Handling of paddle purchases and add-ons.

AGENTS.md

@@ -141,6 +141,7 @@ private string searchQuery = string.Empty;
 - Wrap async operations in try-catch
 - Log errors via IWinoLogger
 - For dependency properties in WinUI code, always prefer `[GeneratedDependencyProperty]` from CommunityToolkit over manual `DependencyProperty.Register(...)` declarations.
+- When a `[RelayCommand]` needs enable/disable logic, prefer the command's `CanExecute` over binding `Button.IsEnabled` in XAML; use `[NotifyCanExecuteChangedFor]` on dependent properties and call `NotifyCanExecuteChanged()` explicitly when non-generated state affects the command.
 - In ViewModels, update all UI-bound properties/collections via `ExecuteUIThread(...)` (especially after awaited calls and any use of `ConfigureAwait(false)`).
 - ViewModels should only handle UI interaction/state and delegate business logic to services; account-management work belongs in `WinoAccountProfileService`, and preferences import/export/apply logic belongs in `PreferencesService`.
 - In `EventDetailsPageViewModel.LoadAttendeesAsync`, never mutate `CurrentEvent.Attendees` outside `ExecuteUIThread(...)`.

Wino.Core.Domain/Enums/WinoAddOnProductType.cs

@@ -0,0 +1,7 @@
+namespace Wino.Core.Domain.Enums;
+
+public enum WinoAddOnProductType
+{
+    AI_PACK,
+    UNLIMITED_ACCOUNTS
+}

Wino.Core.Domain/Interfaces/IStoreManagementService.cs

@@ -1,7 +1,5 @@
 using System.Threading.Tasks;
 using Wino.Core.Domain.Enums;
-using Wino.Core.Domain.Models.Store;
-
 namespace Wino.Core.Domain.Interfaces;
 
 public interface IStoreManagementService
@@ -9,10 +7,10 @@ public interface IStoreManagementService
     /// <summary>
     /// Checks whether user has the type of an add-on purchased.
     /// </summary>
-    Task<bool> HasProductAsync(StoreProductType productType);
+    Task<bool> HasProductAsync(WinoAddOnProductType productType);
 
     /// <summary>
     /// Attempts to purchase the given add-on.
     /// </summary>
-    Task<StorePurchaseResult> PurchaseAsync(StoreProductType productType);
+    Task<StorePurchaseResult> PurchaseAsync(WinoAddOnProductType productType);
 }

Wino.Core.Domain/Interfaces/IWinoAccountApiClient.cs

@@ -2,21 +2,25 @@
 using System.Text.Json;
 using System.Threading;
 using System.Threading.Tasks;
+using Wino.Core.Domain.Enums;
+using Wino.Core.Domain.Models.Accounts;
 using Wino.Mail.Api.Contracts.Ai;
 using Wino.Mail.Api.Contracts.Auth;
+using Wino.Mail.Api.Contracts.Billing;
 using Wino.Mail.Api.Contracts.Common;
 
 namespace Wino.Core.Domain.Interfaces;
 
 public interface IWinoAccountApiClient
 {
-    Task<ApiEnvelope<AuthResultDto>> RegisterAsync(string email, string password, CancellationToken cancellationToken = default);
+    Task<WinoAccountApiResult<AuthResultDto>> RegisterAsync(string email, string password, CancellationToken cancellationToken = default);
-    Task<ApiEnvelope<AuthResultDto>> LoginAsync(string email, string password, CancellationToken cancellationToken = default);
+    Task<WinoAccountApiResult<AuthResultDto>> LoginAsync(string email, string password, CancellationToken cancellationToken = default);
-    Task<ApiEnvelope<AuthResultDto>> RefreshAsync(string refreshToken, CancellationToken cancellationToken = default);
+    Task<WinoAccountApiResult<AuthResultDto>> RefreshAsync(string refreshToken, CancellationToken cancellationToken = default);
     Task<ApiEnvelope<JsonElement>> LogoutAsync(string refreshToken, CancellationToken cancellationToken = default);
     Task<ApiEnvelope<AuthUserDto>> GetCurrentUserAsync(CancellationToken cancellationToken = default);
     Task<ApiEnvelope<AiStatusResultDto>> GetAiStatusAsync(CancellationToken cancellationToken = default);
-    Task<ApiEnvelope<string>> CreateCheckoutSessionAsync(string productId, CancellationToken cancellationToken = default);
+    Task<ApiEnvelope<CheckoutSessionResultDto>> CreateCheckoutSessionAsync(WinoAddOnProductType productId, CancellationToken cancellationToken = default);
+    Task<ApiEnvelope<CustomerPortalResultDto>> CreateCustomerPortalSessionAsync(CancellationToken cancellationToken = default);
     Task<string?> GetSettingsAsync(CancellationToken cancellationToken = default);
     Task<bool> SaveSettingsAsync(string settingsJson, CancellationToken cancellationToken = default);
 }

Wino.Core.Domain/Interfaces/IWinoAccountProfileService.cs

@@ -2,9 +2,11 @@
 using System.Threading;
 using System.Threading.Tasks;
 using Wino.Core.Domain.Entities.Shared;
+using Wino.Core.Domain.Enums;
 using Wino.Core.Domain.Models.Accounts;
 using Wino.Mail.Api.Contracts.Ai;
 using Wino.Mail.Api.Contracts.Auth;
+using Wino.Mail.Api.Contracts.Billing;
 using Wino.Mail.Api.Contracts.Common;
 
 namespace Wino.Core.Domain.Interfaces;
@@ -17,8 +19,10 @@ public interface IWinoAccountProfileService
     Task<WinoAccount?> GetActiveAccountAsync();
     Task<WinoAccount?> GetAuthenticatedAccountAsync(CancellationToken cancellationToken = default);
     Task<bool> HasActiveAccountAsync();
+    Task<bool> HasAddOnAsync(WinoAddOnProductType productId, CancellationToken cancellationToken = default);
     Task<ApiEnvelope<AuthUserDto>> GetCurrentUserAsync(CancellationToken cancellationToken = default);
     Task<ApiEnvelope<AiStatusResultDto>> GetAiStatusAsync(CancellationToken cancellationToken = default);
-    Task<ApiEnvelope<string>> CreateCheckoutSessionAsync(string productId, CancellationToken cancellationToken = default);
+    Task<ApiEnvelope<CheckoutSessionResultDto>> CreateCheckoutSessionAsync(WinoAddOnProductType productId, CancellationToken cancellationToken = default);
+    Task<ApiEnvelope<CustomerPortalResultDto>> CreateCustomerPortalSessionAsync(CancellationToken cancellationToken = default);
     Task SignOutAsync(CancellationToken cancellationToken = default);
 }

Wino.Core.Domain/Interfaces/IWinoAddOnService.cs

@@ -0,0 +1,12 @@
+#nullable enable
+using System.Collections.Generic;
+using System.Threading;
+using System.Threading.Tasks;
+using Wino.Core.Domain.Models.Accounts;
+
+namespace Wino.Core.Domain.Interfaces;
+
+public interface IWinoAddOnService
+{
+    Task<IReadOnlyList<WinoAddOnInfo>> GetAvailableAddOnsAsync(CancellationToken cancellationToken = default);
+}

Wino.Core.Domain/Models/Accounts/WinoAccountApiResult.cs

@@ -0,0 +1,26 @@
+#nullable enable
+
+namespace Wino.Core.Domain.Models.Accounts;
+
+public sealed class WinoAccountApiResult<T>
+{
+    public bool IsSuccess { get; init; }
+    public string? ErrorCode { get; init; }
+    public string? ErrorMessage { get; init; }
+    public T? Result { get; init; }
+
+    public static WinoAccountApiResult<T> Success(T result)
+        => new()
+        {
+            IsSuccess = true,
+            Result = result
+        };
+
+    public static WinoAccountApiResult<T> Failure(string? errorCode, string? errorMessage = null)
+        => new()
+        {
+            IsSuccess = false,
+            ErrorCode = errorCode,
+            ErrorMessage = errorMessage
+        };
+}

Wino.Core.Domain/Models/Accounts/WinoAccountOperationResult.cs

@@ -7,6 +7,7 @@ public sealed class WinoAccountOperationResult
 {
     public bool IsSuccess { get; init; }
     public string? ErrorCode { get; init; }
+    public string? ErrorMessage { get; init; }
     public WinoAccount? Account { get; init; }
 
     public static WinoAccountOperationResult Success(WinoAccount account)
@@ -16,10 +17,11 @@ public sealed class WinoAccountOperationResult
             Account = account
         };
 
-    public static WinoAccountOperationResult Failure(string? errorCode)
+    public static WinoAccountOperationResult Failure(string? errorCode, string? errorMessage = null)
         => new()
         {
             IsSuccess = false,
-            ErrorCode = errorCode
+            ErrorCode = errorCode,
+            ErrorMessage = errorMessage
         };
 }

Wino.Core.Domain/Models/Accounts/WinoAddOnInfo.cs

@@ -0,0 +1,12 @@
+using System;
+using Wino.Core.Domain.Enums;
+
+namespace Wino.Core.Domain.Models.Accounts;
+
+public sealed record WinoAddOnInfo(
+    WinoAddOnProductType ProductType,
+    bool IsPurchased,
+    int? UsageCount = null,
+    int? UsageLimit = null,
+    double UsagePercentage = 0,
+    DateTimeOffset? RenewalDateUtc = null);

Wino.Core.Domain/Models/Store/StoreProductType.cs

@@ -1,6 +0,0 @@
-namespace Wino.Core.Domain.Models.Store;
-
-public enum StoreProductType
-{
-    UnlimitedAccounts
-}

Wino.Core.Domain/Translations/en_US/resources.json

@@ -84,6 +84,7 @@
     "Buttons_SyncAliases": "Synchronize Aliases",
     "Buttons_TryAgain": "Try Again",
     "Buttons_Yes": "Yes",
+    "Purchased": "Purchased",
     "Sync_SynchronizingFolder": "Synchronizing {0} {1}%",
     "Sync_DownloadedMessages": "Downloaded {0} messages from {1}",
     "SyncAction_Archiving": "Archiving {0} mail(s)",
@@ -860,7 +861,7 @@
     "WinoAccount_Management_SignedOutTitle": "Sign in to Wino Mail",
     "WinoAccount_Management_SignedOutDescription": "Sign in or create an account to sync your email, access AI features, and manage your settings across devices.",
     "WinoAccount_Management_ProfileSectionHeader": "Profile",
-    "WinoAccount_Management_AiPackSectionHeader": "AI Pack",
+    "WinoAccount_Management_AddOnsSectionHeader": "Wino Add-Ons",
     "WinoAccount_Management_DataSectionHeader": "Data",
     "WinoAccount_Management_AccountActionsSectionHeader": "Account actions",
     "WinoAccount_Management_AccountCardTitle": "Account",
@@ -887,14 +888,10 @@
     "WinoAccount_Management_AiPackFeatureTranslate": "Translate",
     "WinoAccount_Management_AiPackFeatureRewrite": "Rewrite",
     "WinoAccount_Management_AiPackFeatureSummarize": "Summarize",
-    "WinoAccount_Management_ImportSettingsTitle": "Import settings",
+    "WinoAccount_Management_SyncPreferencesTitle": "Synchronize Preferences",
-    "WinoAccount_Management_ImportSettingsDescription": "Restore your preferences from cloud.",
+    "WinoAccount_Management_SyncPreferencesDescription": "Import or export your preferences to cloud. Import them across devices.",
-    "WinoAccount_Management_ExportSettingsTitle": "Export settings",
-    "WinoAccount_Management_ExportSettingsDescription": "Save your preferences to cloud.",
     "WinoAccount_Management_SignOutTitle": "Sign out",
     "WinoAccount_Management_SignOutDescription": "Sign out of your account on this device",
-    "WinoAccount_Management_SettingsCardTitle": "Settings sync",
-    "WinoAccount_Management_SettingsCardDescription": "Export your current settings to your Wino Account or import them back on this device.",
     "WinoAccount_Management_StatusLabel": "Status: {0}",
     "WinoAccount_Management_NoRemoteSettings": "There are no synchronized settings stored for this account yet.",
     "WinoAccount_Management_ExportSucceeded": "Your settings were exported to your Wino Account.",
@@ -905,6 +902,12 @@
     "WinoAccount_Management_ImportEmpty": "The synchronized settings payload does not contain any values to restore.",
     "WinoAccount_Management_LoadFailed": "Wino could not load the latest Wino Account information.",
     "WinoAccount_Management_ActionFailed": "The Wino Account request could not be completed.",
+    "WinoAddOn_AI_PACK_Name": "AI Pack",
+    "WinoAddOn_AI_PACK_Description": "Translate, rewrite, and summarize emails with Wino AI.",
+    "WinoAddOn_AI_PACK_Keywords": "Translate · Rewrite · Summarize",
+    "WinoAddOn_UNLIMITED_ACCOUNTS_Name": "Unlimited Accounts",
+    "WinoAddOn_UNLIMITED_ACCOUNTS_Description": "Remove the 3-account limit and add as many accounts as you need.",
+    "WinoAddOn_UNLIMITED_ACCOUNTS_Keywords": "More accounts · No limit · One-time purchase",
     "SettingsSearch_MessageList_Keywords": "message;messages;list;threading;threads;avatar;preview;sender",
     "SettingsSearch_ReadComposePane_Keywords": "reader;compose;composer;font;fonts;external content;display;reading",
     "SettingsSearch_SignatureAndEncryption_Keywords": "signature;signatures;encryption;certificate;certificates;s mime;smime;security",

