Fix voice message forwarding and playback

2026-07-14 14:53:18 +03:00
parent edf108f621
commit 8e9a4c1151
13 changed files with 618 additions and 37 deletions
@@ -686,8 +686,12 @@ async def normalize_attachment(client: Client, message: Any, att: Any, sort_orde
            req = await client.get_video_by_id(int(chat_id), int(message_id), int(data["video_id"]))
            req_data = dump_model(req)
            remote_url = req_data.get("url") or remote_url
-    except Exception:  # noqa: BLE001
-        pass
+    except Exception as exc:  # noqa: BLE001
+        print(
+            f"Failed to resolve MAX {kind} download URL "
+            f"(chat_id={chat_id}, message_id={message_id}): {type(exc).__name__}: {exc}",
+            flush=True,
+        )

    if kind == "photo":
        content_type = "image/jpeg"
@@ -1247,6 +1251,24 @@ async def send_attachment(request: web.Request) -> web.Response:
    return json_response({"success": bool(external_id), "externalMessageId": external_id or None, "error": None if external_id else "PyMax returned no message id.", "chatUrl": f"pymax://chat/{chat_id}"})


+@route_errors
+async def forward_message(request: web.Request) -> web.Response:
+    data = await read_json(request)
+    client = await runtime.get_client()
+    chat_id = parse_chat_id(data.get("externalChatId"))
+    source_chat_id = parse_chat_id(data.get("sourceExternalChatId"))
+    source_message_id = str(data.get("sourceExternalMessageId") or "").strip()
+    if not source_message_id:
+        raise ValueError("sourceExternalMessageId is required")
+    sent = await client.forward_message(
+        chat_id=chat_id,
+        message_id=source_message_id,
+        source_chat_id=source_chat_id,
+    )
+    external_id = clean_id(getattr(sent, "id", None))
+    return json_response({"success": bool(external_id), "externalMessageId": external_id or None, "error": None if external_id else "PyMax returned no forwarded message id.", "chatUrl": f"pymax://chat/{chat_id}"})
+
+
@route_errors
 async def media_fetch(request: web.Request) -> web.StreamResponse:
    remote_url = request.query.get("url")
@@ -1297,6 +1319,7 @@ def create_app() -> web.Application:
    app.router.add_post("/chat/delete", chat_delete)
    app.router.add_post("/send/text", send_text)
    app.router.add_post("/send/attachment", send_attachment)
+    app.router.add_post("/message/forward", forward_message)
    app.router.add_post("/message/edit", disabled_action)
    app.router.add_post("/message/delete", disabled_action)
    app.router.add_post("/message/reaction", disabled_action)
@@ -680,6 +680,8 @@ public sealed class ChatsController(
            Direction = MessageDirection.Outgoing,
            Text = source.Text,
            ForwardedFrom = ResolveForwardedFrom(source),
+            ForwardedFromExternalChatId = source.ExternalId is null ? null : source.Chat?.ExternalId,
+            ForwardedFromExternalMessageId = source.ExternalId,
            SentAt = DateTimeOffset.UtcNow,
            DeliveryState = MessageDeliveryState.Sending,
            SenderName = "You"
@@ -15,6 +15,8 @@ public sealed class Message
    public DateTimeOffset? DeletedAt { get; set; }
    public Guid? ReplyToMessageId { get; set; }
    public string? ForwardedFrom { get; set; }
+    public string? ForwardedFromExternalChatId { get; set; }
+    public string? ForwardedFromExternalMessageId { get; set; }
    public MessageDeliveryState DeliveryState { get; set; } = MessageDeliveryState.Sent;
    public string? Error { get; set; }
    public string? MediaAlbumId { get; set; }
@@ -80,7 +80,24 @@ public static class QMaxDatabaseCleanup
            WHERE message.Direction = 'Outgoing'
              AND localAttachment.Id <> remoteAttachment.Id
              AND localAttachment.SortOrder = remoteAttachment.SortOrder
-              AND localAttachment.Kind = remoteAttachment.Kind
+              AND (
+                  localAttachment.Kind = remoteAttachment.Kind OR
+                  (
+                      localAttachment.Kind = 'VoiceNote'
+                      AND remoteAttachment.Kind = 'File'
+                      AND localAttachment.FileSizeBytes = remoteAttachment.FileSizeBytes
+                      AND (
+                          lower(remoteAttachment.ContentType) LIKE 'audio/%' OR
+                          lower(remoteAttachment.OriginalFileName) LIKE '%.m4a' OR
+                          lower(remoteAttachment.OriginalFileName) LIKE '%.ogg' OR
+                          lower(remoteAttachment.OriginalFileName) LIKE '%.opus' OR
+                          lower(remoteAttachment.OriginalFileName) LIKE '%.aac' OR
+                          lower(remoteAttachment.OriginalFileName) LIKE '%.mp3' OR
+                          lower(remoteAttachment.OriginalFileName) LIKE '%.wav' OR
+                          lower(remoteAttachment.OriginalFileName) LIKE '%.flac'
+                      )
+                  )
+              )
              AND (localAttachment.ExternalId IS NULL OR trim(localAttachment.ExternalId) = '')
              AND (localAttachment.RemoteUrl IS NULL OR trim(localAttachment.RemoteUrl) = '')
              AND localAttachment.StorageFileName NOT LIKE 'remote-%'
@@ -32,6 +32,14 @@ public interface IMaxBridgeClient
    Task<MaxActionResult> DeleteChatAsync(string externalChatId, string? chatUrl, CancellationToken cancellationToken);
    Task<MaxSendResult> SendTextAsync(string externalChatId, string? chatUrl, string text, CancellationToken cancellationToken);
    Task<MaxSendResult> SendAttachmentAsync(string externalChatId, string? chatUrl, string path, string caption, CancellationToken cancellationToken);
+    Task<MaxSendResult> ForwardMessageAsync(
+        string externalChatId,
+        string sourceExternalChatId,
+        string sourceExternalMessageId,
+        CancellationToken cancellationToken)
+    {
+        return Task.FromResult(new MaxSendResult(false, null, "Native forwarding is not supported."));
+    }
    Task<MaxActionResult> EditMessageAsync(string externalChatId, string externalMessageId, string? currentText, string text, CancellationToken cancellationToken);
    Task<MaxActionResult> DeleteMessageAsync(string externalChatId, string externalMessageId, string? currentText, CancellationToken cancellationToken);
    Task<MaxActionResult> SetReactionAsync(string externalChatId, string externalMessageId, string? currentText, string emoji, CancellationToken cancellationToken);
@@ -106,6 +106,15 @@ public sealed class MockMaxBridgeClient : IMaxBridgeClient
        return Task.FromResult(new MaxSendResult(true, $"mock-file-{Guid.NewGuid():N}", null, MockChatUrl(externalChatId)));
    }

