Merge pull request #173 from Sea-Haven-Industries/fix/ab/sh-383-media-contract

fix(media): lift the 1 MB proxy body cap and apply the SH-116 media contract

.platform/nginx/conf.d/01_upload_body_size.conf

@@ -0,0 +1,6 @@
+# The Elastic Beanstalk nginx proxy defaults client_max_body_size to 1m,
+# which returned 413 for every media upload over ~1 MB before the request reached
+# the API. The cap sits above the API's own request limit
+# (WorkOrderMediaContract.MaxUploadRequestBytes = 110 MB) so oversize uploads get
+# the API's generic per-kind message instead of an nginx error page.
+client_max_body_size 120M;

Api.SeaHavenIndustries.Tests/VendorPortalDocumentTests.cs

@@ -54,6 +54,11 @@ public sealed class VendorPortalDocumentTests : IDisposable
         var upliftData = new Mock<IUpliftDataService>();
         upliftData.Setup(u => u.GetForVendorDispatchAsync(It.IsAny<int>(), It.IsAny<CancellationToken>()))
             .ReturnsAsync(new List<PortalUpliftData>());
+        upliftData.Setup(u => u.ExecuteWorkOrderMutationAsync(
+                It.IsAny<int>(),
+                It.IsAny<Func<CancellationToken, Task<VendorCompletionDocument>>>(),
+                It.IsAny<CancellationToken>()))
+            .Returns((int _, Func<CancellationToken, Task<VendorCompletionDocument>> work, CancellationToken ct) => work(ct));
         var commentData = new Mock<ICommentDataService>();
         commentData.Setup(c => c.GetVendorViewableForDispatchAsync(It.IsAny<int>(), It.IsAny<CancellationToken>()))
             .ReturnsAsync(new List<PortalCommentData>());
@@ -363,6 +368,278 @@ public sealed class VendorPortalDocumentTests : IDisposable
         context.VendorCompletionDocuments.Should().HaveCount(1);
     }
 
