[PM-38574] feat: Set trialInitiationPath for sales-assisted trials

src/Core/Billing/Constants/StripeConstants.cs

@@ -135,6 +135,16 @@ public static class CancellationOrigins
         public const string UnpaidSubscription = "unpaid_subscription";
     }
 
+    /// <summary>
+    /// The values carried in <see cref="MetadataKeys.TrialInitiationPath"/>.
+    /// </summary>
+    public static class TrialInitiationPaths
+    {
+        public const string MarketingInitiated = "marketing-initiated";
+        public const string ProductInitiated = "product-initiated";
+        public const string SalesAssisted = "sales-assisted";
+    }
+
     public static class PaymentBehavior
     {
         public const string DefaultIncomplete = "default_incomplete";

src/Core/Billing/Organizations/Models/OrganizationWarnings.cs

@@ -11,6 +11,7 @@ public record OrganizationWarnings
     public record FreeTrialWarning
     {
         public int RemainingTrialDays { get; set; }
+        public bool IsSalesAssisted { get; set; }
     }
 
     public record InactiveSubscriptionWarning

src/Core/Billing/Organizations/Queries/GetOrganizationWarningsQuery.cs

@@ -102,7 +102,12 @@ await subscriberService.GetSubscription(organization,
 
         var remainingTrialDays = (int)Math.Ceiling((subscription.TrialEnd.Value - now).TotalDays);
 
-        return new FreeTrialWarning { RemainingTrialDays = remainingTrialDays };
+        var isSalesAssisted = subscription.Metadata.TryGetValue(
+                                  StripeConstants.MetadataKeys.TrialInitiationPath,
+                                  out var trialInitiationPath) &&
+                              trialInitiationPath == StripeConstants.TrialInitiationPaths.SalesAssisted;
+
+        return new FreeTrialWarning { RemainingTrialDays = remainingTrialDays, IsSalesAssisted = isSalesAssisted };
     }
 
     private async Task<InactiveSubscriptionWarning?> GetInactiveSubscriptionWarningAsync(

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

@@ -35,6 +35,12 @@ public class OrganizationBillingService(
     ISubscriptionDiscountService subscriptionDiscountService,
     ITaxService taxService) : IOrganizationBillingService
 {
+    // Must match `InitiationPath.SalesAssistedTrialFromAdminPortal` in the clients repo.
+    private const string _salesAssistedTrialInitiationPath = "Sales assisted trial from admin portal";
+
+    // Matched as a substring of the client's `InitiationPath` marketing-trial values.
+    private const string _marketingTrialInitiationPathSegment = "trial from marketing website";
+
     public async Task Finalize(OrganizationSale sale)
     {
         var (organization, customerSetup, subscriptionSetup, owner) = sale;
@@ -452,11 +458,15 @@ private async Task<Subscription> CreateSubscriptionAsync(
             Items = subscriptionItemOptionsList,
             Metadata = new Dictionary<string, string>
             {
-                ["organizationId"] = organization.Id.ToString(),
-                ["trialInitiationPath"] = !string.IsNullOrEmpty(subscriptionSetup.InitiationPath) &&
-                                          subscriptionSetup.InitiationPath.Contains("trial from marketing website")
-                    ? "marketing-initiated"
-                    : "product-initiated"
+                [StripeConstants.MetadataKeys.OrganizationId] = organization.Id.ToString(),
+                [StripeConstants.MetadataKeys.TrialInitiationPath] = subscriptionSetup.InitiationPath switch
+                {
+                    var path when !string.IsNullOrEmpty(path) && path.Contains(_marketingTrialInitiationPathSegment)
+                        => StripeConstants.TrialInitiationPaths.MarketingInitiated,
+                    _salesAssistedTrialInitiationPath
+                        => StripeConstants.TrialInitiationPaths.SalesAssisted,
+                    _ => StripeConstants.TrialInitiationPaths.ProductInitiated
+                }
             },
             OffSession = true,
             TrialPeriodDays = subscriptionSetup.SkipTrial
@@ -499,6 +509,5 @@ private async Task<Subscription> CreateSubscriptionAsync(
         return subscription;
     }
 
-
     #endregion
 }

test/Core.Test/Billing/Organizations/Queries/GetOrganizationWarningsQueryTests.cs

@@ -74,6 +74,7 @@ public async Task Run_Has_FreeTrialWarning(
                     InvoiceSettings = new CustomerInvoiceSettings(),
                     Metadata = new Dictionary<string, string>()
                 },
+                Metadata = new Dictionary<string, string>(),
                 TestClock = new TestClock
                 {
                     FrozenTime = now
@@ -87,7 +88,48 @@ public async Task Run_Has_FreeTrialWarning(
 