+    public Task<MaxSendResult> ForwardMessageAsync(
+        string externalChatId,
+        string sourceExternalChatId,
+        string sourceExternalMessageId,
+        CancellationToken cancellationToken)
+    {
+        return Task.FromResult(new MaxSendResult(true, $"mock-forward-{Guid.NewGuid():N}", null, MockChatUrl(externalChatId)));
+    }
+
    public Task<MaxActionResult> EditMessageAsync(string externalChatId, string externalMessageId, string? currentText, string text, CancellationToken cancellationToken)
    {
        return Task.FromResult(new MaxActionResult(true, null));
@@ -132,6 +132,20 @@ public sealed class WorkerMaxBridgeClient(
            ?? new MaxSendResult(false, null, "Worker returned an empty attachment result.");
    }

+    public async Task<MaxSendResult> ForwardMessageAsync(
+        string externalChatId,
+        string sourceExternalChatId,
+        string sourceExternalMessageId,
+        CancellationToken cancellationToken)
+    {
+        return await SendAsync<MaxSendResult>(
+                HttpMethod.Post,
+                "/message/forward",
+                new { externalChatId, sourceExternalChatId, sourceExternalMessageId },
+                cancellationToken)
+            ?? new MaxSendResult(false, null, "Worker returned an empty forward result.");
+    }
+
    public async Task<MaxActionResult> EditMessageAsync(string externalChatId, string externalMessageId, string? currentText, string text, CancellationToken cancellationToken)
    {
        return await SendAsync<MaxActionResult>(
@@ -128,8 +128,9 @@ public sealed class AttachmentStorageService(IOptions<QMaxOptions> options) : IA
            throw new InvalidOperationException($"File is larger than {_options.MaxUploadBytes} bytes.");
        }

-        var resolvedContentType = string.IsNullOrWhiteSpace(contentType) ? "application/octet-stream" : contentType;
-        var resolvedKind = preferredKind ?? GuessKind(resolvedContentType, extension);
+        var declaredContentType = string.IsNullOrWhiteSpace(contentType) ? "application/octet-stream" : contentType;
+        var resolvedKind = preferredKind ?? GuessKind(declaredContentType, extension);
+        var resolvedContentType = NormalizeContentType(declaredContentType, safeOriginalName, resolvedKind);
        var hash = await ComputeSha256Async(partPath, cancellationToken);
        File.Move(partPath, finalPath, false);

@@ -167,6 +168,32 @@ public sealed class AttachmentStorageService(IOptions<QMaxOptions> options) : IA
        return AttachmentKind.File;
    }

+    public static string NormalizeContentType(string? contentType, string? fileName, AttachmentKind kind)
+    {
+        var declared = contentType?.Trim();
+        if (!string.IsNullOrWhiteSpace(declared) &&
+            !declared.Equals("application/octet-stream", StringComparison.OrdinalIgnoreCase) &&
+            !declared.Equals("binary/octet-stream", StringComparison.OrdinalIgnoreCase))
+        {
+            return declared;
+        }
+
+        var extension = Path.GetExtension(fileName ?? "").ToLowerInvariant();
+        var inferred = extension switch
+        {
+            ".m4a" => "audio/mp4",
+            ".ogg" or ".oga" => "audio/ogg",
+            ".opus" => "audio/opus",
+            ".aac" => "audio/aac",
+            ".mp3" => "audio/mpeg",
+            ".wav" => "audio/wav",
+            ".flac" => "audio/flac",
+            _ => null
+        };
+
+        return inferred ?? (kind == AttachmentKind.VoiceNote ? "audio/ogg" : declared ?? "application/octet-stream");
+    }
+
    public static string NormalizeRemoteFileName(string? fileName, string? contentType, AttachmentKind? preferredKind)
    {
        var original = string.IsNullOrWhiteSpace(fileName) ? "" : Path.GetFileName(fileName.Trim());
@@ -7,6 +7,7 @@ using Microsoft.Extensions.Options;
 using Microsoft.IdentityModel.Tokens;
 using QMax.Api.Configuration;
 using QMax.Api.Data;
+using QMax.Api.Data.Entities;
 using QMax.Api.Infrastructure.Auth;
 using QMax.Api.Infrastructure.Hubs;
 using QMax.Api.Infrastructure.Max;
@@ -234,6 +235,27 @@ static async Task EnsureCompatibilitySchemaAsync(QMaxDbContext db)
        await db.Database.ExecuteSqlRawAsync("ALTER TABLE Chats ADD COLUMN PendingMaxActionError TEXT;");
    }