+    [Fact]
+    public void UploadCompletionDocument_AdvertisesContractRequestLimit()
+    {
+        var attribute = Assert.Single(
+            typeof(VendorPortalController)
+                .GetMethod(nameof(VendorPortalController.UploadCompletionDocument))!
+                .CustomAttributes,
+            candidate => candidate.AttributeType == typeof(RequestSizeLimitAttribute));
+        var bytes = Assert.Single(attribute.ConstructorArguments);
+
+        bytes.Value.Should().Be(110_000_000L);
+    }
+
+    private static byte[] MediaBytes(int size, params byte[] header)
+    {
+        var bytes = new byte[size];
+        header.AsSpan().CopyTo(bytes);
+        return bytes;
+    }
+
+    private static byte[] FtypVideoBytes(int size) => MediaBytes(
+        size, 0x00, 0x00, 0x00, 0x20, (byte)'f', (byte)'t', (byte)'y', (byte)'p',
+        (byte)'i', (byte)'s', (byte)'o', (byte)'m');
+
+    [Fact]
+    public async Task UploadCompletionDocument_AcceptsSixtyMegabyteVideo()
+    {
+        using var context = NewContext();
+        var (_, dispatch) = await SeedDispatch(context);
+
+        var result = await NewController(context).UploadCompletionDocument(
+            dispatch.Id,
+            FormFile(FtypVideoBytes(60_000_000), "site-clip.mp4", "video/mp4"));
+
+        result.Should().BeOfType<OkObjectResult>();
+        var document = await context.VendorCompletionDocuments.SingleAsync();
+        document.ContentType.Should().Be("video/mp4");
+        document.SizeBytes.Should().Be(60_000_000L);
+    }
+
+    [Fact]
+    public async Task UploadCompletionDocument_AcceptsMovWithEmptyContentType()
+    {
+        using var context = NewContext();
+        var (_, dispatch) = await SeedDispatch(context);
+
+        var result = await NewController(context).UploadCompletionDocument(
+            dispatch.Id,
+            FormFile(FtypVideoBytes(2_048), "site-clip.MOV", ""));
+
+        result.Should().BeOfType<OkObjectResult>();
+        (await context.VendorCompletionDocuments.SingleAsync()).ContentType.Should().Be("video/quicktime");
+    }
+
+    [Fact]
+    public async Task UploadCompletionDocument_AcceptsIosTranscodedJpegLabelledHeic()
+    {
+        using var context = NewContext();
+        var (_, dispatch) = await SeedDispatch(context);
+
+        var result = await NewController(context).UploadCompletionDocument(
+            dispatch.Id,
+            FormFile(MediaBytes(4_096, 0xFF, 0xD8, 0xFF, 0xE0), "IMG_2044.jpg", "image/heic"));
+
+        result.Should().BeOfType<OkObjectResult>();
+        (await context.VendorCompletionDocuments.SingleAsync()).ContentType.Should().Be("image/jpeg");
+    }
+
+    [Theory]
+    // Genuine PDF/JPEG bytes and declared type, but a video file name: the size class must
+    // follow the validated type, not the name, or the document/photo caps are bypassed.
+    [InlineData("report.mp4", "application/pdf", 12_000_000, new byte[] { 0x25, 0x50, 0x44, 0x46, 0x2D })]
+    [InlineData("site.mov", "image/jpeg", 11_000_000, new byte[] { 0xFF, 0xD8, 0xFF, 0xE0 })]
+    public async Task UploadCompletionDocument_VideoExtensionDoesNotWidenSizeCap(
+        string fileName,
+        string contentType,
+        int size,
+        byte[] header)
+    {
+        using var context = NewContext();
+        var (_, dispatch) = await SeedDispatch(context);
+
+        var result = await NewController(context).UploadCompletionDocument(
+            dispatch.Id,
+            FormFile(MediaBytes(size, header), fileName, contentType));
+
+        result.Should().BeOfType<BadRequestObjectResult>();
+        context.VendorCompletionDocuments.Should().BeEmpty();
+    }
+
+    /// <summary>ftyp + mdat + moov/mvhd (moov last, as phones write it).</summary>
+    private static byte[] PhoneVideoBytes(uint durationSeconds)
+    {
+        static byte[] Box(string type, byte[] body)
+        {
+            var box = new byte[8 + body.Length];
+            System.Buffers.Binary.BinaryPrimitives.WriteUInt32BigEndian(box, (uint)box.Length);
+            System.Text.Encoding.ASCII.GetBytes(type).CopyTo(box, 4);
+            body.CopyTo(box, 8);
+            return box;
+        }
+
+        var mvhd = new byte[20];
+        System.Buffers.Binary.BinaryPrimitives.WriteUInt32BigEndian(mvhd.AsSpan(12), 600);
+        System.Buffers.Binary.BinaryPrimitives.WriteUInt32BigEndian(mvhd.AsSpan(16), durationSeconds * 600);
+        return Box("ftyp", System.Text.Encoding.ASCII.GetBytes("qt  \0\0\0\0"))
+            .Concat(Box("mdat", new byte[4096]))
+            .Concat(Box("moov", Box("mvhd", mvhd)))
+            .ToArray();
+    }
+
+    [Theory]
+    [InlineData(95u, false)]
+    [InlineData(89u, true)]
+    public async Task UploadCompletionDocument_EnforcesNinetySecondVideoLimit(uint seconds, bool accepted)
+    {
+        using var context = NewContext();
+        var (_, dispatch) = await SeedDispatch(context);
+
+        var result = await NewController(context).UploadCompletionDocument(
+            dispatch.Id,
+            FormFile(PhoneVideoBytes(seconds), "IMG_0042.MOV", "video/quicktime"));
+
+        if (accepted)
+        {
+            result.Should().BeOfType<OkObjectResult>();
+        }
+        else
+        {
+            result.Should().BeOfType<BadRequestObjectResult>();
+            context.VendorCompletionDocuments.Should().BeEmpty();
+        }
+    }
+
+    [Fact]