Wino.Core.Tests/Services/WinoAccountProfileServiceTests.cs

@@ -3,7 +3,9 @@ using System.Threading.Tasks;
 using FluentAssertions;
 using Moq;
 using Wino.Core.Domain.Entities.Shared;
+using Wino.Core.Domain.Enums;
 using Wino.Core.Domain.Interfaces;
+using Wino.Core.Domain.Models.Accounts;
 using Wino.Mail.Api.Contracts.Auth;
 using Wino.Mail.Api.Contracts.Common;
 using Wino.Services;
@@ -15,6 +17,7 @@ namespace Wino.Core.Tests.Services;
 public class WinoAccountProfileServiceTests : IAsyncLifetime
 {
     private readonly Mock<IWinoAccountApiClient> _apiClient = new();
+    private readonly Mock<IStoreManagementService> _storeManagementService = new();
     private InMemoryDatabaseService _databaseService = null!;
     private WinoAccountProfileService _service = null!;
 
@@ -22,7 +25,7 @@ public class WinoAccountProfileServiceTests : IAsyncLifetime
     {
         _databaseService = new InMemoryDatabaseService();
         await _databaseService.InitializeAsync();
-        _service = new WinoAccountProfileService(_databaseService, _apiClient.Object);
+        _service = new WinoAccountProfileService(_databaseService, _apiClient.Object, _storeManagementService.Object);
     }
 
     public async Task DisposeAsync()
@@ -37,7 +40,7 @@ public class WinoAccountProfileServiceTests : IAsyncLifetime
 
         _apiClient
             .Setup(x => x.LoginAsync("first@example.com", "pw", default))
-            .ReturnsAsync(ApiEnvelope<AuthResultDto>.Success(authResult));
+            .ReturnsAsync(WinoAccountApiResult<AuthResultDto>.Success(authResult));
 
         var result = await _service.LoginAsync("first@example.com", "pw");
 
@@ -56,11 +59,11 @@ public class WinoAccountProfileServiceTests : IAsyncLifetime
     {
         _apiClient
             .Setup(x => x.LoginAsync("first@example.com", "pw", default))
-            .ReturnsAsync(ApiEnvelope<AuthResultDto>.Success(CreateAuthResult("first@example.com")));
+            .ReturnsAsync(WinoAccountApiResult<AuthResultDto>.Success(CreateAuthResult("first@example.com")));
 
         _apiClient
             .Setup(x => x.LoginAsync("second@example.com", "pw", default))
-            .ReturnsAsync(ApiEnvelope<AuthResultDto>.Success(CreateAuthResult("second@example.com")));
+            .ReturnsAsync(WinoAccountApiResult<AuthResultDto>.Success(CreateAuthResult("second@example.com")));
 
         await _service.LoginAsync("first@example.com", "pw");
         await _service.LoginAsync("second@example.com", "pw");
@@ -77,7 +80,7 @@ public class WinoAccountProfileServiceTests : IAsyncLifetime
 
         _apiClient
             .Setup(x => x.LoginAsync("signout@example.com", "pw", default))
-            .ReturnsAsync(ApiEnvelope<AuthResultDto>.Success(authResult));
+            .ReturnsAsync(WinoAccountApiResult<AuthResultDto>.Success(authResult));
 
         _apiClient
             .Setup(x => x.LogoutAsync(authResult.RefreshToken, default))
@@ -90,6 +93,32 @@ public class WinoAccountProfileServiceTests : IAsyncLifetime
         persisted.Should().BeEmpty();
     }
 
+    [Fact]
+    public async Task HasAddOnAsync_ShouldUseLegacyStoreForUnlimitedAccounts()
+    {
+        _storeManagementService
+            .Setup(x => x.HasProductAsync(WinoAddOnProductType.UNLIMITED_ACCOUNTS))
+            .ReturnsAsync(true);
+
+        var hasAddOn = await _service.HasAddOnAsync(WinoAddOnProductType.UNLIMITED_ACCOUNTS);
+
+        hasAddOn.Should().BeTrue();
+    }
+
+    [Fact]
+    public async Task LoginAsync_ShouldPreserveEnvelopeErrorMessage()
+    {
+        _apiClient
+            .Setup(x => x.LoginAsync("first@example.com", "pw", default))
+            .ReturnsAsync(WinoAccountApiResult<AuthResultDto>.Failure(ApiErrorCodes.InvalidCredentials, "Password does not match this account."));
+
+        var result = await _service.LoginAsync("first@example.com", "pw");
+
+        result.IsSuccess.Should().BeFalse();
+        result.ErrorCode.Should().Be(ApiErrorCodes.InvalidCredentials);
+        result.ErrorMessage.Should().Be("Password does not match this account.");
+    }
+
     private static AuthResultDto CreateAuthResult(string email)
     {
         return new AuthResultDto(

Wino.Core.ViewModels/AccountManagementPageViewModelBase.cs

@@ -9,7 +9,6 @@ using Wino.Core.Domain.Entities.Shared;
 using Wino.Core.Domain.Enums;
 using Wino.Core.Domain.Interfaces;
 using Wino.Core.Domain.Models.Navigation;
-using Wino.Core.Domain.Models.Store;
 using Wino.Mail.ViewModels.Data;
 using Wino.Messaging.Client.Navigation;
 
@@ -44,6 +43,7 @@ public abstract partial class AccountManagementPageViewModelBase : CoreBaseViewM
     protected IAccountService AccountService { get; }
     protected IProviderService ProviderService { get; }
     protected IStoreManagementService StoreManagementService { get; }
+    protected IWinoAccountProfileService WinoAccountProfileService { get; }
     protected IAuthenticationProvider AuthenticationProvider { get; }
     protected IPreferencesService PreferencesService { get; }
 
@@ -52,6 +52,7 @@ public abstract partial class AccountManagementPageViewModelBase : CoreBaseViewM
                                               IAccountService accountService,
                                               IProviderService providerService,
                                               IStoreManagementService storeManagementService,
+                                              IWinoAccountProfileService winoAccountProfileService,
                                               IAuthenticationProvider authenticationProvider,
                                               IPreferencesService preferencesService)
     {
@@ -60,6 +61,7 @@ public abstract partial class AccountManagementPageViewModelBase : CoreBaseViewM
         AccountService = accountService;
         ProviderService = providerService;
         StoreManagementService = storeManagementService;
+        WinoAccountProfileService = winoAccountProfileService;
         AuthenticationProvider = authenticationProvider;
         PreferencesService = preferencesService;
     }
@@ -75,7 +77,7 @@ public abstract partial class AccountManagementPageViewModelBase : CoreBaseViewM
     [RelayCommand]
     public async Task PurchaseUnlimitedAccountAsync()
     {
-        var purchaseResult = await StoreManagementService.PurchaseAsync(StoreProductType.UnlimitedAccounts);
+        var purchaseResult = await StoreManagementService.PurchaseAsync(WinoAddOnProductType.UNLIMITED_ACCOUNTS);
 
         if (purchaseResult == StorePurchaseResult.Succeeded)
             DialogService.InfoBarMessage(Translator.Info_PurchaseThankYouTitle, Translator.Info_PurchaseThankYouMessage, InfoBarMessageType.Success);
@@ -92,14 +94,12 @@ public abstract partial class AccountManagementPageViewModelBase : CoreBaseViewM
 
     public async Task ManageStorePurchasesAsync()
     {
-        await ExecuteUIThread(async () =>
+        var hasUnlimitedAccountProduct = await WinoAccountProfileService.HasAddOnAsync(WinoAddOnProductType.UNLIMITED_ACCOUNTS).ConfigureAwait(false);
-        {
-            HasUnlimitedAccountProduct = await StoreManagementService.HasProductAsync(StoreProductType.UnlimitedAccounts);
 
-            if (!HasUnlimitedAccountProduct)
+        await ExecuteUIThread(() =>
-                IsAccountCreationBlocked = Accounts.Count >= FREE_ACCOUNT_COUNT;
+        {
-            else
+            HasUnlimitedAccountProduct = hasUnlimitedAccountProduct;
-                IsAccountCreationBlocked = false;
+            IsAccountCreationBlocked = !hasUnlimitedAccountProduct && Accounts.Count >= FREE_ACCOUNT_COUNT;
         });
     }
 

Wino.Core.ViewModels/Data/WinoAddOnItemViewModel.cs

@@ -0,0 +1,52 @@
+#nullable enable
+using CommunityToolkit.Mvvm.ComponentModel;
+using System.Windows.Input;
+using Wino.Core.Domain.Enums;
+
+namespace Wino.Core.ViewModels.Data;
+
+public partial class WinoAddOnItemViewModel : ObservableObject
+{
+    public WinoAddOnProductType ProductType { get; }
+
+    public string NameKey => $"WinoAddOn_{ProductType}_Name";
+    public string DescriptionKey => $"WinoAddOn_{ProductType}_Description";
+    public string KeywordsKey => $"WinoAddOn_{ProductType}_Keywords";
+
+    public string IconGlyph => ProductType switch
+    {
+        WinoAddOnProductType.AI_PACK => "\uE945",
+        WinoAddOnProductType.UNLIMITED_ACCOUNTS => "\uE716",
+        _ => "\uE10F"
+    };
+
+    [ObservableProperty]
+    public partial bool IsPurchased { get; set; }
+
+    public ICommand? PurchaseCommand { get; set; }
+
+    public ICommand? ManageCommand { get; set; }
+
+    [ObservableProperty]
+    public partial bool IsPurchaseInProgress { get; set; }
+
+    [ObservableProperty]
+    public partial int UsageCount { get; set; }
+
+    [ObservableProperty]
+    public partial int UsageLimit { get; set; } = 1;
+
+    [ObservableProperty]
+    public partial double UsagePercentage { get; set; }
+
+    [ObservableProperty]
+    public partial string RenewalText { get; set; } = string.Empty;
+
+    [ObservableProperty]
+    public partial string UsageResetText { get; set; } = string.Empty;
+
+    public WinoAddOnItemViewModel(WinoAddOnProductType productType)
+    {
+        ProductType = productType;
+    }
+}

Wino.Core.ViewModels/WinoAccountManagementPageViewModel.cs

@@ -1,17 +1,19 @@
 #nullable enable
 using System;
-using System.Globalization;
+using System.Collections.Generic;
+using System.Collections.ObjectModel;
+using System.Linq;
 using System.Threading.Tasks;
 using CommunityToolkit.Mvvm.ComponentModel;
 using CommunityToolkit.Mvvm.Input;
 using CommunityToolkit.Mvvm.Messaging;
 using Wino.Core.Domain;
-using Wino.Core.Domain.Entities.Shared;
 using Wino.Core.Domain.Enums;
 using Wino.Core.Domain.Interfaces;
+using Wino.Core.Domain.Models.Accounts;
 using Wino.Core.Domain.Models.Navigation;
-using Wino.Mail.Api.Contracts.Ai;
+using Wino.Mail.Api.Contracts.Billing;
-using Wino.Mail.Api.Contracts.Auth;
+using Wino.Core.ViewModels.Data;
 using Wino.Messaging.UI;
 
 namespace Wino.Core.ViewModels;
@@ -20,27 +22,20 @@ public partial class WinoAccountManagementPageViewModel : CoreBaseViewModel,
     IRecipient<WinoAccountSignedInMessage>,
     IRecipient<WinoAccountSignedOutMessage>
 {
-    private const string AiPackProductId = "ai-pack-monthly";
-    private const string ManageAiPackUrl = "https://example.com/wino-ai-pack/manage";
-
     private readonly IWinoAccountProfileService _profileService;
+    private readonly IWinoAddOnService _addOnService;
     private readonly IMailDialogService _dialogService;
     private readonly INativeAppService _nativeAppService;
 
+    public ObservableCollection<WinoAddOnItemViewModel> AddOns { get; } = [];
+
     [ObservableProperty]
     public partial bool IsBusy { get; set; }
 
     [ObservableProperty]
     [NotifyPropertyChangedFor(nameof(IsSignedOut))]
-    [NotifyPropertyChangedFor(nameof(CanShowBuyAiPack))]
     public partial bool IsSignedIn { get; set; }
 
-    [ObservableProperty]
-    public partial string AccountDisplayName { get; set; } = string.Empty;
-
-    [ObservableProperty]
-    public partial string AccountInitials { get; set; } = string.Empty;
-
     [ObservableProperty]
     public partial string AccountEmail { get; set; } = string.Empty;
 
@@ -48,48 +43,18 @@ public partial class WinoAccountManagementPageViewModel : CoreBaseViewModel,
     public partial string AccountStatusText { get; set; } = string.Empty;
 
     [ObservableProperty]
-    [NotifyPropertyChangedFor(nameof(CanShowAiUsage))]
+    [NotifyCanExecuteChangedFor(nameof(PurchaseAddOnCommand))]
-    [NotifyPropertyChangedFor(nameof(CanShowBuyAiPack))]
+    public partial bool IsCheckoutInProgress { get; set; }
-    public partial bool HasAiPack { get; set; }
-
-    [ObservableProperty]
-    public partial string AiPackStateText { get; set; } = Translator.WinoAccount_Management_AiPackInactive;
-
-    [ObservableProperty]
-    public partial string AiUsageSummary { get; set; } = string.Empty;
-
-    [ObservableProperty]
-    public partial string AiBillingPeriodSummary { get; set; } = string.Empty;
-
-    [ObservableProperty]
-    public partial string AiPackRenewalText { get; set; } = string.Empty;
-
-    [ObservableProperty]
-    public partial int AiUsageCount { get; set; }
-
-    [ObservableProperty]
-    public partial int AiUsageLimit { get; set; } = 1;
-
-    [ObservableProperty]
-    public partial double AiUsagePercentage { get; set; }
-
-    [ObservableProperty]
-    public partial string AiUsageResetText { get; set; } = string.Empty;
-
-    [ObservableProperty]
-    [NotifyPropertyChangedFor(nameof(CanBuyAiPack))]
-    public partial bool IsAiPackCheckoutInProgress { get; set; }
 
     public bool IsSignedOut => !IsSignedIn;
-    public bool CanShowAiUsage => HasAiPack;
-    public bool CanShowBuyAiPack => IsSignedIn && !HasAiPack;
-    public bool CanBuyAiPack => !IsAiPackCheckoutInProgress;
 
     public WinoAccountManagementPageViewModel(IWinoAccountProfileService profileService,
+                                              IWinoAddOnService addOnService,
                                               IMailDialogService dialogService,
                                               INativeAppService nativeAppService)
     {
         _profileService = profileService;
+        _addOnService = addOnService;
         _dialogService = dialogService;
         _nativeAppService = nativeAppService;
     }
@@ -147,16 +112,15 @@ public partial class WinoAccountManagementPageViewModel : CoreBaseViewModel,
                                       InfoBarMessageType.Success);
     }
 