+    var messageColumns = new HashSet<string>(StringComparer.OrdinalIgnoreCase);
+    await using (var command = connection.CreateCommand())
+    {
+        command.CommandText = "PRAGMA table_info(Messages);";
+        await using var reader = await command.ExecuteReaderAsync();
+        while (await reader.ReadAsync())
+        {
+            messageColumns.Add(reader.GetString(1));
+        }
+    }
+
+    if (!messageColumns.Contains("ForwardedFromExternalChatId"))
+    {
+        await db.Database.ExecuteSqlRawAsync("ALTER TABLE Messages ADD COLUMN ForwardedFromExternalChatId TEXT;");
+    }
+
+    if (!messageColumns.Contains("ForwardedFromExternalMessageId"))
+    {
+        await db.Database.ExecuteSqlRawAsync("ALTER TABLE Messages ADD COLUMN ForwardedFromExternalMessageId TEXT;");
+    }
+
    var attachmentColumns = new HashSet<string>(StringComparer.OrdinalIgnoreCase);
    await using (var command = connection.CreateCommand())
    {
@@ -385,6 +407,22 @@ static async Task RemoveGenericMediaLabelsAsync(QMaxDbContext db)
    var attachments = await db.MessageAttachments.ToListAsync();
    foreach (var attachment in attachments)
    {
+        if (attachment.Kind == AttachmentKind.File)
+        {
+            var inferredKind = AttachmentStorageService.GuessKind(
+                attachment.ContentType,
+                Path.GetExtension(attachment.OriginalFileName));
+            if (inferredKind != AttachmentKind.File)
+            {
+                attachment.Kind = inferredKind;
+            }
+        }
+
+        attachment.ContentType = AttachmentStorageService.NormalizeContentType(
+            attachment.ContentType,
+            attachment.OriginalFileName,
+            attachment.Kind);
+
        var normalizedFileName = AttachmentStorageService.NormalizeRemoteFileName(
            attachment.OriginalFileName,
            attachment.ContentType,
@@ -409,7 +409,13 @@ public sealed class MaxBridgeSyncService(

                foreach (var incomingAttachment in DistinctAttachments(incoming.Attachments ?? []))
                {
-                    var attachment = await CreateAttachmentAsync(incomingAttachment, maxBridgeClient, storage, cancellationToken);
+                    var attachment = await CreateAttachmentAsync(
+                        db,
+                        incoming,
+                        incomingAttachment,
+                        maxBridgeClient,
+                        storage,
+                        cancellationToken);
                    if (attachment is not null)
                    {
                        message.Attachments.Add(attachment);
@@ -1024,6 +1030,35 @@ public sealed class MaxBridgeSyncService(

        foreach (var incomingAttachment in incomingAttachments)
        {
+            var existingAttachment = FindMatchingAttachment(knownAttachments, incomingAttachment);
+            if (existingAttachment is not null)
+            {
+                if (IsUncachedRemotePlaceholder(existingAttachment) &&
+                    RequiresCachedRemoteMedia(existingAttachment.Kind))
+                {
+                    var hydrated = await TryHydrateRemoteAttachmentAsync(
+                        existingAttachment,
+                        incomingAttachment,
+                        maxBridgeClient,
+                        storage,
+                        cancellationToken);
+                    if (!hydrated)
+                    {
+                        hydrated = await TryHydrateFromCachedOutgoingAsync(
+                            db,
+                            existingAttachment,
+                            incoming,
+                            incomingAttachment,
+                            storage,
+                            cancellationToken);
+                    }
+
+                    changed |= hydrated;
+                }
+
+                continue;
+            }
+
            if (TryMergeOutgoingRemoteEchoIntoLocalAttachment(
                message,
                incoming,
@@ -1035,20 +1070,13 @@ public sealed class MaxBridgeSyncService(
                continue;
            }

-            var existingAttachment = FindMatchingAttachment(knownAttachments, incomingAttachment);
-            if (existingAttachment is not null)
-            {
-                if (IsUncachedRemotePlaceholder(existingAttachment) &&
-                    RequiresCachedRemoteMedia(existingAttachment.Kind) &&
-                    await TryHydrateRemoteAttachmentAsync(existingAttachment, incomingAttachment, maxBridgeClient, storage, cancellationToken))
-                {
-                    changed = true;
-                }
-
-                continue;
-            }
-
-            var attachment = await CreateAttachmentAsync(incomingAttachment, maxBridgeClient, storage, cancellationToken);
+            var attachment = await CreateAttachmentAsync(
+                db,
+                incoming,
+                incomingAttachment,
+                maxBridgeClient,
+                storage,
+                cancellationToken);
            if (attachment is null)
            {
                continue;
@@ -1148,6 +1176,8 @@ public sealed class MaxBridgeSyncService(
    }

    private static async Task<MessageAttachment?> CreateAttachmentAsync(
+        QMaxDbContext db,
+        MaxMessageUpdate incomingMessage,
        MaxAttachmentUpdate incoming,
        IMaxBridgeClient maxBridgeClient,
        IAttachmentStorageService storage,
@@ -1221,20 +1251,62 @@ public sealed class MaxBridgeSyncService(
                // Non-visual files can stay as deferred downloads; inline media must be cached before it is shown.
            }

