - // Arrange - user.Premium = true; - user.GatewaySubscriptionId = "sub_123"; - user.GatewayCustomerId = "cus_123"; - - // Act - var result = await _command.Run(user, ProductTierType.TeamsStarter, billingAddress); - - // Assert - Assert.True(result.IsT1); - var badRequest = result.AsT1; - Assert.Equal("Cannot upgrade Premium subscription to TeamsStarter plan.", badRequest.Response); + options.SubscriptionDetails.ProrationBehavior == "create_prorations")); } [Theory, BitAutoData] @@ -648,7 +555,7 @@ public class PreviewPremiumUpgradeProrationCommandTests .Returns(invoice); // Act - await _command.Run(user, ProductTierType.Teams, billingAddress); + await _command.Run(user, PlanType.TeamsAnnually, billingAddress); // Assert - Verify seat-based plan uses StripeSeatPlanId with quantity 1 await _stripeAdapter.Received(1).CreateInvoicePreviewAsync( diff --git a/test/Core.Test/Billing/Premium/Commands/UpgradePremiumToOrganizationCommandTests.cs b/test/Core.Test/Billing/Premium/Commands/UpgradePremiumToOrganizationCommandTests.cs index e686d04009..4ead5c12da 100644 --- a/test/Core.Test/Billing/Premium/Commands/UpgradePremiumToOrganizationCommandTests.cs +++ b/test/Core.Test/Billing/Premium/Commands/UpgradePremiumToOrganizationCommandTests.cs @@ -28,7 +28,8 @@ public class UpgradePremiumToOrganizationCommandTests string? stripePlanId = null, string? stripeSeatPlanId = null, string? stripePremiumAccessPlanId = null, - string? stripeStoragePlanId = null) + string? stripeStoragePlanId = null, + int? trialPeriodDays = null) { Type = planType; ProductTier = ProductTierType.Teams; @@ -37,7 +38,7 @@ public class UpgradePremiumToOrganizationCommandTests NameLocalizationKey = ""; DescriptionLocalizationKey = ""; CanBeUsedByBusiness = true; - TrialPeriodDays = null; + TrialPeriodDays = trialPeriodDays; HasSelfHost = false; HasPolicies = false; HasGroups = false; @@ -86,10 +87,9 @@ public class UpgradePremiumToOrganizationCommandTests string? stripePlanId = null, string? stripeSeatPlanId = null, string? stripePremiumAccessPlanId = null, - string? stripeStoragePlanId = null) - { - return new TestPlan(planType, stripePlanId, stripeSeatPlanId, stripePremiumAccessPlanId, stripeStoragePlanId); - } + string? stripeStoragePlanId = null, + int? trialPeriodDays = null) => + new TestPlan(planType, stripePlanId, stripeSeatPlanId, stripePremiumAccessPlanId, stripeStoragePlanId, trialPeriodDays); private static PremiumPlan CreateTestPremiumPlan( string seatPriceId = "premium-annually", @@ -643,4 +643,75 @@ public class UpgradePremiumToOrganizationCommandTests var badRequest = result.AsT1; Assert.Equal("Premium subscription item not found.", badRequest.Response); } + + [Theory, BitAutoData] + public async Task Run_PlanWithTrialPeriod_SetsTrialEnd(User user) + { + // Arrange + user.Premium = true; + user.GatewaySubscriptionId = "sub_123"; + user.GatewayCustomerId = "cus_123"; + + var currentPeriodEnd = DateTime.UtcNow.AddMonths(1); + var mockSubscription = new Subscription + { + Id = "sub_123", + Items = new StripeList + { + Data = new List + { + new SubscriptionItem + { + Id = "si_premium", + Price = new Price { Id = "premium-annually" }, + CurrentPeriodEnd = currentPeriodEnd + } + } + }, + Metadata = new Dictionary() + }; + + var mockPremiumPlans = CreateTestPremiumPlansList(); + + // Create a plan with a trial period + var mockPlan = CreateTestPlan( + PlanType.TeamsAnnually, + stripeSeatPlanId: "teams-seat-annually", + trialPeriodDays: 7 + ); + + // Capture the subscription update options to verify TrialEnd is set + SubscriptionUpdateOptions capturedOptions = null; + + _stripeAdapter.GetSubscriptionAsync("sub_123") + .Returns(mockSubscription); + _pricingClient.ListPremiumPlans().Returns(mockPremiumPlans); + _pricingClient.GetPlanOrThrow(PlanType.TeamsAnnually).Returns(mockPlan); + _stripeAdapter.UpdateSubscriptionAsync(Arg.Any(), Arg.Do(opts => capturedOptions = opts)) + .Returns(Task.FromResult(mockSubscription)); + _organizationRepository.CreateAsync(Arg.Any()).Returns(callInfo => Task.FromResult(callInfo.Arg())); + _organizationApiKeyRepository.CreateAsync(Arg.Any()).Returns(callInfo => Task.FromResult(callInfo.Arg())); + _organizationUserRepository.CreateAsync(Arg.Any()).Returns(callInfo => Task.FromResult(callInfo.Arg())); + _applicationCacheService.UpsertOrganizationAbilityAsync(Arg.Any()).Returns(Task.CompletedTask); + _userService.SaveUserAsync(user).Returns(Task.CompletedTask); + + // Act + var testStartTime = DateTime.UtcNow; + var result = await _command.Run(user, "My Organization", "encrypted-key", PlanType.TeamsAnnually); + var testEndTime = DateTime.UtcNow; + + // Assert + Assert.True(result.IsT0); + + await _stripeAdapter.Received(1).UpdateSubscriptionAsync("sub_123", Arg.Any()); + + Assert.NotNull(capturedOptions); + Assert.NotNull(capturedOptions.TrialEnd); + + // TrialEnd is AnyOf - verify it's a DateTime + var trialEndDateTime = capturedOptions.TrialEnd.Value as DateTime?; + Assert.NotNull(trialEndDateTime); + Assert.True(trialEndDateTime.Value >= testStartTime.AddDays(7)); + Assert.True(trialEndDateTime.Value <= testEndTime.AddDays(7)); + } }