-    [RelayCommand]
+    [RelayCommand(CanExecute = nameof(CanPurchaseAddOn))]
-    private async Task BuyAiPackAsync()
+    private async Task PurchaseAddOnAsync(WinoAddOnItemViewModel? addOn)
     {
-        if (IsAiPackCheckoutInProgress)
+        if (addOn == null)
         {
             return;
         }
 
         var account = await _profileService.GetAuthenticatedAccountAsync().ConfigureAwait(false);
-
         if (account == null)
         {
             _dialogService.InfoBarMessage(Translator.GeneralTitle_Warning,
@@ -165,13 +129,17 @@ public partial class WinoAccountManagementPageViewModel : CoreBaseViewModel,
             return;
         }
 
-        await ExecuteUIThread(() => IsAiPackCheckoutInProgress = true);
+        await ExecuteUIThread(() =>
+        {
+            IsCheckoutInProgress = true;
+            addOn.IsPurchaseInProgress = true;
+        });
 
         try
         {
-            var checkoutSession = await _profileService.CreateCheckoutSessionAsync(AiPackProductId).ConfigureAwait(false);
+            var checkoutSession = await _profileService.CreateCheckoutSessionAsync(addOn.ProductType).ConfigureAwait(false);
 
-            if (!checkoutSession.IsSuccess || string.IsNullOrWhiteSpace(checkoutSession.Result))
+            if (!checkoutSession.IsSuccess || string.IsNullOrWhiteSpace(checkoutSession.Result?.Url))
             {
                 _dialogService.InfoBarMessage(Translator.GeneralTitle_Error,
                                               Translator.WinoAccount_Management_PurchaseStartFailed,
@@ -179,8 +147,7 @@ public partial class WinoAccountManagementPageViewModel : CoreBaseViewModel,
                 return;
             }
 
-            var isLaunched = await _nativeAppService.LaunchUriAsync(new Uri(checkoutSession.Result)).ConfigureAwait(false);
+            var isLaunched = await _nativeAppService.LaunchUriAsync(new Uri(checkoutSession.Result.Url)).ConfigureAwait(false);
-
             if (!isLaunched)
             {
                 _dialogService.InfoBarMessage(Translator.GeneralTitle_Error,
@@ -199,12 +166,49 @@ public partial class WinoAccountManagementPageViewModel : CoreBaseViewModel,
         }
         finally
         {
-            await ExecuteUIThread(() => IsAiPackCheckoutInProgress = false);
+            await ExecuteUIThread(() =>
+            {
+                IsCheckoutInProgress = false;
+                addOn.IsPurchaseInProgress = false;
+            });
         }
     }
 
+    private bool CanPurchaseAddOn(WinoAddOnItemViewModel? addOn)
+        => addOn != null && !addOn.IsPurchased && !IsCheckoutInProgress;
+
     [RelayCommand]
-    private async Task ManageAiPackAsync() => await _nativeAppService.LaunchUriAsync(new Uri(ManageAiPackUrl));
+    private async Task ManageAiPackAsync()
+    {
+        try
+        {
+            var portalSession = await _profileService.CreateCustomerPortalSessionAsync().ConfigureAwait(false);
+            if (!portalSession.IsSuccess || string.IsNullOrWhiteSpace(portalSession.Result?.Url))
+            {
+                _dialogService.InfoBarMessage(Translator.GeneralTitle_Error,
+                                              Translator.WinoAccount_Management_PurchaseStartFailed,
+                                              InfoBarMessageType.Error);
+                return;
+            }
+
+            var isLaunched = await _nativeAppService.LaunchUriAsync(new Uri(portalSession.Result.Url)).ConfigureAwait(false);
+            if (!isLaunched)
+            {
+                _dialogService.InfoBarMessage(Translator.GeneralTitle_Error,
+                                              Translator.WinoAccount_Management_PurchaseStartFailed,
+                                              InfoBarMessageType.Error);
+            }
+        }
+        catch (OperationCanceledException)
+        {
+        }
+        catch (Exception)
+        {
+            _dialogService.InfoBarMessage(Translator.GeneralTitle_Error,
+                                          Translator.WinoAccount_Management_PurchaseStartFailed,
+                                          InfoBarMessageType.Error);
+        }
+    }
 
     [RelayCommand]
     private Task ExportSettingsAsync() => Task.CompletedTask;
@@ -232,7 +236,7 @@ public partial class WinoAccountManagementPageViewModel : CoreBaseViewModel,
         => _ = LoadAsync();
 
     public void Receive(WinoAccountSignedOutMessage message)
-        => _ = ResetSignedOutStateAsync();
+        => _ = LoadAsync();
 
     private async Task LoadAsync()
     {
@@ -241,44 +245,25 @@ public partial class WinoAccountManagementPageViewModel : CoreBaseViewModel,
         try
         {
             var account = await _profileService.GetAuthenticatedAccountAsync().ConfigureAwait(false);
-
+            var addOns = await _addOnService.GetAvailableAddOnsAsync().ConfigureAwait(false);
-            if (account == null)
-            {
-                await ResetSignedOutStateAsync();
-                return;
-            }
-
-            var currentUserResponse = await _profileService.GetCurrentUserAsync().ConfigureAwait(false);
-            var aiStatusResponse = await _profileService.GetAiStatusAsync().ConfigureAwait(false);
-
-            var resolvedUser = currentUserResponse.IsSuccess && currentUserResponse.Result != null
-                ? currentUserResponse.Result
-                : new AuthUserDto(account.Id, account.Email, account.AccountStatus, account.HasPassword, account.HasGoogleLogin, account.HasFacebookLogin);
 
             await ExecuteUIThread(() =>
             {
-                IsSignedIn = true;
+                IsSignedIn = account != null;
-                AccountEmail = resolvedUser.Email;
+                AccountEmail = account?.Email ?? string.Empty;
-                AccountDisplayName = ExtractDisplayName(resolvedUser.Email);
+                AccountStatusText = account == null
-                AccountInitials = ExtractInitials(resolvedUser.Email);
+                    ? string.Empty
-                AccountStatusText = string.Format(Translator.WinoAccount_Management_StatusLabel, resolvedUser.AccountStatus);
+                    : string.Format(Translator.WinoAccount_Management_StatusLabel, account.AccountStatus);
             });
 
-            UpdateAiPackState(aiStatusResponse.IsSuccess ? aiStatusResponse.Result : null);
+            await UpdateAddOnsAsync(addOns).ConfigureAwait(false);
-
-            if (!currentUserResponse.IsSuccess || !aiStatusResponse.IsSuccess)
-            {
-                _dialogService.InfoBarMessage(Translator.GeneralTitle_Warning,
-                                              Translator.WinoAccount_Management_LoadFailed,
-                                              InfoBarMessageType.Warning);
-            }
         }
         catch (Exception)
         {
             _dialogService.InfoBarMessage(Translator.GeneralTitle_Error,
                                           Translator.WinoAccount_Management_LoadFailed,
                                           InfoBarMessageType.Error);
-            await ResetSignedOutStateAsync();
+            await ResetStateAsync().ConfigureAwait(false);
         }
         finally
         {
@@ -286,89 +271,54 @@ public partial class WinoAccountManagementPageViewModel : CoreBaseViewModel,
         }
     }
 
-    private async Task ResetSignedOutStateAsync()
+    private async Task ResetStateAsync()
     {
         await ExecuteUIThread(() =>
         {
             IsSignedIn = false;
-            AccountDisplayName = string.Empty;
-            AccountInitials = string.Empty;
             AccountEmail = string.Empty;
             AccountStatusText = string.Empty;
-            HasAiPack = false;
+            IsCheckoutInProgress = false;
-            AiPackStateText = Translator.WinoAccount_Management_AiPackInactive;
+            AddOns.Clear();
-            AiUsageSummary = string.Empty;
+            PurchaseAddOnCommand.NotifyCanExecuteChanged();
-            AiBillingPeriodSummary = string.Empty;
-            AiPackRenewalText = string.Empty;
-            AiUsageCount = 0;
-            AiUsageLimit = 1;
-            AiUsagePercentage = 0;
-            AiUsageResetText = string.Empty;
-            IsAiPackCheckoutInProgress = false;
         });
     }
 
-    private void UpdateAiPackState(AiStatusResultDto? aiStatus)
+    private async Task UpdateAddOnsAsync(IReadOnlyList<WinoAddOnInfo> addOns)
     {
-        var hasAiPack = aiStatus?.HasAiPack == true;
+        var items = addOns.Select(CreateAddOnItem).ToList();
-        var usageText = Translator.WinoAccount_Management_AiPackUnknownUsage;
-        var billingText = string.Empty;
-        var renewalText = string.Empty;
-        var usageCount = 0;
-        var usageLimit = 1;
-        var usagePercentage = 0d;
-        var resetText = string.Empty;
 
-        if (hasAiPack && aiStatus?.Used is int used && aiStatus.MonthlyLimit is int limit && aiStatus.Remaining is int remaining)
+        await ExecuteUIThread(() =>
         {
-            usageText = string.Format(Translator.WinoAccount_Management_AiPackUsage, used, limit, remaining);
+            AddOns.Clear();
-            usageCount = used;
-            usageLimit = limit > 0 ? limit : 1;
-            usagePercentage = (double)used / usageLimit * 100;
-        }
 
-        if (hasAiPack && aiStatus?.CurrentPeriodStartUtc is DateTimeOffset periodStart && aiStatus.CurrentPeriodEndUtc is DateTimeOffset periodEnd)
+            foreach (var item in items)
-        {
+            {
-            billingText = string.Format(Translator.WinoAccount_Management_AiPackBillingPeriod, periodStart.LocalDateTime, periodEnd.LocalDateTime);
+                AddOns.Add(item);
-            renewalText = string.Format(Translator.WinoAccount_Management_AiPackRenews, periodEnd.LocalDateTime);
+            }
-            resetText = string.Format(Translator.WinoAccount_Management_AiPackResets, periodEnd.LocalDateTime);
-        }
 
-        _ = ExecuteUIThread(() =>
+            PurchaseAddOnCommand.NotifyCanExecuteChanged();
-        {
-            HasAiPack = hasAiPack;
-            AiPackStateText = hasAiPack
-                ? Translator.WinoAccount_Management_AiPackActive
-                : Translator.WinoAccount_Management_AiPackInactive;
-            AiUsageSummary = hasAiPack ? usageText : string.Empty;
-            AiBillingPeriodSummary = hasAiPack ? billingText : string.Empty;
-            AiPackRenewalText = hasAiPack ? renewalText : string.Empty;
-            AiUsageCount = usageCount;
-            AiUsageLimit = usageLimit;
-            AiUsagePercentage = usagePercentage;
-            AiUsageResetText = hasAiPack ? resetText : string.Empty;
         });
     }
 
-    private static string ExtractDisplayName(string email)
+    private WinoAddOnItemViewModel CreateAddOnItem(WinoAddOnInfo addOn)
     {
-        if (string.IsNullOrWhiteSpace(email))
+        var item = new WinoAddOnItemViewModel(addOn.ProductType)
-            return string.Empty;
+        {
+            IsPurchased = addOn.IsPurchased,
+            PurchaseCommand = PurchaseAddOnCommand,
+            ManageCommand = ManageAiPackCommand,
+            UsageCount = addOn.UsageCount ?? 0,
+            UsageLimit = addOn.UsageLimit is > 0 ? addOn.UsageLimit.Value : 1,
+            UsagePercentage = addOn.UsagePercentage
+        };
 
-        var atIndex = email.IndexOf('@');
+        if (addOn.RenewalDateUtc is DateTimeOffset renewalDateUtc)
-        var localPart = atIndex > 0 ? email[..atIndex] : email;
+        {
+            item.RenewalText = string.Format(Translator.WinoAccount_Management_AiPackRenews, renewalDateUtc.LocalDateTime);
+            item.UsageResetText = string.Format(Translator.WinoAccount_Management_AiPackResets, renewalDateUtc.LocalDateTime);
+        }
 
-        if (localPart.Length == 0)
+        return item;
-            return string.Empty;
-
-        return char.ToUpper(localPart[0], CultureInfo.CurrentCulture) + localPart[1..];
-    }
-
-    private static string ExtractInitials(string email)
-    {
-        var displayName = ExtractDisplayName(email);
-        return displayName.Length > 0
-            ? displayName[..1].ToUpper(CultureInfo.CurrentCulture)
-            : string.Empty;
     }
 }

Wino.Mail.ViewModels/AccountManagementViewModel.cs

@@ -37,11 +37,12 @@ public partial class AccountManagementViewModel : AccountManagementPageViewModel
                                       IAccountService accountService,
                                       IProviderService providerService,
                                       IStoreManagementService storeManagementService,
+                                      IWinoAccountProfileService winoAccountProfileService,
                                       IWinoLogger winoLogger,
                                       ISpecialImapProviderConfigResolver specialImapProviderConfigResolver,
                                       ICalDavClient calDavClient,
                                       IAuthenticationProvider authenticationProvider,
-                                      IPreferencesService preferencesService) : base(dialogService, navigationService, accountService, providerService, storeManagementService, authenticationProvider, preferencesService)
+                                      IPreferencesService preferencesService) : base(dialogService, navigationService, accountService, providerService, storeManagementService, winoAccountProfileService, authenticationProvider, preferencesService)
     {
         MailDialogService = dialogService;
         _winoLogger = winoLogger;