+            var cachedAttachment = CreateRemotePlaceholder(incoming, kind, remoteUrl);
+            if (await TryHydrateFromCachedOutgoingAsync(
+                    db,
+                    cachedAttachment,
+                    incomingMessage,
+                    incoming,
+                    storage,
+                    cancellationToken))
+            {
+                return cachedAttachment;
+            }
+
            if (RequiresCachedRemoteMedia(kind))
            {
                return null;
            }
+
+            return cachedAttachment;
        }

+        var placeholder = CreateRemotePlaceholder(incoming, kind, remoteUrl);
+        if (await TryHydrateFromCachedOutgoingAsync(
+                db,
+                placeholder,
+                incomingMessage,
+                incoming,
+                storage,
+                cancellationToken))
+        {
+            return placeholder;
+        }
+
+        return placeholder;
+    }
+
+    private static MessageAttachment CreateRemotePlaceholder(
+        MaxAttachmentUpdate incoming,
+        AttachmentKind? kind,
+        string? remoteUrl)
+    {
+        var resolvedKind = kind ?? AttachmentKind.File;
+        var originalFileName = AttachmentStorageService.NormalizeRemoteFileName(
+            incoming.FileName,
+            incoming.ContentType,
+            resolvedKind);
        return new MessageAttachment
        {
            ExternalId = incoming.ExternalId,
-            OriginalFileName = AttachmentStorageService.NormalizeRemoteFileName(incoming.FileName, incoming.ContentType, kind),
+            OriginalFileName = originalFileName,
            StorageFileName = $"remote-{Guid.NewGuid():N}",
-            ContentType = string.IsNullOrWhiteSpace(incoming.ContentType) ? "application/octet-stream" : incoming.ContentType,
+            ContentType = AttachmentStorageService.NormalizeContentType(
+                incoming.ContentType,
+                originalFileName,
+                resolvedKind),
            FileSizeBytes = incoming.FileSizeBytes ?? 0,
-            Kind = kind ?? AttachmentKind.File,
+            Kind = resolvedKind,
            SortOrder = incoming.SortOrder,
            RemoteUrl = remoteUrl
        };
@@ -1281,11 +1353,93 @@ public sealed class MaxBridgeSyncService(

    private static bool IsUncachedRemotePlaceholder(MessageAttachment attachment)
    {
-        return !string.IsNullOrWhiteSpace(attachment.RemoteUrl) &&
-            attachment.StorageFileName.StartsWith("remote-", StringComparison.Ordinal) &&
+        return attachment.StorageFileName.StartsWith("remote-", StringComparison.Ordinal) &&
            (attachment.FileSizeBytes <= 0 || string.IsNullOrWhiteSpace(attachment.Sha256));
    }

+    private static async Task<bool> TryHydrateFromCachedOutgoingAsync(
+        QMaxDbContext db,
+        MessageAttachment attachment,
+        MaxMessageUpdate incomingMessage,
+        MaxAttachmentUpdate incomingAttachment,
+        IAttachmentStorageService storage,
+        CancellationToken cancellationToken)
+    {
+        if (string.IsNullOrWhiteSpace(incomingMessage.ExternalId))
+        {
+            return false;
+        }
+
+        var kind = ResolveKind(incomingAttachment) ?? attachment.Kind;
+        var expectedSize = incomingAttachment.FileSizeBytes.GetValueOrDefault();
+        var messages = await db.Messages
+            .IgnoreQueryFilters()
+            .AsNoTracking()
+            .Include(x => x.Attachments)
+            .Where(x =>
+                x.ExternalId == incomingMessage.ExternalId &&
+                x.Direction == MessageDirection.Outgoing &&
+                x.DeletedAt == null)
+            .ToListAsync(cancellationToken);
+
+        var cached = messages
+            .SelectMany(x => x.Attachments)
+            .Where(x =>
+                x.Kind == kind &&
+                x.SortOrder == incomingAttachment.SortOrder &&
+                (string.IsNullOrWhiteSpace(incomingAttachment.ExternalId) ||
+                    x.ExternalId == incomingAttachment.ExternalId) &&
+                (expectedSize <= 0 || x.FileSizeBytes == expectedSize) &&
+                x.FileSizeBytes > 0 &&
+                !string.IsNullOrWhiteSpace(x.Sha256) &&
+                !x.StorageFileName.StartsWith("remote-", StringComparison.Ordinal))
+            .Select(x => new { Attachment = x, Path = storage.GetPath(x.StorageFileName) })
+            .FirstOrDefault(x =>
+                File.Exists(x.Path) &&
+                new FileInfo(x.Path).Length == x.Attachment.FileSizeBytes);
+        if (cached is null)
+        {
+            return false;
+        }
+
+        try
+        {
+            await using var source = new FileStream(
+                cached.Path,
+                FileMode.Open,
+                FileAccess.Read,
+                FileShare.Read,
+                128 * 1024,
+                useAsync: true);
+            var stored = await storage.SaveRemoteAsync(
+                incomingAttachment.FileName,
+                cached.Attachment.ContentType,
+                source,
+                expectedSize > 0 ? expectedSize : cached.Attachment.FileSizeBytes,
+                kind,
+                cancellationToken);
+
+            attachment.ExternalId = string.IsNullOrWhiteSpace(incomingAttachment.ExternalId)
+                ? attachment.ExternalId
+                : incomingAttachment.ExternalId;
+            attachment.OriginalFileName = stored.OriginalFileName;
+            attachment.StorageFileName = stored.StorageFileName;
+            attachment.ContentType = stored.ContentType;
+            attachment.FileSizeBytes = stored.FileSizeBytes;
+            attachment.Sha256 = stored.Sha256;
+            attachment.Kind = stored.Kind;
+            attachment.SortOrder = incomingAttachment.SortOrder;
+            attachment.RemoteUrl = string.IsNullOrWhiteSpace(incomingAttachment.RemoteUrl)
+                ? attachment.RemoteUrl
+                : incomingAttachment.RemoteUrl;
+            return true;
+        }
+        catch (IOException)
+        {
+            return false;
+        }
+    }
+
    private static async Task<bool> TryHydrateRemoteAttachmentAsync(
        MessageAttachment attachment,
        MaxAttachmentUpdate incoming,
@@ -1342,7 +1496,15 @@ public sealed class MaxBridgeSyncService(
        if (!string.IsNullOrWhiteSpace(attachment.Kind) &&
            Enum.TryParse<AttachmentKind>(attachment.Kind, ignoreCase: true, out var parsed))
        {
-            return parsed;
+            if (parsed != AttachmentKind.File)
+            {
+                return parsed;
+            }
+
+            var inferred = AttachmentStorageService.GuessKind(
+                attachment.ContentType,
+                Path.GetExtension(attachment.FileName));
+            return inferred == AttachmentKind.File ? parsed : inferred;
        }