         Assert.True(response is
         {
-            FreeTrial.RemainingTrialDays: 7
+            FreeTrial: { RemainingTrialDays: 7, IsSalesAssisted: false }
+        });
+    }
+
+    [Theory, BitAutoData]
+    public async Task Run_Has_FreeTrialWarning_SalesAssisted(
+        Organization organization,
+        SutProvider<GetOrganizationWarningsQuery> sutProvider)
+    {
+        var now = DateTime.UtcNow;
+
+        sutProvider.GetDependency<ISubscriberService>()
+            .GetSubscription(organization, Arg.Is<SubscriptionGetOptions>(options =>
+                options.Expand.SequenceEqual(_requiredExpansions)
+            ))
+            .Returns(new Subscription
+            {
+                Status = SubscriptionStatus.Trialing,
+                TrialEnd = now.AddDays(7),
+                Customer = new Customer
+                {
+                    InvoiceSettings = new CustomerInvoiceSettings(),
+                    Metadata = new Dictionary<string, string>()
+                },
+                Metadata = new Dictionary<string, string>
+                {
+                    [MetadataKeys.TrialInitiationPath] = TrialInitiationPaths.SalesAssisted
+                },
+                TestClock = new TestClock
+                {
+                    FrozenTime = now
+                }
+            });
+
+        sutProvider.GetDependency<ICurrentContext>().EditSubscription(organization.Id).Returns(true);
+        sutProvider.GetDependency<IHasPaymentMethodQuery>().Run(organization).Returns(false);
+
+        var response = await sutProvider.Sut.Run(organization);
+
+        Assert.True(response is
+        {
+            FreeTrial: { RemainingTrialDays: 7, IsSalesAssisted: true }
         });
     }
 

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

@@ -103,6 +103,88 @@ await sutProvider.GetDependency<IStripeAdapter>()
         Assert.Equal("cancel", capturedOptions.TrialSettings.EndBehavior.MissingPaymentMethod);
     }
 
+    // Literal strings on purpose: the initiation path sentence must match the clients-repo
+    // InitiationPath enum, and the metadata values are persisted in Stripe — changing either
+    // should fail this test.
+    [Theory]
+    [BitAutoData("Password Manager trial from marketing website", "marketing-initiated")]
+    [BitAutoData("Secrets Manager trial from marketing website", "marketing-initiated")]
+    [BitAutoData("Sales assisted trial from admin portal", "sales-assisted")]
+    [BitAutoData("New organization creation in-product", "product-initiated")]
+    [BitAutoData((string?)null, "product-initiated")]
+    public async Task Finalize_SetsTrialInitiationPathMetadata(
+        string? initiationPath,
+        string expectedMetadataValue,
+        Organization organization,
+        User owner,
+        SutProvider<OrganizationBillingService> sutProvider)
+    {
+        // Arrange
+        var plan = MockPlans.Get(PlanType.TeamsAnnually);
+        organization.PlanType = PlanType.TeamsAnnually;
+        organization.GatewayCustomerId = "cus_test123";
+        organization.GatewaySubscriptionId = null;
+
+        var subscriptionSetup = new SubscriptionSetup
+        {
+            PlanType = PlanType.TeamsAnnually,
+            PasswordManagerOptions = new SubscriptionSetup.PasswordManager
+            {
+                Seats = 5,
+                Storage = null,
+                PremiumAccess = false
+            },
+            SecretsManagerOptions = null,
+            SkipTrial = false,
+            InitiationPath = initiationPath
+        };
+
+        var sale = new OrganizationSale
+        {
+            Organization = organization,
+            SubscriptionSetup = subscriptionSetup,
+            Owner = owner
+        };
+
+        sutProvider.GetDependency<IPricingClient>()
+            .GetPlanOrThrow(PlanType.TeamsAnnually)
+            .Returns(plan);
+
+        sutProvider.GetDependency<IHasPaymentMethodQuery>()
+            .Run(organization)
+            .Returns(false);
+
+        var customer = new Customer
+        {
+            Id = "cus_test123",
+            Tax = new CustomerTax { AutomaticTax = StripeConstants.AutomaticTaxStatus.Supported }
+        };
+
+        sutProvider.GetDependency<ISubscriberService>()
+            .GetCustomerOrThrow(organization, Arg.Any<CustomerGetOptions>())
+            .Returns(customer);
+
+        SubscriptionCreateOptions capturedOptions = null;
+        sutProvider.GetDependency<IStripeAdapter>()
+            .CreateSubscriptionAsync(Arg.Do<SubscriptionCreateOptions>(options => capturedOptions = options))
+            .Returns(new Subscription
+            {
+                Id = "sub_test123",
+                Status = StripeConstants.SubscriptionStatus.Trialing
+            });
+
+        sutProvider.GetDependency<IOrganizationRepository>()
+            .ReplaceAsync(organization)
+            .Returns(Task.CompletedTask);
+
+        // Act
+        await sutProvider.Sut.Finalize(sale);
+
+        // Assert
+        Assert.NotNull(capturedOptions);
+        Assert.Equal(expectedMetadataValue, capturedOptions.Metadata["trialInitiationPath"]);
+    }
+
     [Theory, BitAutoData]
     public async Task NoPaymentMethodButNoTrial_DoesNotSetMissingPaymentMethodBehavior(
         Organization organization,