Wino.Mail.WinUI/Dialogs/WinoAccountLoginDialog.xaml.cs

@@ -62,7 +62,7 @@ public sealed partial class WinoAccountLoginDialog : ContentDialog
 
             if (!result.IsSuccess || result.Account == null)
             {
-                ShowError(WinoAccountAuthErrorTranslator.Translate(result.ErrorCode));
+                ShowError(WinoAccountAuthErrorTranslator.Format(result.ErrorCode, result.ErrorMessage));
                 return;
             }
 

Wino.Mail.WinUI/Dialogs/WinoAccountRegistrationDialog.xaml.cs

@@ -64,7 +64,7 @@ public sealed partial class WinoAccountRegistrationDialog : ContentDialog
 
             if (!result.IsSuccess || result.Account == null)
             {
-                ShowError(WinoAccountAuthErrorTranslator.Translate(result.ErrorCode));
+                ShowError(WinoAccountAuthErrorTranslator.Format(result.ErrorCode, result.ErrorMessage));
                 return;
             }
 

Wino.Mail.WinUI/Selectors/WinoAddOnTemplateSelector.cs

@@ -0,0 +1,30 @@
+using System;
+using Microsoft.UI.Xaml;
+using Microsoft.UI.Xaml.Controls;
+using Wino.Core.Domain.Enums;
+using Wino.Core.ViewModels.Data;
+
+namespace Wino.Selectors;
+
+public partial class WinoAddOnTemplateSelector : DataTemplateSelector
+{
+    public DataTemplate? NotPurchasedTemplate { get; set; }
+    public DataTemplate? AiPackPurchasedTemplate { get; set; }
+    public DataTemplate? UnlimitedAccountsPurchasedTemplate { get; set; }
+
+    protected override DataTemplate SelectTemplateCore(object item, DependencyObject container)
+    {
+        if (item is not WinoAddOnItemViewModel addOn)
+            throw new ArgumentException(nameof(item));
+
+        if (!addOn.IsPurchased)
+            return NotPurchasedTemplate ?? throw new ArgumentException(nameof(NotPurchasedTemplate));
+
+        return addOn.ProductType switch
+        {
+            WinoAddOnProductType.AI_PACK => AiPackPurchasedTemplate ?? throw new ArgumentException(nameof(AiPackPurchasedTemplate)),
+            WinoAddOnProductType.UNLIMITED_ACCOUNTS => UnlimitedAccountsPurchasedTemplate ?? throw new ArgumentException(nameof(UnlimitedAccountsPurchasedTemplate)),
+            _ => NotPurchasedTemplate ?? throw new ArgumentException(nameof(NotPurchasedTemplate))
+        };
+    }
+}

Wino.Mail.WinUI/Services/StoreManagementService.cs

@@ -3,8 +3,8 @@ using System.Collections.Generic;
 using System.Threading.Tasks;
 using Windows.Services.Store;
 using Wino.Core.Domain.Interfaces;
-using Wino.Core.Domain.Models.Store;
 using WinoStorePurchaseResult = Wino.Core.Domain.Enums.StorePurchaseResult;
+using WinoAddOnProductType = Wino.Core.Domain.Enums.WinoAddOnProductType;
 
 namespace Wino.Mail.WinUI.Services;
 
@@ -12,14 +12,14 @@ public class StoreManagementService : IStoreManagementService
 {
     private StoreContext CurrentContext { get; }
 
-    private readonly Dictionary<StoreProductType, string> productIds = new Dictionary<StoreProductType, string>()
+    private readonly Dictionary<WinoAddOnProductType, string> productIds = new Dictionary<WinoAddOnProductType, string>()
     {
-        { StoreProductType.UnlimitedAccounts, "UnlimitedAccounts" }
+        { WinoAddOnProductType.UNLIMITED_ACCOUNTS, "UnlimitedAccounts" }
     };
 
-    private readonly Dictionary<StoreProductType, string> skuIds = new Dictionary<StoreProductType, string>()
+    private readonly Dictionary<WinoAddOnProductType, string> skuIds = new Dictionary<WinoAddOnProductType, string>()
     {
-        { StoreProductType.UnlimitedAccounts, "9P02MXZ42GSM" }
+        { WinoAddOnProductType.UNLIMITED_ACCOUNTS, "9P02MXZ42GSM" }
     };
 
     public StoreManagementService()
@@ -27,9 +27,11 @@ public class StoreManagementService : IStoreManagementService
         CurrentContext = StoreContext.GetDefault();
     }
 
-    public async Task<bool> HasProductAsync(StoreProductType productType)
+    public async Task<bool> HasProductAsync(WinoAddOnProductType productType)
     {
-        var productKey = productIds[productType];
+        if (!productIds.TryGetValue(productType, out var productKey))
+            return false;
+
         var appLicense = await CurrentContext.GetAppLicenseAsync();
 
         if (appLicense == null)
@@ -49,14 +51,15 @@ public class StoreManagementService : IStoreManagementService
         return false;
     }
 
-    public async Task<WinoStorePurchaseResult> PurchaseAsync(StoreProductType productType)
+    public async Task<WinoStorePurchaseResult> PurchaseAsync(WinoAddOnProductType productType)
     {
+        if (!skuIds.TryGetValue(productType, out var productKey))
+            return WinoStorePurchaseResult.NotPurchased;
+
         if (await HasProductAsync(productType))
             return WinoStorePurchaseResult.AlreadyPurchased;
         else
         {
-            var productKey = skuIds[productType];
-
             var result = await CurrentContext.RequestPurchaseAsync(productKey);
 
             switch (result.Status)

Wino.Mail.WinUI/Services/WinoAccountAuthErrorTranslator.cs

@@ -30,4 +30,34 @@ public static class WinoAccountAuthErrorTranslator
             _ => errorCode
         };
     }
+
+    public static string Format(string? errorCode, string? errorMessage)
+    {
+        var translatedCode = Translate(errorCode);
+        var hasCode = !string.IsNullOrWhiteSpace(errorCode);
+        var hasMessage = !string.IsNullOrWhiteSpace(errorMessage);
+
+        if (!hasCode && !hasMessage)
+        {
+            return Translator.GeneralTitle_Error;
+        }
+
+        var formattedCode = translatedCode;
+        if (hasCode && !string.Equals(translatedCode, errorCode, System.StringComparison.Ordinal))
+        {
+            formattedCode = $"{translatedCode} ({errorCode})";
+        }
+
+        if (!hasMessage || string.Equals(errorMessage, translatedCode, System.StringComparison.OrdinalIgnoreCase) || string.Equals(errorMessage, errorCode, System.StringComparison.OrdinalIgnoreCase))
+        {
+            return formattedCode;
+        }
+
+        if (string.IsNullOrWhiteSpace(formattedCode))
+        {
+            return errorMessage!;
+        }
+
+        return $"{formattedCode}{System.Environment.NewLine}{errorMessage}";
+    }
 }

Wino.Mail.WinUI/Views/Settings/WinoAccountManagementPage.xaml

@@ -7,13 +7,172 @@
     xmlns:d="http://schemas.microsoft.com/expression/blend/2008"
     xmlns:domain="using:Wino.Core.Domain"
     xmlns:mc="http://schemas.openxmlformats.org/markup-compatibility/2006"
+    xmlns:selectors="using:Wino.Selectors"
+    xmlns:viewModelData="using:Wino.Core.ViewModels.Data"
+    x:Name="root"
     Title="{x:Bind domain:Translator.WinoAccount_SettingsSection_Title}"
     mc:Ignorable="d">
 
+    <Page.Resources>
+        <DataTemplate x:Key="AddOnNotPurchasedTemplate" x:DataType="viewModelData:WinoAddOnItemViewModel">
+            <controls:SettingsCard ActionIcon="Add" IsActionIconVisible="True">
+                <controls:SettingsCard.HeaderIcon>
+                    <FontIcon FontFamily="{StaticResource SymbolThemeFontFamily}" Glyph="{x:Bind IconGlyph}" />
+                </controls:SettingsCard.HeaderIcon>
+                <controls:SettingsCard.Header>
+                    <StackPanel Spacing="8">
+                        <TextBlock FontWeight="SemiBold" Text="{x:Bind domain:Translator.GetTranslatedString(NameKey), Mode=OneWay}" />
+                        <TextBlock
+                            Foreground="{ThemeResource TextFillColorSecondaryBrush}"
+                            Style="{StaticResource BodyTextBlockStyle}"
+                            Text="{x:Bind domain:Translator.GetTranslatedString(DescriptionKey), Mode=OneWay}"
+                            TextWrapping="WrapWholeWords" />
+                        <TextBlock
+                            Foreground="{ThemeResource TextFillColorSecondaryBrush}"
+                            Style="{StaticResource CaptionTextBlockStyle}"
+                            Text="{x:Bind domain:Translator.GetTranslatedString(KeywordsKey), Mode=OneWay}"
+                            TextWrapping="WrapWholeWords" />
+                        <StackPanel
+                            Margin="0,4,0,0"
+                            Orientation="Horizontal"
+                            Spacing="12">
+                            <Button
+                                Command="{x:Bind PurchaseCommand, Mode=OneWay}"
+                                CommandParameter="{x:Bind}"
+                                Content="{x:Bind domain:Translator.Buttons_Purchase}"
+                                Style="{StaticResource AccentButtonStyle}" />
+                            <ProgressRing
+                                Width="18"
+                                Height="18"
+                                IsActive="{x:Bind IsPurchaseInProgress, Mode=OneWay}"
+                                Visibility="{x:Bind IsPurchaseInProgress, Mode=OneWay}" />
+                        </StackPanel>
+                    </StackPanel>
+                </controls:SettingsCard.Header>
+            </controls:SettingsCard>
+        </DataTemplate>
+
+        <DataTemplate x:Key="AiPackPurchasedTemplate" x:DataType="viewModelData:WinoAddOnItemViewModel">
+            <controls:SettingsExpander IsExpanded="True">
+                <controls:SettingsExpander.HeaderIcon>
+                    <FontIcon FontFamily="{StaticResource SymbolThemeFontFamily}" Glyph="{x:Bind IconGlyph}" />
+                </controls:SettingsExpander.HeaderIcon>
+                <controls:SettingsExpander.Header>
+                    <StackPanel Orientation="Horizontal" Spacing="8">
+                        <TextBlock FontWeight="SemiBold" Text="{x:Bind domain:Translator.GetTranslatedString(NameKey), Mode=OneWay}" />
+                        <Border
+                            Padding="8,2"
+                            Background="{ThemeResource SystemAccentColor}"
+                            CornerRadius="4">
+                            <TextBlock
+                                FontSize="10"
+                                FontWeight="Bold"
+                                Foreground="White"
+                                Text="PRO" />
+                        </Border>
+                    </StackPanel>
+                </controls:SettingsExpander.Header>
+                <controls:SettingsExpander.Description>
+                    <StackPanel Orientation="Horizontal" Spacing="4">
+                        <TextBlock
+                            Foreground="{ThemeResource TextFillColorSecondaryBrush}"
+                            Style="{StaticResource CaptionTextBlockStyle}"
+                            Text="{x:Bind domain:Translator.WinoAccount_Management_AiPackSubscriptionActive}" />
+                        <TextBlock
+                            Foreground="{ThemeResource TextFillColorSecondaryBrush}"
+                            Style="{StaticResource CaptionTextBlockStyle}"
+                            Text=" · " />
+                        <TextBlock
+                            Foreground="{ThemeResource TextFillColorSecondaryBrush}"
+                            Style="{StaticResource CaptionTextBlockStyle}"
+                            Text="{x:Bind RenewalText, Mode=OneWay}" />
+                    </StackPanel>
+                </controls:SettingsExpander.Description>
+                <HyperlinkButton Command="{x:Bind ManageCommand, Mode=OneWay}" Content="{x:Bind domain:Translator.Buttons_Manage}" />
+                <controls:SettingsExpander.Items>
+                    <controls:SettingsCard HorizontalContentAlignment="Stretch">
+                        <controls:SettingsCard.Header>
+                            <StackPanel MinWidth="400" Spacing="8">
+                                <StackPanel Orientation="Horizontal" Spacing="4">
+                                    <TextBlock
+                                        FontSize="24"
+                                        FontWeight="Bold"
+                                        Text="{x:Bind UsageCount, Mode=OneWay}" />
+                                    <TextBlock
+                                        Margin="0,0,0,2"
+                                        VerticalAlignment="Bottom"
+                                        Foreground="{ThemeResource TextFillColorSecondaryBrush}"
+                                        Style="{StaticResource CaptionTextBlockStyle}">
+                                        <Run Text="/ " />
+                                        <Run Text="{x:Bind UsageLimit, Mode=OneWay}" />
+                                    </TextBlock>
+                                </StackPanel>
+                                <ProgressBar
+                                    Height="8"
+                                    Maximum="100"
+                                    Value="{x:Bind UsagePercentage, Mode=OneWay}" />
+                                <Grid>
+                                    <TextBlock
+                                        HorizontalAlignment="Left"
+                                        Foreground="{ThemeResource TextFillColorSecondaryBrush}"
+                                        Style="{StaticResource CaptionTextBlockStyle}"
+                                        Text="{x:Bind domain:Translator.WinoAccount_Management_AiPackRequestsUsed}" />
+                                    <TextBlock
+                                        HorizontalAlignment="Right"
+                                        Foreground="{ThemeResource TextFillColorSecondaryBrush}"
+                                        Style="{StaticResource CaptionTextBlockStyle}"
+                                        Text="{x:Bind UsageResetText, Mode=OneWay}" />
+                                </Grid>
+                            </StackPanel>
+                        </controls:SettingsCard.Header>
+                    </controls:SettingsCard>
+                </controls:SettingsExpander.Items>
+            </controls:SettingsExpander>
+        </DataTemplate>
+
+        <DataTemplate x:Key="UnlimitedAccountsPurchasedTemplate" x:DataType="viewModelData:WinoAddOnItemViewModel">
+            <controls:SettingsCard>
+                <controls:SettingsCard.HeaderIcon>
+                    <FontIcon FontFamily="{StaticResource SymbolThemeFontFamily}" Glyph="{x:Bind IconGlyph}" />
+                </controls:SettingsCard.HeaderIcon>
+                <controls:SettingsCard.Header>
+                    <StackPanel Spacing="8">
+                        <TextBlock FontWeight="SemiBold" Text="{x:Bind domain:Translator.GetTranslatedString(NameKey), Mode=OneWay}" />
+                        <TextBlock
+                            Foreground="{ThemeResource TextFillColorSecondaryBrush}"
+                            Style="{StaticResource BodyTextBlockStyle}"
+                            Text="{x:Bind domain:Translator.GetTranslatedString(DescriptionKey), Mode=OneWay}"
+                            TextWrapping="WrapWholeWords" />
+                        <TextBlock
+                            Foreground="{ThemeResource TextFillColorSecondaryBrush}"
+                            Style="{StaticResource CaptionTextBlockStyle}"
+                            Text="{x:Bind domain:Translator.GetTranslatedString(KeywordsKey), Mode=OneWay}"
+                            TextWrapping="WrapWholeWords" />
+                        <Border
+                            Padding="12,4"
+                            HorizontalAlignment="Left"
+                            Background="{ThemeResource SystemFillColorSuccessBackgroundBrush}"
+                            CornerRadius="12">
+                            <TextBlock
+                                Foreground="{ThemeResource SystemFillColorSuccessBrush}"
+                                Style="{StaticResource CaptionTextBlockStyle}"
+                                Text="{x:Bind domain:Translator.Purchased}" />
+                        </Border>
+                    </StackPanel>
+                </controls:SettingsCard.Header>
+            </controls:SettingsCard>
+        </DataTemplate>
+
+        <selectors:WinoAddOnTemplateSelector
+            x:Key="WinoAddOnTemplateSelector"
+            AiPackPurchasedTemplate="{StaticResource AiPackPurchasedTemplate}"
+            NotPurchasedTemplate="{StaticResource AddOnNotPurchasedTemplate}"
+            UnlimitedAccountsPurchasedTemplate="{StaticResource UnlimitedAccountsPurchasedTemplate}" />
+    </Page.Resources>
+
     <ScrollViewer>
         <StackPanel Spacing="{StaticResource SettingsCardSpacing}">
 