        var extension = Path.GetExtension(attachment.FileName);
@@ -278,6 +278,16 @@ public sealed class MaxOutboxService(
    {
        var externalChatId = chat.ExternalId!;
        var chatUrl = chat.WebUrl;
+        if (!string.IsNullOrWhiteSpace(message.ForwardedFromExternalChatId) &&
+            !string.IsNullOrWhiteSpace(message.ForwardedFromExternalMessageId))
+        {
+            return await maxBridge.ForwardMessageAsync(
+                externalChatId,
+                message.ForwardedFromExternalChatId,
+                message.ForwardedFromExternalMessageId,
+                cancellationToken);
+        }
+
        var attachments = message.Attachments.OrderBy(attachment => attachment.SortOrder).ToArray();
        if (attachments.Length == 0)
        {
@@ -46,7 +46,9 @@ public static class MessageTextSanitizer
            "\u0430\u0443\u0434\u0438\u043e" => true,
            "audio" => true,
            "\u0433\u043e\u043b\u043e\u0441\u043e\u0432\u043e\u0435" => true,
+            "\u0433\u043e\u043b\u043e\u0441\u043e\u0432\u043e\u0435 \u0441\u043e\u043e\u0431\u0449\u0435\u043d\u0438\u0435" => true,
            "voice" => true,
+            "voice message" => true,
            "\u0441\u0442\u0438\u043a\u0435\u0440" => true,
            "sticker" => true,
            "\u044d\u043c\u043e\u0434\u0437\u0438" => true,
@@ -365,7 +365,7 @@ public sealed class ApiSmokeTests : IDisposable

        var stored = await storage.SaveRemoteAsync(
            "voice.m4a",
-            "audio/mp4",
+            "application/octet-stream",
            stream,
            bytes.Length,
            null,
@@ -376,6 +376,7 @@ public sealed class ApiSmokeTests : IDisposable
        Assert.False(File.Exists(finalPath + ".part"));
        Assert.Equal(bytes.Length, stored.FileSizeBytes);
        Assert.Equal(AttachmentKind.VoiceNote, stored.Kind);
+        Assert.Equal("audio/mp4", stored.ContentType);
        Assert.Equal(bytes, await File.ReadAllBytesAsync(finalPath));

        Directory.Delete(storagePath, recursive: true);
@@ -479,6 +480,194 @@ public sealed class ApiSmokeTests : IDisposable
        Assert.Equal(bridge.RemoteUrl, storedAttachment.RemoteUrl);
    }

