Add read receipt tracking for sent mail

Wino.Core.Tests/Helpers/InMemoryDatabaseService.cs

@@ -50,6 +50,7 @@ public class InMemoryDatabaseService : IDatabaseService
         await Connection.CreateTableAsync<CalendarAttachment>();
         await Connection.CreateTableAsync<Reminder>();
         await Connection.CreateTableAsync<MailInvitationCalendarMapping>();
+        await Connection.CreateTableAsync<SentMailReceiptState>();
         await Connection.CreateTableAsync<WinoAccount>();
     }
 

Wino.Core.Tests/Services/MailFetchingTests.cs

@@ -370,6 +370,7 @@ public class MailFetchingTests : IAsyncLifetime
 
         var folderService = new FolderService(db, accountService);
         var contactService = new ContactService(db);
+        var sentMailReceiptService = new SentMailReceiptService(db, folderService, accountService);
 
         return new MailService(
             db,
@@ -378,6 +379,7 @@ public class MailFetchingTests : IAsyncLifetime
             accountService,
             signatureService.Object,
             mimeFileService.Object,
-            preferencesService.Object);
+            preferencesService.Object,
+            sentMailReceiptService);
     }
 }

Wino.Core.Tests/Services/MailThreadingTests.cs

@@ -230,6 +230,7 @@ public class MailThreadingTests : IAsyncLifetime
 
         var folderService = new FolderService(db, accountService);
         var contactService = new ContactService(db);
+        var sentMailReceiptService = new SentMailReceiptService(db, folderService, accountService);
 
         return new MailService(
             db,
@@ -238,6 +239,7 @@ public class MailThreadingTests : IAsyncLifetime
             accountService,
             signatureService.Object,
             mimeFileService.Object,
-            preferencesService.Object);
+            preferencesService.Object,
+            sentMailReceiptService);
     }
 }