-            <!--  Busy indicator  -->
             <StackPanel
                 x:Name="BusyPanel"
                 HorizontalAlignment="Center"
@@ -26,34 +185,29 @@
                 <TextBlock HorizontalAlignment="Center" Text="{x:Bind domain:Translator.Busy}" />
             </StackPanel>
 
-            <!--  ══════════════════════════════════════  -->
-            <!--  SIGNED-OUT VIEW  -->
-            <!--  ══════════════════════════════════════  -->
             <StackPanel
                 x:Name="SignedOutPanel"
+                HorizontalAlignment="Stretch"
                 x:Load="{x:Bind ViewModel.IsSignedOut, Mode=OneWay}"
                 Spacing="{StaticResource SettingsCardSpacing}">
 
                 <StackPanel
                     Padding="0,40,0,40"
-                    HorizontalAlignment="Center"
+                    HorizontalAlignment="Stretch"
                     Spacing="16">
 
-                    <!--  App logo  -->
                     <Image
                         Width="64"
                         Height="64"
                         HorizontalAlignment="Center"
                         Source="ms-appx:///Assets/AppEntries/MailAssets/Square150x150Logo.scale-100.png" />
 
-                    <!--  Title  -->
                     <TextBlock
                         HorizontalAlignment="Center"
                         FontSize="20"
                         FontWeight="SemiBold"
                         Text="{x:Bind domain:Translator.WinoAccount_Management_SignedOutTitle}" />
 
-                    <!--  Description  -->
                     <TextBlock
                         MaxWidth="360"
                         HorizontalAlignment="Center"
@@ -63,7 +217,6 @@
                         TextAlignment="Center"
                         TextWrapping="WrapWholeWords" />
 
-                    <!--  Action buttons  -->
                     <StackPanel
                         HorizontalAlignment="Center"
                         Orientation="Horizontal"
@@ -79,127 +232,34 @@
                         Margin="0,16,0,4"
                         HorizontalAlignment="Center"
                         Style="{StaticResource BodyStrongTextBlockStyle}"
-                        Text="{x:Bind domain:Translator.WinoAccount_Management_AiPackSectionHeader}" />
+                        Text="{x:Bind domain:Translator.WinoAccount_Management_AddOnsSectionHeader}" />
 
-                    <controls:SettingsCard
+                    <ListView
-                        MaxWidth="520"
+                        x:Name="SignedOutAddOnsList"
-                        Description="{x:Bind domain:Translator.WinoAccount_Management_AiPackPromoDescription}">
+                        ItemContainerStyle="{StaticResource StretchedItemContainerStyle}"
-                        <controls:SettingsCard.HeaderIcon>
+                        ItemTemplateSelector="{StaticResource WinoAddOnTemplateSelector}"
-                            <FontIcon FontFamily="{StaticResource SymbolThemeFontFamily}" Glyph="&#xE945;" />
+                        ItemsSource="{x:Bind ViewModel.AddOns, Mode=OneWay}"
-                        </controls:SettingsCard.HeaderIcon>
+                        SelectionMode="None" />
-                        <controls:SettingsCard.Header>
-                            <StackPanel Spacing="8">
-                                <StackPanel Orientation="Horizontal" Spacing="8">
-                                    <TextBlock FontWeight="SemiBold" Text="{x:Bind domain:Translator.WinoAccount_Management_AiPackPromoTitle}" />
-                                    <Border
-                                        Padding="8,2"
-                                        Background="{ThemeResource SystemAccentColor}"
-                                        CornerRadius="4">
-                                        <TextBlock
-                                            FontSize="10"
-                                            FontWeight="Bold"
-                                            Foreground="White"
-                                            Text="PRO" />
-                                    </Border>
-                                </StackPanel>
-                                <TextBlock
-                                    MaxWidth="400"
-                                    Foreground="{ThemeResource TextFillColorSecondaryBrush}"
-                                    Style="{StaticResource CaptionTextBlockStyle}"
-                                    Text="{x:Bind domain:Translator.WinoAccount_Management_AiPackPromoDescription}"
-                                    TextWrapping="WrapWholeWords" />
-                                <StackPanel Orientation="Horizontal" Spacing="16">
-                                    <StackPanel Orientation="Horizontal" Spacing="4">
-                                        <FontIcon
-                                            FontFamily="{StaticResource SymbolThemeFontFamily}"
-                                            FontSize="12"
-                                            Glyph="&#xE8C1;" />
-                                        <TextBlock Style="{StaticResource CaptionTextBlockStyle}" Text="{x:Bind domain:Translator.WinoAccount_Management_AiPackFeatureTranslate}" />
-                                    </StackPanel>
-                                    <StackPanel Orientation="Horizontal" Spacing="4">
-                                        <FontIcon
-                                            FontFamily="{StaticResource SymbolThemeFontFamily}"
-                                            FontSize="12"
-                                            Glyph="&#xE70F;" />
-                                        <TextBlock Style="{StaticResource CaptionTextBlockStyle}" Text="{x:Bind domain:Translator.WinoAccount_Management_AiPackFeatureRewrite}" />
-                                    </StackPanel>
-                                    <StackPanel Orientation="Horizontal" Spacing="4">
-                                        <FontIcon
-                                            FontFamily="{StaticResource SymbolThemeFontFamily}"
-                                            FontSize="12"
-                                            Glyph="&#xE8FD;" />
-                                        <TextBlock Style="{StaticResource CaptionTextBlockStyle}" Text="{x:Bind domain:Translator.WinoAccount_Management_AiPackFeatureSummarize}" />
-                                    </StackPanel>
-                                </StackPanel>
-                                <Border
-                                    Padding="12,8"
-                                    Background="{ThemeResource SystemFillColorCautionBackgroundBrush}"
-                                    CornerRadius="8">
-                                    <TextBlock
-                                        Foreground="{ThemeResource SystemFillColorCautionBrush}"
-                                        Style="{StaticResource CaptionTextBlockStyle}"
-                                        Text="{x:Bind domain:Translator.WinoAccount_Management_PurchaseRequiresSignIn}"
-                                        TextWrapping="WrapWholeWords" />
-                                </Border>
-                                <StackPanel
-                                    Margin="0,4,0,0"
-                                    Orientation="Horizontal"
-                                    Spacing="12">
-                                    <Button
-                                        Command="{x:Bind ViewModel.BuyAiPackCommand}"
-                                        Content="{x:Bind domain:Translator.Buttons_Purchase}"
-                                        IsEnabled="{x:Bind ViewModel.CanBuyAiPack, Mode=OneWay}"
-                                        Style="{StaticResource AccentButtonStyle}" />
-                                    <ProgressRing
-                                        Width="18"
-                                        Height="18"
-                                        IsActive="True"
-                                        Visibility="{x:Bind ViewModel.IsAiPackCheckoutInProgress, Mode=OneWay}" />
-                                    <TextBlock
-                                        VerticalAlignment="Center"
-                                        Foreground="{ThemeResource TextFillColorSecondaryBrush}"
-                                        Style="{StaticResource CaptionTextBlockStyle}">
-                                        <Run Text="{x:Bind domain:Translator.WinoAccount_Management_AiPackPromoPrice}" />
-                                        <Run Text=" · " />
-                                        <Run Text="{x:Bind domain:Translator.WinoAccount_Management_AiPackPromoRequests}" />
-                                    </TextBlock>
-                                </StackPanel>
-                            </StackPanel>
-                        </controls:SettingsCard.Header>
-                    </controls:SettingsCard>
                 </StackPanel>
             </StackPanel>
 
-            <!--  ══════════════════════════════════════  -->
-            <!--  SIGNED-IN VIEW  -->
-            <!--  ══════════════════════════════════════  -->
             <StackPanel
                 x:Name="SignedInPanel"
                 x:Load="{x:Bind ViewModel.IsSignedIn, Mode=OneWay}"
                 Spacing="{StaticResource SettingsCardSpacing}">
 
-                <!--  ─── Profile section ───  -->
                 <TextBlock
                     Margin="0,0,0,4"
                     Style="{StaticResource BodyStrongTextBlockStyle}"
                     Text="{x:Bind domain:Translator.WinoAccount_Management_ProfileSectionHeader}" />
 