+    [Fact]
+    public async Task SyncMergesGenericFileEchoIntoOutgoingVoiceNote()
+    {
+        var voiceBytes = new byte[] { 0x00, 0x00, 0x00, 0x18, 0x66, 0x74, 0x79, 0x70, 0x4D, 0x34, 0x41, 0x20 };
+        var bridge = new OutgoingAttachmentEchoMaxBridgeClient(
+            AttachmentKind.File,
+            "remote-voice.m4a",
+            "application/octet-stream",
+            voiceBytes);
+        using var factory = _factory.WithWebHostBuilder(builder =>
+        {
+            builder.ConfigureTestServices(services =>
+            {
+                services.RemoveAll<IHostedService>();
+                services.RemoveAll<IMaxBridgeClient>();
+                services.AddSingleton<IMaxBridgeClient>(bridge);
+            });
+        });
+        using var client = factory.CreateClient();
+        await LoginAsync(client);
+
+        var chat = await CreateDirectChatAsync(client, bridge.ChatExternalId, "Outgoing Voice Echo");
+        using var form = new MultipartFormDataContent();
+        using var fileContent = new ByteArrayContent(voiceBytes);
+        fileContent.Headers.ContentType = new MediaTypeHeaderValue("audio/mp4");
+        form.Add(fileContent, "file", "local-voice.m4a");
+
+        var upload = await client.PostAsync($"/api/chats/{chat.Id}/attachments", form);
+        await AssertStatusAsync(HttpStatusCode.OK, upload);
+        var sent = await upload.Content.ReadFromJsonAsync<MessageDto>(JsonOptions);
+        Assert.NotNull(sent);
+
+        Assert.True(await ProcessOutboxAsync(factory) >= 1);
+        var sync = await client.PostAsync("/api/max/sync", null);
+        await AssertStatusAsync(HttpStatusCode.OK, sync);
+
+        var messages = await client.GetFromJsonAsync<MessageDto[]>($"/api/chats/{chat.Id}/messages", JsonOptions);
+        var echoed = Assert.Single(messages!);
+        Assert.Equal(sent!.Id, echoed.Id);
+        var attachment = Assert.Single(echoed.Attachments);
+        Assert.Equal(AttachmentKind.VoiceNote, attachment.Kind);
+        Assert.Equal("audio/mp4", attachment.ContentType);
+        Assert.Equal(voiceBytes.Length, attachment.FileSizeBytes);
+    }
+
+    [Fact]
+    public async Task SyncHydratesIncomingVoiceWithoutRemoteUrlFromMatchingOutgoingCache()
+    {
+        var voiceBytes = new byte[] { 0x00, 0x00, 0x00, 0x18, 0x66, 0x74, 0x79, 0x70, 0x4D, 0x34, 0x41, 0x20 };
+        var bridge = new OutgoingAttachmentEchoMaxBridgeClient(
+            AttachmentKind.File,
+            "received-voice.m4a",
+            "application/octet-stream",
+            voiceBytes,
+            isOutgoing: false,
+            includeRemoteUrl: false,
+            allowMediaDownload: false);
+        using var factory = _factory.WithWebHostBuilder(builder =>
+        {
+            builder.ConfigureTestServices(services =>
+            {
+                services.RemoveAll<IHostedService>();
+                services.RemoveAll<IMaxBridgeClient>();
+                services.AddSingleton<IMaxBridgeClient>(bridge);
+            });
+        });
+        using var client = factory.CreateClient();
+        await LoginAsync(client);
+
+        var target = await CreateDirectChatAsync(client, bridge.ChatExternalId, "Incoming Voice");
+        var firstSync = await client.PostAsync("/api/max/sync", null);
+        await AssertStatusAsync(HttpStatusCode.OK, firstSync);
+
+        await using (var scope = factory.Services.CreateAsyncScope())
+        {
+            var db = scope.ServiceProvider.GetRequiredService<QMaxDbContext>();
+            var placeholder = await db.MessageAttachments
+                .SingleAsync(x => x.ExternalId == bridge.RemoteAttachmentExternalId);
+            Assert.StartsWith("remote-", placeholder.StorageFileName);
+            Assert.Null(placeholder.Sha256);
+        }
+
+        var source = await CreateDirectChatAsync(client, $"voice-source-{Guid.NewGuid():N}", "Voice Source");
+        using var form = new MultipartFormDataContent();
+        using var fileContent = new ByteArrayContent(voiceBytes);
+        fileContent.Headers.ContentType = new MediaTypeHeaderValue("audio/mp4");
+        form.Add(fileContent, "file", "sent-voice.m4a");
+        var upload = await client.PostAsync($"/api/chats/{source.Id}/attachments", form);
+        await AssertStatusAsync(HttpStatusCode.OK, upload);
+        var sourceMessage = await upload.Content.ReadFromJsonAsync<MessageDto>(JsonOptions);
+        Assert.NotNull(sourceMessage);
+
+        await using (var scope = factory.Services.CreateAsyncScope())
+        {
+            var db = scope.ServiceProvider.GetRequiredService<QMaxDbContext>();
+            var storedSource = await db.Messages
+                .Include(x => x.Attachments)
+                .SingleAsync(x => x.Id == sourceMessage!.Id);
+            storedSource.ExternalId = bridge.MessageExternalId;
+            storedSource.DeliveryState = MessageDeliveryState.Sent;
+            Assert.Single(storedSource.Attachments).ExternalId = bridge.RemoteAttachmentExternalId;
+            await db.SaveChangesAsync();
+        }
+
+        var secondSync = await client.PostAsync("/api/max/sync", null);
+        await AssertStatusAsync(HttpStatusCode.OK, secondSync);
+
+        var messages = await client.GetFromJsonAsync<MessageDto[]>($"/api/chats/{target.Id}/messages", JsonOptions);
+        var received = Assert.Single(messages!);
+        Assert.Equal(MessageDirection.Incoming, received.Direction);
+        var attachment = Assert.Single(received.Attachments);
+        Assert.Equal(AttachmentKind.VoiceNote, attachment.Kind);
+        Assert.Equal("audio/mp4", attachment.ContentType);
+        Assert.Equal(voiceBytes.Length, attachment.FileSizeBytes);
+
+        var download = await client.GetAsync(attachment.DownloadPath);
+        await AssertStatusAsync(HttpStatusCode.OK, download);
+        Assert.Equal(voiceBytes, await download.Content.ReadAsByteArrayAsync());
+    }
+
+    [Fact]
+    public async Task ForwardedVoiceUsesNativeForwardAndDoesNotDuplicateOnEcho()
+    {
+        var voiceBytes = new byte[] { 0x4F, 0x67, 0x67, 0x53, 0x00, 0x02, 0x56, 0x4F, 0x49, 0x43, 0x45 };
+        var bridge = new OutgoingAttachmentEchoMaxBridgeClient(
+            AttachmentKind.VoiceNote,
+            "max-voice.ogg",
+            "audio/ogg",
+            voiceBytes);
+        using var factory = _factory.WithWebHostBuilder(builder =>
+        {
+            builder.ConfigureTestServices(services =>
+            {
+                services.RemoveAll<IHostedService>();
+                services.RemoveAll<IMaxBridgeClient>();
+                services.AddSingleton<IMaxBridgeClient>(bridge);
+            });
+        });
+        using var client = factory.CreateClient();
+        await LoginAsync(client);
+
+        var source = await CreateDirectChatAsync(client, $"voice-source-{Guid.NewGuid():N}", "Voice Source");
+        var target = await CreateDirectChatAsync(client, bridge.ChatExternalId, "Voice Target");
+        using var form = new MultipartFormDataContent();
+        using var fileContent = new ByteArrayContent(voiceBytes);
+        fileContent.Headers.ContentType = new MediaTypeHeaderValue("audio/ogg");
+        form.Add(fileContent, "file", "source-voice.ogg");
+
+        var upload = await client.PostAsync($"/api/chats/{source.Id}/attachments", form);
+        await AssertStatusAsync(HttpStatusCode.OK, upload);
+        var sourceMessage = await upload.Content.ReadFromJsonAsync<MessageDto>(JsonOptions);
+        Assert.NotNull(sourceMessage);
+
+        await using (var scope = factory.Services.CreateAsyncScope())
+        {
+            var db = scope.ServiceProvider.GetRequiredService<QMaxDbContext>();
+            var storedSource = await db.Messages.SingleAsync(x => x.Id == sourceMessage!.Id);
+            storedSource.ExternalId = $"source-voice-{Guid.NewGuid():N}";
+            storedSource.DeliveryState = MessageDeliveryState.Sent;
+            await db.SaveChangesAsync();
+        }
+
+        var forwardResponse = await client.PostAsJsonAsync(
+            $"/api/chats/{source.Id}/messages/{sourceMessage!.Id}/forward",
+            new ForwardMessageRequest(target.Id));
+        await AssertStatusAsync(HttpStatusCode.OK, forwardResponse);
+        var pendingForward = await forwardResponse.Content.ReadFromJsonAsync<MessageDto>(JsonOptions);
+        Assert.NotNull(pendingForward);
+        Assert.Equal(MessageDeliveryState.Sending, pendingForward!.DeliveryState);
+        Assert.Equal(AttachmentKind.VoiceNote, Assert.Single(pendingForward.Attachments).Kind);
+
+        Assert.True(await ProcessOutboxAsync(factory) >= 1);
+        var sync = await client.PostAsync("/api/max/sync", null);
+        await AssertStatusAsync(HttpStatusCode.OK, sync);
+
+        var targetMessages = await client.GetFromJsonAsync<MessageDto[]>($"/api/chats/{target.Id}/messages", JsonOptions);
+        var forwarded = Assert.Single(targetMessages!);
+        Assert.Equal(pendingForward.Id, forwarded.Id);
+        Assert.Equal(bridge.MessageExternalId, forwarded.ExternalId);
+        Assert.Equal(MessageDeliveryState.Sent, forwarded.DeliveryState);
+        var attachment = Assert.Single(forwarded.Attachments);
+        Assert.Equal(AttachmentKind.VoiceNote, attachment.Kind);
+
+        var download = await client.GetAsync(attachment.DownloadPath);
+        await AssertStatusAsync(HttpStatusCode.OK, download);
+        Assert.Equal(voiceBytes, await download.Content.ReadAsByteArrayAsync());
+    }
+
    [Fact]
    public async Task ForwardMessageFlowCopiesTextAndAttachments()
    {
@@ -1771,6 +1960,8 @@ public sealed class ApiSmokeTests : IDisposable
            .Options;
        var messageId = Guid.NewGuid();
        var localAttachmentId = Guid.NewGuid();
+        var voiceMessageId = Guid.NewGuid();
+        var localVoiceAttachmentId = Guid.NewGuid();