Wino.Core.Tests/Services/ReadReceiptTrackingTests.cs

@@ -0,0 +1,151 @@
+using FluentAssertions;
+using MimeKit;
+using Moq;
+using System.IO;
+using System.Text;
+using Wino.Core.Domain;
+using Wino.Core.Domain.Entities.Mail;
+using Wino.Core.Domain.Entities.Shared;
+using Wino.Core.Domain.Enums;
+using Wino.Core.Domain.Extensions;
+using Wino.Core.Domain.Interfaces;
+using Wino.Core.Extensions;
+using Wino.Core.Tests.Helpers;
+using Wino.Services;
+using Xunit;
+
+namespace Wino.Core.Tests.Services;
+
+public sealed class ReadReceiptTrackingTests
+{
+    [Fact]
+    public void SetReadReceiptRequest_WhenEnabled_AddsDispositionNotificationHeader()
+    {
+        var mime = new MimeMessage();
+
+        mime.SetReadReceiptRequest("sender@example.com", true);
+
+        mime.HasReadReceiptRequest().Should().BeTrue();
+        mime.Headers[Constants.DispositionNotificationToHeader].Should().Be("sender@example.com");
+    }
+
+    [Fact]
+    public void SetReadReceiptRequest_WhenDisabled_RemovesDispositionNotificationHeader()
+    {
+        var mime = new MimeMessage();
+        mime.Headers.Add(Constants.DispositionNotificationToHeader, "sender@example.com");
+
+        mime.SetReadReceiptRequest("sender@example.com", false);
+
+        mime.HasReadReceiptRequest().Should().BeFalse();
+    }
+
+    [Fact]
+    public void ParseReadReceipt_ExtractsOriginalMessageIdAndAcknowledgedTime()
+    {
+        var mime = new MimeMessage
+        {
+            Date = new DateTimeOffset(2026, 04, 10, 12, 30, 0, TimeSpan.Zero),
+            Body = CreateDispositionNotificationBody("Final-Recipient: rfc822; recipient@example.com\r\nOriginal-Message-ID: <original@example.com>\r\nDisposition: manual-action/MDN-sent-manually; displayed\r\n")
+        };
+
+        var result = mime.ParseReadReceipt();
+
+        result.IsReadReceipt.Should().BeTrue();
+        result.OriginalMessageId.Should().Be("original@example.com");
+        result.AcknowledgedAtUtc.Should().Be(new DateTime(2026, 04, 10, 12, 30, 0, DateTimeKind.Utc));
+    }
+
+    [Fact]
+    public void AsOutlookMessage_WhenMimeRequestsReadReceipt_SetsGraphFlag()
+    {
+        var mime = new MimeMessage
+        {
+            Subject = "Test receipt request",
+            Body = new TextPart("plain") { Text = "Hello" }
+        };
+        mime.MessageId = "test@example.com";
+        mime.From.Add(new MailboxAddress("Sender", "sender@example.com"));
+        mime.To.Add(new MailboxAddress("Recipient", "recipient@example.com"));
+        mime.SetReadReceiptRequest("sender@example.com", true);
+
+        var message = mime.AsOutlookMessage(includeInternetHeaders: false);
+
+        message.IsReadReceiptRequested.Should().BeTrue();
+    }
+
+    [Fact]
+    public async Task ProcessIncomingReceiptAsync_MatchesSentMailByMessageId_AndAcknowledgesState()
+    {
+        var db = new InMemoryDatabaseService();
+        await db.InitializeAsync();
+
+        var account = new MailAccount
+        {
+            Id = Guid.NewGuid(),
+            Address = "sender@example.com",
+            SenderName = "Sender"
+        };
+
+        var sentFolder = new MailItemFolder
+        {
+            Id = Guid.NewGuid(),
+            MailAccountId = account.Id,
+            FolderName = "Sent",
+            SpecialFolderType = SpecialFolderType.Sent
+        };
+
+        var sentMail = new MailCopy
+        {
+            UniqueId = Guid.NewGuid(),
+            Id = "sent-1",
+            FolderId = sentFolder.Id,
+            MessageId = "original@example.com",
+            CreationDate = new DateTime(2026, 04, 10, 10, 0, 0, DateTimeKind.Utc)
+        };
+
+        await db.Connection.InsertAsync(account, typeof(MailAccount));
+        await db.Connection.InsertAsync(sentFolder, typeof(MailItemFolder));
+        await db.Connection.InsertAsync(sentMail, typeof(MailCopy));
+
+        var folderService = new Mock<IFolderService>(MockBehavior.Strict);
+        folderService.Setup(x => x.GetFolderAsync(sentFolder.Id)).ReturnsAsync(sentFolder);
+
+        var accountService = new Mock<IAccountService>(MockBehavior.Strict);
+        accountService.Setup(x => x.GetAccountAsync(account.Id)).ReturnsAsync(account);
+
+        var service = new SentMailReceiptService(db, folderService.Object, accountService.Object);
+
+        var receiptMail = new MailCopy
+        {
+            UniqueId = Guid.NewGuid(),
+            AssignedAccount = account
+        };
+
+        var receiptMime = new MimeMessage
+        {
+            Date = new DateTimeOffset(2026, 04, 10, 13, 15, 0, TimeSpan.Zero),
+            Body = CreateDispositionNotificationBody("Original-Message-ID: <original@example.com>\r\nDisposition: manual-action/MDN-sent-manually; displayed\r\n")
+        };
+
+        await service.ProcessIncomingReceiptAsync(receiptMail, receiptMime);
+
+        var receiptState = await db.Connection.FindAsync<SentMailReceiptState>(sentMail.UniqueId);
+        receiptState.Should().NotBeNull();
+        receiptState!.Status.Should().Be(SentMailReceiptStatus.Acknowledged);
+        receiptState.ReceiptMessageUniqueId.Should().Be(receiptMail.UniqueId);
+        receiptState.MessageId.Should().Be("original@example.com");
+    }
+
+    private static Multipart CreateDispositionNotificationBody(string dispositionText)
+    {
+        var report = new Multipart("report");
+        report.ContentType.Parameters.Add("report-type", "disposition-notification");
+        report.Add(new TextPart("plain") { Text = "Read receipt" });
+        report.Add(new MimePart("message", "disposition-notification")
+        {
+            Content = new MimeContent(new MemoryStream(Encoding.UTF8.GetBytes(dispositionText)))
+        });
+        return report;
+    }
+}