-                <controls:SettingsCard>
+                <controls:SettingsCard Header="{x:Bind ViewModel.AccountEmail, Mode=OneWay}">
-                    <controls:SettingsCard.Header>
+                    <controls:SettingsCard.HeaderIcon>
-                        <StackPanel Orientation="Horizontal" Spacing="12">
+                        <PathIcon
-                            <PersonPicture
+                            HorizontalAlignment="Center"
-                                Width="40"
+                            VerticalAlignment="Center"
-                                Height="40"
+                            Data="F1 M 3.75 5 L 3.75 4.902344 C 3.75 4.225262 3.885091 3.588867 4.155273 2.993164 C 4.425456 2.397461 4.790039 1.878256 5.249023 1.435547 C 5.708008 0.99284 6.238606 0.642904 6.84082 0.385742 C 7.443034 0.128582 8.079427 0 8.75 0 C 9.440104 0 10.089518 0.130209 10.698242 0.390625 C 11.306966 0.651043 11.837564 1.007488 12.290039 1.459961 C 12.742513 1.912436 13.098958 2.443035 13.359375 3.051758 C 13.619791 3.660482 13.75 4.309896 13.75 5 C 13.75 5.690104 13.619791 6.339519 13.359375 6.948242 C 13.098958 7.556967 12.742513 8.087565 12.290039 8.540039 C 11.837564 8.992514 11.306966 9.348959 10.698242 9.609375 C 10.089518 9.869792 9.440104 10 8.75 10 C 8.059896 10 7.410481 9.869792 6.801758 9.609375 C 6.193034 9.348959 5.662435 8.992514 5.209961 8.540039 C 4.757487 8.087565 4.401042 7.556967 4.140625 6.948242 C 3.880208 6.339519 3.75 5.690104 3.75 5 Z M 5 5 L 5 5.078125 C 5 5.585938 5.100911 6.062826 5.302734 6.508789 C 5.504557 6.954753 5.777995 7.34375 6.123047 7.675781 C 6.468099 8.007812 6.866862 8.269857 7.319336 8.461914 C 7.77181 8.653972 8.248697 8.75 8.75 8.75 C 9.270833 8.75 9.759114 8.652344 10.214844 8.457031 C 10.670572 8.261719 11.067708 7.994792 11.40625 7.65625 C 11.744791 7.317709 12.011719 6.920573 12.207031 6.464844 C 12.402344 6.009115 12.5 5.520834 12.5 5 C 12.5 4.479167 12.402344 3.990887 12.207031 3.535156 C 12.011719 3.079428 11.744791 2.682293 11.40625 2.34375 C 11.067708 2.005209 10.670572 1.738281 10.214844 1.542969 C 9.759114 1.347656 9.270833 1.25 8.75 1.25 C 8.229166 1.25 7.740885 1.347656 7.285156 1.542969 C 6.829427 1.738281 6.432292 2.005209 6.09375 2.34375 C 5.755208 2.682293 5.488281 3.079428 5.292969 3.535156 C 5.097656 3.990887 5 4.479167 5 5 Z M 20 14.375 L 20 18.125 C 20 18.385416 19.951172 18.629557 19.853516 18.857422 C 19.755859 19.085287 19.622395 19.283854 19.453125 19.453125 C 19.283854 19.622396 19.085285 19.755859 18.857422 19.853516 C 18.629557 19.951172 18.385416 20 18.125 20 L 11.875 20 C 11.614583 20 11.370442 19.951172 11.142578 19.853516 C 10.914713 19.755859 10.716146 19.622396 10.546875 19.453125 C 10.377604 19.283854 10.244141 19.085287 10.146484 18.857422 C 10.048828 18.629557 10 18.385416 10 18.125 L 10 14.375 C 10 14.114584 10.048828 13.870443 10.146484 13.642578 C 10.244141 13.414714 10.377604 13.216146 10.546875 13.046875 C 10.716146 12.877604 10.914713 12.744141 11.142578 12.646484 C 11.370442 12.548828 11.614583 12.5 11.875 12.5 L 12.5 12.5 L 12.5 11.25 C 12.5 11.080729 12.532552 10.921225 12.597656 10.771484 C 12.66276 10.621745 12.753906 10.488281 12.871094 10.371094 C 13.118488 10.123698 13.411457 10 13.75 10 L 16.25 10 C 16.41927 10 16.578775 10.032553 16.728516 10.097656 C 16.878254 10.162761 17.011719 10.253906 17.128906 10.371094 C 17.376301 10.61849 17.5 10.911459 17.5 11.25 L 17.5 12.5 L 18.125 12.5 C 18.385416 12.5 18.629557 12.548828 18.857422 12.646484 C 19.085285 12.744141 19.283854 12.877604 19.453125 13.046875 C 19.622395 13.216146 19.755859 13.414714 19.853516 13.642578 C 19.951172 13.870443 20 14.114584 20 14.375 Z M 11.25 11.25 C 10.800781 11.25 10.382486 11.360678 9.995117 11.582031 C 9.607747 11.803386 9.303385 12.109375 9.082031 12.5 L 2.5 12.5 C 2.324219 12.5 2.159831 12.532553 2.006836 12.597656 C 1.853841 12.662761 1.722005 12.750651 1.611328 12.861328 C 1.500651 12.972006 1.41276 13.103842 1.347656 13.256836 C 1.282552 13.409831 1.25 13.574219 1.25 13.75 C 1.25 14.420573 1.360677 15.008139 1.582031 15.512695 C 1.803385 16.017252 2.102865 16.455078 2.480469 16.826172 C 2.858073 17.197266 3.297526 17.50651 3.798828 17.753906 C 4.30013 18.001303 4.827474 18.198242 5.380859 18.344727 C 5.934244 18.491211 6.50065 18.595377 7.080078 18.657227 C 7.659505 18.719076 8.216146 18.75 8.75 18.75 C 8.75 19.205729 8.860677 19.622396 9.082031 20 L 8.75 20 C 8.190104 20 7.618814 19.973959 7.036133 19.921875 C 6.45345 19.869791 5.878906 19.775391 5.3125 19.638672 C 4.746094 19.501953 4.197591 19.319662 3.666992 19.091797 C 3.136393 18.863932 2.646484 18.574219 2.197266 18.222656 C 1.474609 17.66276 0.927734 17.005209 0.556641 16.25 C 0.185547 15.494792 0 14.661458 0 13.75 C 0 13.404948 0.065104 13.081055 0.195312 12.77832 C 0.325521 12.475586 0.504557 12.210287 0.732422 11.982422 C 0.960286 11.754558 1.225586 11.575521 1.52832 11.445312 C 1.831055 11.315104 2.154948 11.25 2.5 11.25 Z M 16.25 11.25 L 13.75 11.25 L 13.75 12.5 L 16.25 12.5 Z " />
-                                Initials="{x:Bind ViewModel.AccountInitials, Mode=OneWay}" />
+                    </controls:SettingsCard.HeaderIcon>
-                            <StackPanel VerticalAlignment="Center" Spacing="2">
-                                <TextBlock FontWeight="SemiBold" Text="{x:Bind ViewModel.AccountDisplayName, Mode=OneWay}" />
-                                <TextBlock
-                                    Foreground="{ThemeResource TextFillColorSecondaryBrush}"
-                                    Style="{StaticResource CaptionTextBlockStyle}"
-                                    Text="{x:Bind ViewModel.AccountEmail, Mode=OneWay}" />
-                            </StackPanel>
-                        </StackPanel>
-                    </controls:SettingsCard.Header>
                     <Border
                         Padding="12,4"
                         Background="{ThemeResource SystemFillColorSuccessBackgroundBrush}"
@@ -211,197 +271,36 @@
                     </Border>
                 </controls:SettingsCard>
 
-                <!--  ─── AI Pack section ───  -->
                 <TextBlock
                     Margin="0,12,0,4"
                     Style="{StaticResource BodyStrongTextBlockStyle}"
-                    Text="{x:Bind domain:Translator.WinoAccount_Management_AiPackSectionHeader}" />
+                    Text="{x:Bind domain:Translator.WinoAccount_Management_AddOnsSectionHeader}" />
 
-                <!--  AI Pack promo (no AI Pack)  -->
+                <ListView
-                <controls:SettingsCard
+                    x:Name="SignedInAddOnsList"
-                    x:Name="AiPackPromoCard"
+                    ItemContainerStyle="{StaticResource StretchedItemContainerStyle}"
-                    x:Load="{x:Bind ViewModel.CanShowBuyAiPack, Mode=OneWay}"
+                    ItemTemplateSelector="{StaticResource WinoAddOnTemplateSelector}"
-                    Description="{x:Bind domain:Translator.WinoAccount_Management_AiPackPromoDescription}">
+                    ItemsSource="{x:Bind ViewModel.AddOns, Mode=OneWay}"
-                    <controls:SettingsCard.HeaderIcon>
+                    SelectionMode="None" />
-                        <FontIcon FontFamily="{StaticResource SymbolThemeFontFamily}" Glyph="&#xE945;" />
-                    </controls:SettingsCard.HeaderIcon>
-                    <controls:SettingsCard.Header>
-                        <StackPanel Spacing="8">
-                            <StackPanel Orientation="Horizontal" Spacing="8">
-                                <TextBlock FontWeight="SemiBold" Text="{x:Bind domain:Translator.WinoAccount_Management_AiPackPromoTitle}" />
-                                <Border
-                                    Padding="8,2"
-                                    Background="{ThemeResource SystemAccentColor}"
-                                    CornerRadius="4">
-                                    <TextBlock
-                                        FontSize="10"
-                                        FontWeight="Bold"
-                                        Foreground="White"
-                                        Text="PRO" />
-                                </Border>
-                            </StackPanel>
-                            <TextBlock
-                                MaxWidth="400"
-                                Foreground="{ThemeResource TextFillColorSecondaryBrush}"
-                                Style="{StaticResource CaptionTextBlockStyle}"
-                                Text="{x:Bind domain:Translator.WinoAccount_Management_AiPackPromoDescription}"
-                                TextWrapping="WrapWholeWords" />
-                            <StackPanel Orientation="Horizontal" Spacing="16">
-                                <StackPanel Orientation="Horizontal" Spacing="4">
-                                    <FontIcon
-                                        FontFamily="{StaticResource SymbolThemeFontFamily}"
-                                        FontSize="12"
-                                        Glyph="&#xE8C1;" />
-                                    <TextBlock Style="{StaticResource CaptionTextBlockStyle}" Text="{x:Bind domain:Translator.WinoAccount_Management_AiPackFeatureTranslate}" />
-                                </StackPanel>
-                                <StackPanel Orientation="Horizontal" Spacing="4">
-                                    <FontIcon
-                                        FontFamily="{StaticResource SymbolThemeFontFamily}"
-                                        FontSize="12"
-                                        Glyph="&#xE70F;" />
-                                    <TextBlock Style="{StaticResource CaptionTextBlockStyle}" Text="{x:Bind domain:Translator.WinoAccount_Management_AiPackFeatureRewrite}" />
-                                </StackPanel>
-                                <StackPanel Orientation="Horizontal" Spacing="4">
-                                    <FontIcon
-                                        FontFamily="{StaticResource SymbolThemeFontFamily}"
-                                        FontSize="12"
-                                        Glyph="&#xE8FD;" />
-                                    <TextBlock Style="{StaticResource CaptionTextBlockStyle}" Text="{x:Bind domain:Translator.WinoAccount_Management_AiPackFeatureSummarize}" />
-                                </StackPanel>
-                            </StackPanel>
-                            <StackPanel
-                                Margin="0,4,0,0"
-                                Orientation="Horizontal"
-                                Spacing="12">
-                                <Button
-                                    Command="{x:Bind ViewModel.BuyAiPackCommand}"
-                                    Content="{x:Bind domain:Translator.Buttons_Purchase}"
-                                    IsEnabled="{x:Bind ViewModel.CanBuyAiPack, Mode=OneWay}"
-                                    Style="{StaticResource AccentButtonStyle}" />
-                                <ProgressRing
-                                    Width="18"
-                                    Height="18"
-                                    IsActive="True"
-                                    Visibility="{x:Bind ViewModel.IsAiPackCheckoutInProgress, Mode=OneWay}" />
-                                <TextBlock
-                                    VerticalAlignment="Center"
-                                    Foreground="{ThemeResource TextFillColorSecondaryBrush}"
-                                    Style="{StaticResource CaptionTextBlockStyle}">
-                                    <Run Text="{x:Bind domain:Translator.WinoAccount_Management_AiPackPromoPrice}" />
-                                    <Run Text=" · " />
-                                    <Run Text="{x:Bind domain:Translator.WinoAccount_Management_AiPackPromoRequests}" />
-                                </TextBlock>
-                            </StackPanel>
-                        </StackPanel>
-                    </controls:SettingsCard.Header>
-                </controls:SettingsCard>
 
-                <!--  AI Pack active: subscription info  -->
-                <controls:SettingsExpander
-                    x:Name="AiPackActiveCard"
-                    x:Load="{x:Bind ViewModel.HasAiPack, Mode=OneWay}"
-                    IsExpanded="True">
-                    <controls:SettingsExpander.HeaderIcon>
-                        <FontIcon FontFamily="{StaticResource SymbolThemeFontFamily}" Glyph="&#xE945;" />
-                    </controls:SettingsExpander.HeaderIcon>
-                    <controls:SettingsExpander.Header>
-                        <StackPanel Orientation="Horizontal" Spacing="8">
-                            <TextBlock FontWeight="SemiBold" Text="{x:Bind domain:Translator.WinoAccount_Management_AiPackCardTitle}" />
-                            <Border
-                                Padding="8,2"
-                                Background="{ThemeResource SystemAccentColor}"
-                                CornerRadius="4">
-                                <TextBlock
-                                    FontSize="10"
-                                    FontWeight="Bold"
-                                    Foreground="White"
-                                    Text="PRO" />
-                            </Border>
-                        </StackPanel>
-                    </controls:SettingsExpander.Header>
-                    <controls:SettingsExpander.Description>
-                        <StackPanel Orientation="Horizontal" Spacing="4">
-                            <TextBlock
-                                Foreground="{ThemeResource TextFillColorSecondaryBrush}"
-                                Style="{StaticResource CaptionTextBlockStyle}"
-                                Text="{x:Bind domain:Translator.WinoAccount_Management_AiPackSubscriptionActive}" />
-                            <TextBlock
-                                Foreground="{ThemeResource TextFillColorSecondaryBrush}"
-                                Style="{StaticResource CaptionTextBlockStyle}"
-                                Text=" · " />
-                            <TextBlock
-                                Foreground="{ThemeResource TextFillColorSecondaryBrush}"
-                                Style="{StaticResource CaptionTextBlockStyle}"
-                                Text="{x:Bind ViewModel.AiPackRenewalText, Mode=OneWay}" />
-                        </StackPanel>
-                    </controls:SettingsExpander.Description>
-                    <HyperlinkButton Command="{x:Bind ViewModel.ManageAiPackCommand}" Content="{x:Bind domain:Translator.Buttons_Manage}" />
-                    <controls:SettingsExpander.Items>
-
-                        <!--  AI Pack active: usage bar  -->
-
-                        <controls:SettingsCard x:Name="AiPackUsageCard" HorizontalContentAlignment="Stretch">
-                            <controls:SettingsCard.Header>
-                                <StackPanel MinWidth="400" Spacing="8">
-                                    <StackPanel Orientation="Horizontal" Spacing="4">
-                                        <TextBlock
-                                            FontSize="24"
-                                            FontWeight="Bold"
-                                            Text="{x:Bind ViewModel.AiUsageCount, Mode=OneWay}" />
-                                        <TextBlock
-                                            Margin="0,0,0,2"
-                                            VerticalAlignment="Bottom"
-                                            Foreground="{ThemeResource TextFillColorSecondaryBrush}"
-                                            Style="{StaticResource CaptionTextBlockStyle}">
-                                            <Run Text="/ " />
-                                            <Run Text="{x:Bind ViewModel.AiUsageLimit, Mode=OneWay}" />
-                                        </TextBlock>
-                                    </StackPanel>
-                                    <ProgressBar
-                                        Height="8"
-                                        Maximum="100"
-                                        Value="{x:Bind ViewModel.AiUsagePercentage, Mode=OneWay}" />
-                                    <Grid>
-                                        <TextBlock
-                                            HorizontalAlignment="Left"
-                                            Foreground="{ThemeResource TextFillColorSecondaryBrush}"
-                                            Style="{StaticResource CaptionTextBlockStyle}"
-                                            Text="{x:Bind domain:Translator.WinoAccount_Management_AiPackRequestsUsed}" />
-                                        <TextBlock
-                                            HorizontalAlignment="Right"
-                                            Foreground="{ThemeResource TextFillColorSecondaryBrush}"
-                                            Style="{StaticResource CaptionTextBlockStyle}"
-                                            Text="{x:Bind ViewModel.AiUsageResetText, Mode=OneWay}" />
-                                    </Grid>
-                                </StackPanel>
-                            </controls:SettingsCard.Header>
-                        </controls:SettingsCard>
-                    </controls:SettingsExpander.Items>
-                </controls:SettingsExpander>
-
-
-
-                <!--  ─── Data section ───  -->
                 <TextBlock
                     Margin="0,12,0,4"
                     Style="{StaticResource BodyStrongTextBlockStyle}"
                     Text="{x:Bind domain:Translator.WinoAccount_Management_DataSectionHeader}" />
 