        try
        {
@@ -1810,7 +2001,38 @@ public sealed class ApiSmokeTests : IDisposable
                    Kind = AttachmentKind.Image,
                    SortOrder = 0
                });
-                db.Messages.Add(message);
+                var voiceMessage = new Message
+                {
+                    Id = voiceMessageId,
+                    Chat = chat,
+                    ExternalId = "domhist:voice",
+                    Direction = MessageDirection.Outgoing,
+                    DeliveryState = MessageDeliveryState.Sent,
+                    SentAt = DateTimeOffset.UtcNow.AddSeconds(1)
+                };
+                voiceMessage.Attachments.Add(new MessageAttachment
+                {
+                    Id = localVoiceAttachmentId,
+                    OriginalFileName = "local-voice.m4a",
+                    StorageFileName = $"{Guid.NewGuid():N}.m4a",
+                    ContentType = "audio/mp4",
+                    FileSizeBytes = 35_985,
+                    Sha256 = "same-voice-sha",
+                    Kind = AttachmentKind.VoiceNote,
+                    SortOrder = 0
+                });
+                voiceMessage.Attachments.Add(new MessageAttachment
+                {
+                    OriginalFileName = "remote-voice.m4a",
+                    StorageFileName = $"{Guid.NewGuid():N}.m4a",
+                    ExternalId = "dommedia:voice",
+                    ContentType = "application/octet-stream",
+                    FileSizeBytes = 35_985,
+                    Sha256 = "",
+                    Kind = AttachmentKind.File,
+                    SortOrder = 0
+                });
+                db.Messages.AddRange(message, voiceMessage);
                await db.SaveChangesAsync();
            }

@@ -1825,6 +2047,12 @@ public sealed class ApiSmokeTests : IDisposable
            Assert.Equal("local-photo.png", attachment.OriginalFileName);
            Assert.Equal("dommedia:remote", attachment.ExternalId);
            Assert.Equal("https://max.test/media/photo.jpg", attachment.RemoteUrl);
+
+            var voiceAttachment = await verifyDb.MessageAttachments.SingleAsync(x => x.MessageId == voiceMessageId);
+            Assert.Equal(localVoiceAttachmentId, voiceAttachment.Id);
+            Assert.Equal(AttachmentKind.VoiceNote, voiceAttachment.Kind);
+            Assert.Equal("audio/mp4", voiceAttachment.ContentType);
+            Assert.Equal("dommedia:voice", voiceAttachment.ExternalId);
        }
        finally
        {
@@ -2509,10 +2737,35 @@ public sealed class ApiSmokeTests : IDisposable
    private sealed class OutgoingAttachmentEchoMaxBridgeClient : IMaxBridgeClient
    {
        public readonly string ChatExternalId = $"mock-outgoing-attachment-echo-{Guid.NewGuid():N}";
-        public readonly string MessageExternalId = $"outgoing-photo-{Guid.NewGuid():N}";
+        public readonly string MessageExternalId = $"outgoing-media-{Guid.NewGuid():N}";
        public readonly string RemoteAttachmentExternalId = $"dommedia:{Guid.NewGuid():N}";
-        public readonly string RemoteUrl = $"https://max.test/media/{Guid.NewGuid():N}.jpg";
-        private static readonly byte[] RemoteBytes = [0xFF, 0xD8, 0x52, 0x45, 0x4D, 0x4F, 0x54, 0x45, 0xFF, 0xD9];
+        public readonly string? RemoteUrl;
+        private readonly AttachmentKind _kind;
+        private readonly string _fileName;
+        private readonly string _contentType;
+        private readonly byte[] _remoteBytes;
+        private readonly bool _isOutgoing;
+        private readonly bool _allowMediaDownload;
+
+        public OutgoingAttachmentEchoMaxBridgeClient(
+            AttachmentKind kind = AttachmentKind.Image,
+            string fileName = "max-image-1.jpg",
+            string contentType = "image/jpeg",
+            byte[]? remoteBytes = null,
+            bool isOutgoing = true,
+            bool includeRemoteUrl = true,
+            bool allowMediaDownload = true)
+        {
+            _kind = kind;
+            _fileName = fileName;
+            _contentType = contentType;
+            _remoteBytes = remoteBytes ?? [0xFF, 0xD8, 0x52, 0x45, 0x4D, 0x4F, 0x54, 0x45, 0xFF, 0xD9];
+            _isOutgoing = isOutgoing;
+            _allowMediaDownload = allowMediaDownload;
+            RemoteUrl = includeRemoteUrl
+                ? $"https://max.test/media/{Guid.NewGuid():N}{Path.GetExtension(fileName)}"
+                : null;
+        }

        public Task<MaxBridgeStatus> GetStatusAsync(CancellationToken cancellationToken)
        {
@@ -2549,17 +2802,17 @@ public sealed class ApiSmokeTests : IDisposable
                            MessageExternalId,
                            "self",
                            "You",
-                            true,
+                            _isOutgoing,
                            "",
                            sentAt,
                            [
                                new MaxAttachmentUpdate(
                                    RemoteAttachmentExternalId,
-                                    "max-image-1.jpg",
-                                    "image/jpeg",
-                                    RemoteBytes.Length,
+                                    _fileName,
+                                    _contentType,
+                                    _remoteBytes.Length,
                                    RemoteUrl,
-                                    nameof(AttachmentKind.Image),
+                                    _kind.ToString(),
                                    0)
                            ])
                    ],
@@ -2604,6 +2857,15 @@ public sealed class ApiSmokeTests : IDisposable
            return Task.FromResult(new MaxSendResult(true, MessageExternalId, null));
        }

+        public Task<MaxSendResult> ForwardMessageAsync(
+            string externalChatId,
+            string sourceExternalChatId,
+            string sourceExternalMessageId,
+            CancellationToken cancellationToken)
+        {
+            return Task.FromResult(new MaxSendResult(true, MessageExternalId, null));
+        }
+
        public Task<MaxActionResult> EditMessageAsync(string externalChatId, string externalMessageId, string? currentText, string text, CancellationToken cancellationToken)
        {
            return Task.FromResult(new MaxActionResult(true, null));
@@ -2626,8 +2888,13 @@ public sealed class ApiSmokeTests : IDisposable

        public Task<MaxMediaDownload?> DownloadMediaAsync(string remoteUrl, CancellationToken cancellationToken)
        {
+            if (!_allowMediaDownload)
+            {
+                return Task.FromResult<MaxMediaDownload?>(null);
+            }
+
            return Task.FromResult<MaxMediaDownload?>(
-                new MaxMediaDownload(new MemoryStream(RemoteBytes), "image/jpeg", RemoteBytes.Length));
+                new MaxMediaDownload(new MemoryStream(_remoteBytes), _contentType, _remoteBytes.Length));
        }
    }