-                <controls:SettingsCard Description="{x:Bind domain:Translator.WinoAccount_Management_ImportSettingsDescription}" Header="{x:Bind domain:Translator.WinoAccount_Management_ImportSettingsTitle}">
+                <controls:SettingsCard Description="{x:Bind domain:Translator.WinoAccount_Management_SyncPreferencesDescription}" Header="{x:Bind domain:Translator.WinoAccount_Management_SyncPreferencesTitle}">
                     <controls:SettingsCard.HeaderIcon>
-                        <FontIcon FontFamily="{StaticResource SymbolThemeFontFamily}" Glyph="&#xE896;" />
+                        <PathIcon
+                            HorizontalAlignment="Center"
+                            VerticalAlignment="Center"
+                            Data="F1 M 18.330078 3.330078 L 18.330078 7.5 C 18.330078 7.727865 18.248697 7.923178 18.085938 8.085938 C 17.923176 8.248698 17.727863 8.330078 17.5 8.330078 L 13.330078 8.330078 C 13.102213 8.330078 12.9069 8.248698 12.744141 8.085938 C 12.58138 7.923178 12.5 7.727865 12.5 7.5 C 12.5 7.272136 12.58138 7.076823 12.744141 6.914062 C 12.9069 6.751303 13.102213 6.669923 13.330078 6.669922 L 15.78125 6.669922 C 15.481771 6.149089 15.120442 5.681967 14.697266 5.268555 C 14.274088 4.855145 13.808593 4.505209 13.300781 4.21875 C 12.792968 3.932293 12.25423 3.712566 11.68457 3.55957 C 11.114908 3.406576 10.530599 3.330078 9.931641 3.330078 C 9.384766 3.330078 8.846028 3.401693 8.31543 3.544922 C 7.784831 3.688152 7.280273 3.891602 6.801758 4.155273 C 6.323242 4.418945 5.878906 4.737956 5.46875 5.112305 C 5.058594 5.486654 4.703776 5.901693 4.404297 6.357422 C 4.254557 6.585287 4.127604 6.816407 4.023438 7.050781 C 3.919271 7.285157 3.815104 7.526043 3.710938 7.773438 C 3.639323 7.942709 3.538411 8.0778 3.408203 8.178711 C 3.277995 8.279623 3.11849 8.330078 2.929688 8.330078 C 2.701823 8.330078 2.504883 8.250326 2.338867 8.09082 C 2.172852 7.931315 2.089844 7.734375 2.089844 7.5 C 2.089844 7.415365 2.10612 7.32422 2.138672 7.226562 C 2.41862 6.412761 2.81901 5.66569 3.339844 4.985352 C 3.860677 4.305014 4.464518 3.719076 5.151367 3.227539 C 5.838216 2.736004 6.588541 2.353516 7.402344 2.080078 C 8.216146 1.806641 9.052734 1.669922 9.912109 1.669922 C 10.576172 1.669922 11.227213 1.743164 11.865234 1.889648 C 12.503255 2.036133 13.111979 2.250977 13.691406 2.53418 C 14.270832 2.817383 14.811197 3.167318 15.3125 3.583984 C 15.813802 4.000652 16.266275 4.475912 16.669922 5.009766 L 16.669922 3.330078 C 16.669922 3.102215 16.751301 2.906902 16.914062 2.744141 C 17.076822 2.581381 17.272135 2.5 17.5 2.5 C 17.727863 2.5 17.923176 2.581381 18.085938 2.744141 C 18.248697 2.906902 18.330078 3.102215 18.330078 3.330078 Z M 17.861328 12.5 C 17.861328 12.584636 17.845051 12.675781 17.8125 12.773438 C 17.532551 13.58724 17.13216 14.334311 16.611328 15.014648 C 16.090494 15.694987 15.486653 16.280924 14.799805 16.772461 C 14.112955 17.263998 13.362629 17.646484 12.548828 17.919922 C 11.735025 18.193359 10.898438 18.330078 10.039062 18.330078 C 9.375 18.330078 8.728841 18.258463 8.100586 18.115234 C 7.472331 17.972006 6.871745 17.762045 6.298828 17.485352 C 5.725911 17.208658 5.188802 16.865234 4.6875 16.455078 C 4.186198 16.044922 3.733724 15.576172 3.330078 15.048828 L 3.330078 16.669922 C 3.330078 16.897787 3.248698 17.0931 3.085938 17.255859 C 2.923177 17.418619 2.727865 17.5 2.5 17.5 C 2.272135 17.5 2.076823 17.418619 1.914062 17.255859 C 1.751302 17.0931 1.669922 16.897787 1.669922 16.669922 L 1.669922 12.5 C 1.669922 12.272136 1.751302 12.076823 1.914062 11.914062 C 2.076823 11.751303 2.272135 11.669922 2.5 11.669922 L 6.669922 11.669922 C 6.897786 11.669922 7.093099 11.751303 7.255859 11.914062 C 7.418619 12.076823 7.5 12.272136 7.5 12.5 C 7.5 12.727865 7.418619 12.923178 7.255859 13.085938 C 7.093099 13.248698 6.897786 13.330078 6.669922 13.330078 L 4.179688 13.330078 C 4.479167 13.850912 4.840495 14.318034 5.263672 14.731445 C 5.686849 15.144857 6.150716 15.494792 6.655273 15.78125 C 7.15983 16.067709 7.696939 16.287436 8.266602 16.44043 C 8.836263 16.593424 9.420572 16.669922 10.019531 16.669922 C 10.566406 16.669922 11.106771 16.598307 11.640625 16.455078 C 12.174479 16.31185 12.680664 16.108398 13.15918 15.844727 C 13.637695 15.581055 14.080403 15.262045 14.487305 14.887695 C 14.894205 14.513347 15.247396 14.095053 15.546875 13.632812 C 15.696614 13.404948 15.821939 13.173828 15.922852 12.939453 C 16.023762 12.705078 16.129557 12.464193 16.240234 12.216797 C 16.311848 12.047526 16.414387 11.912436 16.547852 11.811523 C 16.681314 11.710612 16.842447 11.660156 17.03125 11.660156 C 17.148438 11.660156 17.257486 11.682943 17.358398 11.728516 C 17.459309 11.774089 17.547199 11.834311 17.62207 11.90918 C 17.696939 11.98405 17.755533 12.07194 17.797852 12.172852 C 17.840168 12.273764 17.861328 12.382812 17.861328 12.5 Z " />
                     </controls:SettingsCard.HeaderIcon>
-                    <Button Command="{x:Bind ViewModel.ImportSettingsCommand}" Content="{x:Bind domain:Translator.Buttons_Browse}" />
+                    <StackPanel Orientation="Horizontal" Spacing="6">
+                        <Button Command="{x:Bind ViewModel.ExportSettingsCommand}" Content="{x:Bind domain:Translator.Buttons_Export}" />
+                        <Button Command="{x:Bind ViewModel.ImportSettingsCommand}" Content="{x:Bind domain:Translator.Buttons_Import}" />
+                    </StackPanel>
                 </controls:SettingsCard>
 
-                <controls:SettingsCard Description="{x:Bind domain:Translator.WinoAccount_Management_ExportSettingsDescription}" Header="{x:Bind domain:Translator.WinoAccount_Management_ExportSettingsTitle}">
-                    <controls:SettingsCard.HeaderIcon>
-                        <FontIcon FontFamily="{StaticResource SymbolThemeFontFamily}" Glyph="&#xE898;" />
-                    </controls:SettingsCard.HeaderIcon>
-                    <Button Command="{x:Bind ViewModel.ExportSettingsCommand}" Content="{x:Bind domain:Translator.Buttons_Export}" />
-                </controls:SettingsCard>
-
-                <!--  ─── Account actions section ───  -->
                 <TextBlock
                     Margin="0,12,0,4"
                     Style="{StaticResource BodyStrongTextBlockStyle}"

Wino.Services/ServicesContainerSetup.cs

@@ -29,6 +29,7 @@ public static class ServicesContainerSetup
         services.AddTransient<IKeyboardShortcutService, KeyboardShortcutService>();
         services.AddSingleton<IWinoAccountApiClient, WinoAccountApiClient>();
         services.AddTransient<IWinoAccountProfileService, WinoAccountProfileService>();
+        services.AddTransient<IWinoAddOnService, WinoAddOnService>();
         services.AddSingleton<IContactPictureFileService, ContactPictureFileService>();
 
         services.AddTransient<ICalDavClient, CalDavClient>();

Wino.Services/WinoAccountApiClient.cs

@@ -11,9 +11,12 @@ using System.Text.Json.Serialization.Metadata;
 using System.Threading;
 using System.Threading.Tasks;
 using Wino.Core.Domain.Entities.Shared;
+using Wino.Core.Domain.Enums;
 using Wino.Core.Domain.Interfaces;
+using Wino.Core.Domain.Models.Accounts;
 using Wino.Mail.Api.Contracts.Ai;
 using Wino.Mail.Api.Contracts.Auth;
+using Wino.Mail.Api.Contracts.Billing;
 using Wino.Mail.Api.Contracts.Common;
 
 namespace Wino.Services;
@@ -46,13 +49,13 @@ public sealed class WinoAccountApiClient : IWinoAccountApiClient, IDisposable
         _ownsHttpClient = true;
     }
 
-    public Task<ApiEnvelope<AuthResultDto>> RegisterAsync(string email, string password, CancellationToken cancellationToken = default)
+    public Task<WinoAccountApiResult<AuthResultDto>> RegisterAsync(string email, string password, CancellationToken cancellationToken = default)
         => SendAuthRequestAsync("api/v1/auth/register", new RegisterRequest(email, password), WinoAccountApiJsonContext.Default.RegisterRequest, cancellationToken);
 
-    public Task<ApiEnvelope<AuthResultDto>> LoginAsync(string email, string password, CancellationToken cancellationToken = default)
+    public Task<WinoAccountApiResult<AuthResultDto>> LoginAsync(string email, string password, CancellationToken cancellationToken = default)
         => SendAuthRequestAsync("api/v1/auth/login", new LoginRequest(email, password), WinoAccountApiJsonContext.Default.LoginRequest, cancellationToken);
 
-    public Task<ApiEnvelope<AuthResultDto>> RefreshAsync(string refreshToken, CancellationToken cancellationToken = default)
+    public Task<WinoAccountApiResult<AuthResultDto>> RefreshAsync(string refreshToken, CancellationToken cancellationToken = default)
         => SendAuthRequestAsync("api/v1/auth/refresh", new RefreshRequest(refreshToken), WinoAccountApiJsonContext.Default.RefreshRequest, cancellationToken);
 
     public async Task<ApiEnvelope<JsonElement>> LogoutAsync(string refreshToken, CancellationToken cancellationToken = default)
@@ -84,20 +87,27 @@ public sealed class WinoAccountApiClient : IWinoAccountApiClient, IDisposable
     public Task<ApiEnvelope<AiStatusResultDto>> GetAiStatusAsync(CancellationToken cancellationToken = default)
         => SendAuthorizedRequestAsync("api/v1/ai/status", WinoAccountApiJsonContext.Default.ApiEnvelopeAiStatusResultDto, cancellationToken);
 
-    public Task<ApiEnvelope<string>> CreateCheckoutSessionAsync(string productId, CancellationToken cancellationToken = default)
+    public Task<ApiEnvelope<CheckoutSessionResultDto>> CreateCheckoutSessionAsync(WinoAddOnProductType productId, CancellationToken cancellationToken = default)
     {
         var endpoint = productId switch
         {
-            "ai-pack-monthly" => "api/v1/billing/ai-pack/checkout-session",
+            WinoAddOnProductType.AI_PACK => "api/v1/billing/ai-pack/checkout-session",
-            "unlimited-accounts" => "api/v1/billing/unlimited-accounts/checkout-session",
+            WinoAddOnProductType.UNLIMITED_ACCOUNTS => "api/v1/billing/unlimited-accounts/checkout-session",
             _ => string.Empty
         };
 
         return string.IsNullOrWhiteSpace(endpoint)
-            ? Task.FromResult(ApiEnvelope<string>.Failure("UnknownProduct"))
+            ? Task.FromResult(ApiEnvelope<CheckoutSessionResultDto>.Failure("UnknownProduct"))
-            : SendAuthorizedRequestAsync(HttpMethod.Post, endpoint, WinoAccountApiJsonContext.Default.ApiEnvelopeString, cancellationToken);
+            : SendAuthorizedRequestAsync(HttpMethod.Post, endpoint, WinoAccountApiJsonContext.Default.ApiEnvelopeCheckoutSessionResultDto, cancellationToken);
     }
 
+    public Task<ApiEnvelope<CustomerPortalResultDto>> CreateCustomerPortalSessionAsync(CancellationToken cancellationToken = default)
+        => SendAuthorizedRequestAsync(
+            HttpMethod.Post,
+            "api/v1/billing/ai-pack/customer-portal-session",
+            WinoAccountApiJsonContext.Default.ApiEnvelopeCustomerPortalResultDto,
+            cancellationToken);
+
     public async Task<string?> GetSettingsAsync(CancellationToken cancellationToken = default)
     {
         try
@@ -141,7 +151,7 @@ public sealed class WinoAccountApiClient : IWinoAccountApiClient, IDisposable
         }
     }
 
-    private async Task<ApiEnvelope<AuthResultDto>> SendAuthRequestAsync<TRequest>(string endpoint, TRequest request, JsonTypeInfo<TRequest> typeInfo, CancellationToken cancellationToken)
+    private async Task<WinoAccountApiResult<AuthResultDto>> SendAuthRequestAsync<TRequest>(string endpoint, TRequest request, JsonTypeInfo<TRequest> typeInfo, CancellationToken cancellationToken)
     {
         try
         {
@@ -156,14 +166,83 @@ public sealed class WinoAccountApiClient : IWinoAccountApiClient, IDisposable
                 ? null
                 : JsonSerializer.Deserialize(payload, WinoAccountApiJsonContext.Default.ApiEnvelopeAuthResultDto);
 
-            return envelope ?? ApiEnvelope<AuthResultDto>.Failure($"HTTP {(int)response.StatusCode} {response.ReasonPhrase}".Trim());
+            if (envelope?.IsSuccess == true && envelope.Result != null)
+            {
+                return WinoAccountApiResult<AuthResultDto>.Success(envelope.Result);
+            }
+
+            var errorCode = envelope?.ErrorCode ?? $"HTTP {(int)response.StatusCode} {response.ReasonPhrase}".Trim();
+            var errorMessage = ExtractErrorMessage(payload) ?? response.ReasonPhrase;
+
+            return WinoAccountApiResult<AuthResultDto>.Failure(errorCode, errorMessage);
         }
         catch (Exception ex)
         {
-            return ApiEnvelope<AuthResultDto>.Failure(ex.Message);
+            return WinoAccountApiResult<AuthResultDto>.Failure(ex.GetType().Name, ex.Message);
         }
     }
 
+    private static string? ExtractErrorMessage(string? payload)
+    {
+        if (string.IsNullOrWhiteSpace(payload))
+        {
+            return null;
+        }
+
+        try
+        {
+            using var document = JsonDocument.Parse(payload);
+            return TryGetErrorMessage(document.RootElement);
+        }
+        catch (JsonException)
+        {
+            return null;
+        }
+    }
+
+    private static string? TryGetErrorMessage(JsonElement element)
+    {
+        if (TryGetStringProperty(element, "errorMessage", out var errorMessage))
+        {
+            return errorMessage;
+        }
+
+        if (TryGetStringProperty(element, "message", out var message))
+        {
+            return message;
+        }
+
+        if (TryGetStringProperty(element, "detail", out var detail))
+        {
+            return detail;
+        }
+
+        if (element.ValueKind == JsonValueKind.Object && element.TryGetProperty("error", out var errorElement))
+        {
+            return TryGetErrorMessage(errorElement);
+        }
+
+        return null;
+    }
+
+    private static bool TryGetStringProperty(JsonElement element, string propertyName, out string? value)
+    {
+        value = null;
+
+        if (element.ValueKind != JsonValueKind.Object || !element.TryGetProperty(propertyName, out var property))
+        {
+            return false;
+        }
+
+        if (property.ValueKind != JsonValueKind.String)
+        {
+            return false;
+        }
+
+        value = property.GetString();
+        return !string.IsNullOrWhiteSpace(value);
+    }
+
     private Task<ApiEnvelope<TResponse>> SendAuthorizedRequestAsync<TResponse>(string endpoint, JsonTypeInfo<ApiEnvelope<TResponse>> typeInfo, CancellationToken cancellationToken)
         => SendAuthorizedRequestAsync(HttpMethod.Get, endpoint, typeInfo, cancellationToken);
 
@@ -234,6 +313,7 @@ public sealed class WinoAccountApiClient : IWinoAccountApiClient, IDisposable
 [JsonSerializable(typeof(ApiEnvelope<AuthResultDto>))]
 [JsonSerializable(typeof(ApiEnvelope<AuthUserDto>))]
 [JsonSerializable(typeof(ApiEnvelope<AiStatusResultDto>))]
-[JsonSerializable(typeof(ApiEnvelope<string>))]
+[JsonSerializable(typeof(ApiEnvelope<CheckoutSessionResultDto>))]
+[JsonSerializable(typeof(ApiEnvelope<CustomerPortalResultDto>))]
 [JsonSerializable(typeof(ApiEnvelope<JsonElement>))]
 internal sealed partial class WinoAccountApiJsonContext : JsonSerializerContext;

Wino.Services/WinoAccountProfileService.cs

@@ -1,13 +1,16 @@
 #nullable enable
 using System;
+using System.Reflection;
 using System.Threading;
 using System.Threading.Tasks;
 using Serilog;
 using Wino.Core.Domain.Entities.Shared;
+using Wino.Core.Domain.Enums;
 using Wino.Core.Domain.Interfaces;
 using Wino.Core.Domain.Models.Accounts;
 using Wino.Mail.Api.Contracts.Ai;
 using Wino.Mail.Api.Contracts.Auth;
+using Wino.Mail.Api.Contracts.Billing;
 using Wino.Mail.Api.Contracts.Common;
 using Wino.Messaging.UI;
 
@@ -16,11 +19,15 @@ namespace Wino.Services;
 public sealed class WinoAccountProfileService : BaseDatabaseService, IWinoAccountProfileService
 {
     private readonly IWinoAccountApiClient _apiClient;
+    private readonly IStoreManagementService _storeManagementService;
     private readonly ILogger _logger = Log.ForContext<WinoAccountProfileService>();
 
-    public WinoAccountProfileService(IDatabaseService databaseService, IWinoAccountApiClient apiClient) : base(databaseService)
+    public WinoAccountProfileService(IDatabaseService databaseService,
+                                     IWinoAccountApiClient apiClient,
+                                     IStoreManagementService storeManagementService) : base(databaseService)
     {
         _apiClient = apiClient;
+        _storeManagementService = storeManagementService;
     }
 
     public async Task<WinoAccountOperationResult> RegisterAsync(string email, string password, CancellationToken cancellationToken = default)
@@ -108,6 +115,16 @@ public sealed class WinoAccountProfileService : BaseDatabaseService, IWinoAccoun
     public async Task<bool> HasActiveAccountAsync()
         => await Connection.Table<WinoAccount>().CountAsync().ConfigureAwait(false) > 0;
 
+    public async Task<bool> HasAddOnAsync(WinoAddOnProductType productId, CancellationToken cancellationToken = default)
+    {
+        return productId switch
+        {
+            WinoAddOnProductType.AI_PACK => await HasAiPackAsync(cancellationToken).ConfigureAwait(false),
+            WinoAddOnProductType.UNLIMITED_ACCOUNTS => await HasUnlimitedAccountsAsync(cancellationToken).ConfigureAwait(false),
+            _ => false
+        };
+    }
+
     public async Task<ApiEnvelope<AuthUserDto>> GetCurrentUserAsync(CancellationToken cancellationToken = default)
     {
         var account = await GetAuthenticatedAccountAsync(cancellationToken).ConfigureAwait(false);
@@ -142,12 +159,12 @@ public sealed class WinoAccountProfileService : BaseDatabaseService, IWinoAccoun
         return response;
     }
 
-    public async Task<ApiEnvelope<string>> CreateCheckoutSessionAsync(string productId, CancellationToken cancellationToken = default)
+    public async Task<ApiEnvelope<CheckoutSessionResultDto>> CreateCheckoutSessionAsync(WinoAddOnProductType productId, CancellationToken cancellationToken = default)
     {
         var account = await GetAuthenticatedAccountAsync(cancellationToken).ConfigureAwait(false);
         if (account == null)
         {
-            return ApiEnvelope<string>.Failure("MissingAccessToken");
+            return ApiEnvelope<CheckoutSessionResultDto>.Failure("MissingAccessToken");
         }
 
         var response = await _apiClient.CreateCheckoutSessionAsync(productId, cancellationToken).ConfigureAwait(false);
@@ -159,6 +176,23 @@ public sealed class WinoAccountProfileService : BaseDatabaseService, IWinoAccoun
         return response;
     }
 
+    public async Task<ApiEnvelope<CustomerPortalResultDto>> CreateCustomerPortalSessionAsync(CancellationToken cancellationToken = default)
+    {
+        var account = await GetAuthenticatedAccountAsync(cancellationToken).ConfigureAwait(false);
+        if (account == null)
+        {
+            return ApiEnvelope<CustomerPortalResultDto>.Failure("MissingAccessToken");
+        }
+
+        var response = await _apiClient.CreateCustomerPortalSessionAsync(cancellationToken).ConfigureAwait(false);
+        if (!response.IsSuccess)
+        {
+            _logger.Warning("Failed to create customer portal session for Wino account {Email}. Error code: {ErrorCode}", account.Email, response.ErrorCode);
+        }
+
+        return response;
+    }
+
     public async Task SignOutAsync(CancellationToken cancellationToken = default)
     {
         var account = await GetActiveAccountAsync().ConfigureAwait(false);
@@ -187,12 +221,12 @@ public sealed class WinoAccountProfileService : BaseDatabaseService, IWinoAccoun
         }
     }
 
-    private async Task<WinoAccountOperationResult> PersistResponseAsync(ApiEnvelope<AuthResultDto> response)
+    private async Task<WinoAccountOperationResult> PersistResponseAsync(WinoAccountApiResult<AuthResultDto> response)
     {
         if (!response.IsSuccess || response.Result == null)
         {
-            _logger.Warning("Wino account operation failed. Error code: {ErrorCode}", response.ErrorCode);
+            _logger.Warning("Wino account operation failed. Error code: {ErrorCode}. Error message: {ErrorMessage}", response.ErrorCode, response.ErrorMessage);
-            return WinoAccountOperationResult.Failure(response.ErrorCode);
+            return WinoAccountOperationResult.Failure(response.ErrorCode, response.ErrorMessage);
         }
 
         var account = Map(response.Result);
@@ -203,6 +237,48 @@ public sealed class WinoAccountProfileService : BaseDatabaseService, IWinoAccoun
         return WinoAccountOperationResult.Success(account);
     }
 
+    private async Task<bool> HasAiPackAsync(CancellationToken cancellationToken)
+    {
+        var response = await GetAiStatusAsync(cancellationToken).ConfigureAwait(false);
+        return response.IsSuccess && response.Result?.HasAiPack == true;
+    }
+
+    private async Task<bool> HasUnlimitedAccountsAsync(CancellationToken cancellationToken)
+    {
+        if (await HasRemoteUnlimitedAccountsAsync(cancellationToken).ConfigureAwait(false))
+        {
+            return true;
+        }
+
+        return await _storeManagementService.HasProductAsync(WinoAddOnProductType.UNLIMITED_ACCOUNTS).ConfigureAwait(false);
+    }
+
+    private async Task<bool> HasRemoteUnlimitedAccountsAsync(CancellationToken cancellationToken)
+    {
+        var response = await GetCurrentUserAsync(cancellationToken).ConfigureAwait(false);
+        if (!response.IsSuccess || response.Result == null)
+        {
+            return false;
+        }
+
+        return TryGetBooleanProperty(response.Result, "HasUnlimitedAccounts", out var hasUnlimitedAccounts) && hasUnlimitedAccounts;
+    }
+
+    [System.Diagnostics.CodeAnalysis.UnconditionalSuppressMessage("Trimming", "IL2075", Justification = "The reflected contract property is a stable API field read from a concrete DTO instance.")]
+    private static bool TryGetBooleanProperty(object instance, string propertyName, out bool value)
+    {
+        value = false;
+
+        var property = instance.GetType().GetProperty(propertyName, BindingFlags.Instance | BindingFlags.Public);
+        if (property?.PropertyType != typeof(bool))
+        {
+            return false;
+        }
+
+        value = (bool)(property.GetValue(instance) ?? false);
+        return true;
+    }
+
     private static WinoAccount Map(AuthResultDto result)
         => new()
         {

Wino.Services/WinoAddOnService.cs

@@ -0,0 +1,52 @@
+#nullable enable
+using System.Collections.Generic;
+using System.Threading;
+using System.Threading.Tasks;
+using Wino.Core.Domain.Enums;
+using Wino.Core.Domain.Interfaces;
+using Wino.Core.Domain.Models.Accounts;
+
+namespace Wino.Services;
+
+public sealed class WinoAddOnService : IWinoAddOnService
+{
+    private static readonly WinoAddOnProductType[] AvailableAddOns =
+    [
+        WinoAddOnProductType.AI_PACK,
+        WinoAddOnProductType.UNLIMITED_ACCOUNTS
+    ];
+
+    private readonly IWinoAccountProfileService _profileService;
+
+    public WinoAddOnService(IWinoAccountProfileService profileService)
+    {
+        _profileService = profileService;
+    }
+
+    public async Task<IReadOnlyList<WinoAddOnInfo>> GetAvailableAddOnsAsync(CancellationToken cancellationToken = default)
+    {
+        var aiStatusTask = _profileService.GetAiStatusAsync(cancellationToken);
+        var hasUnlimitedAccountsTask = _profileService.HasAddOnAsync(WinoAddOnProductType.UNLIMITED_ACCOUNTS, cancellationToken);
+
+        await Task.WhenAll(aiStatusTask, hasUnlimitedAccountsTask).ConfigureAwait(false);
+
+        var aiStatusResponse = await aiStatusTask.ConfigureAwait(false);
+        var aiStatus = aiStatusResponse.IsSuccess ? aiStatusResponse.Result : null;
+
+        return
+        [
+            new WinoAddOnInfo(
+                WinoAddOnProductType.AI_PACK,
+                aiStatus?.HasAiPack == true,
+                aiStatus?.Used,
+                aiStatus?.MonthlyLimit,
+                aiStatus?.HasAiPack == true && aiStatus.MonthlyLimit is int limit && limit > 0 && aiStatus.Used is int used
+                    ? (double)used / limit * 100
+                    : 0,
+                aiStatus?.CurrentPeriodEndUtc),
+            new WinoAddOnInfo(
+                WinoAddOnProductType.UNLIMITED_ACCOUNTS,
+                await hasUnlimitedAccountsTask.ConfigureAwait(false))
+        ];
+    }
+}