+    public async Task UploadCompletionDocument_RejectsFourthVideoAcrossDispatcherAndVendorUploads()
+    {
+        using var context = NewContext();
+        var (_, dispatch) = await SeedDispatch(context);
+        foreach (var name in new[] { "IMG_0001.MOV", "IMG_0002.MOV", "clip.mp4" })
+        {
+            context.workOrderAttachments.Add(new WorkOrderAttachments
+            {
+                WorkorderId = dispatch.WorkOrderId!.Value,
+                Attachments = $"https://api.example.com/Assets/Documents/{Guid.NewGuid()}_{name}",
+            });
+        }
+        await context.SaveChangesAsync();
+
+        var result = await NewController(context).UploadCompletionDocument(
+            dispatch.Id,
+            FormFile(FtypVideoBytes(2_048), "site-clip.MOV", "video/quicktime"));
+
+        result.Should().BeOfType<BadRequestObjectResult>();
+        context.VendorCompletionDocuments.Should().BeEmpty();
+    }
+
+    [Fact]
+    public async Task UploadCompletionDocument_NewVersionDoesNotCountTheVideoItReplaces()
+    {
+        using var context = NewContext();
+        var (vendor, dispatch) = await SeedDispatch(context);
+        foreach (var name in new[] { "IMG_0001.MOV", "IMG_0002.MOV" })
+        {
+            context.workOrderAttachments.Add(new WorkOrderAttachments
+            {
+                WorkorderId = dispatch.WorkOrderId!.Value,
+                Attachments = $"https://api.example.com/Assets/Documents/{Guid.NewGuid()}_{name}",
+            });
+        }
+        context.VendorCompletionDocuments.Add(new VendorCompletionDocument
+        {
+            VendorId = vendor.Id,
+            DispatchId = dispatch.Id,
+            WorkOrderId = dispatch.WorkOrderId!.Value,
+            ContentType = "video/mp4",
+            StoredFileName = "v1.mp4",
+            Version = 1,
+            Purpose = "Completion"
+        });
+        await context.SaveChangesAsync();
+
+        var result = await NewController(context).UploadCompletionDocument(
+            dispatch.Id,
+            FormFile(FtypVideoBytes(2_048), "site-clip-v2.mp4", "video/mp4"));
+
+        result.Should().BeOfType<OkObjectResult>();
+        context.VendorCompletionDocuments.Should().HaveCount(2);
+    }
+
+    [Fact]
+    public async Task GetDispatchDetail_ReportsWorkOrderMediaCountsForThePortalPreCheck()
+    {
+        using var context = NewContext();
+        var (vendor, dispatch) = await SeedDispatch(context);
+        foreach (var name in new[] { "IMG_0001.MOV", "IMG_0002.MOV", "IMG_0003.jpg" })
+        {
+            context.workOrderAttachments.Add(new WorkOrderAttachments
+            {
+                WorkorderId = dispatch.WorkOrderId!.Value,
+                Attachments = $"https://api.example.com/Assets/Documents/{Guid.NewGuid()}_{name}",
+            });
+        }
+        context.VendorCompletionDocuments.Add(new VendorCompletionDocument
+        {
+            VendorId = vendor.Id,
+            DispatchId = dispatch.Id,
+            WorkOrderId = dispatch.WorkOrderId!.Value,
+            ContentType = "video/mp4",
+            StoredFileName = "v1.mp4",
+            Version = 1,
+            Purpose = "Completion"
+        });
+        await context.SaveChangesAsync();
+
+        var service = NewService(context);
+        var session = await service.ResolveSessionAsync(Token, CancellationToken.None);
+        var detail = await service.GetDispatchDetailAsync(session!, dispatch.Id, CancellationToken.None);
+
+        detail!.MediaCounts.Should().BeEquivalentTo(new SeaHaven.Services.DTOs.PortalMediaCountsDTO
+        {
+            MaxPhotos = 10,
+            MaxVideos = 3,
+            Photos = 1,
+            Videos = 3,
+            CompletionPhotos = 1,
+            CompletionVideos = 2,
+        });
+    }
+
+    [Fact]
+    public async Task UploadCompletionDocument_RejectsVideoOverHundredMegabytes()
+    {
+        using var context = NewContext();
+        var (_, dispatch) = await SeedDispatch(context);
+
+        var result = await NewController(context).UploadCompletionDocument(
+            dispatch.Id,
+            FormFile(FtypVideoBytes(100_000_001), "site-clip.mp4", "video/mp4"));
+
+        result.Should().BeOfType<BadRequestObjectResult>();
+        context.VendorCompletionDocuments.Should().BeEmpty();
+    }
+
+    [Fact]
+    public async Task UploadCompletionDocument_RejectsPhotoOverTenMegabytes()
+    {
+        using var context = NewContext();
+        var (_, dispatch) = await SeedDispatch(context);
+
+        var result = await NewController(context).UploadCompletionDocument(
+            dispatch.Id,
+            FormFile(MediaBytes(10_000_001, 0xFF, 0xD8, 0xFF, 0xE0), "photo.jpg", "image/jpeg"));
+
+        result.Should().BeOfType<BadRequestObjectResult>();
+        context.VendorCompletionDocuments.Should().BeEmpty();
+    }
+
+    [Fact]
+    public async Task UploadCompletionDocument_RejectsUnsupportedVideoContainer()
+    {
+        using var context = NewContext();
+        var (_, dispatch) = await SeedDispatch(context);
+
+        var result = await NewController(context).UploadCompletionDocument(
+            dispatch.Id,
+            FormFile("not a video at all"u8.ToArray(), "clip.mp4", "video/mp4"));
+
+        result.Should().BeOfType<BadRequestObjectResult>();
+        context.VendorCompletionDocuments.Should().BeEmpty();
+    }
+
     [Fact]
     public async Task GetDispatchDetail_ReturnsUploadedDocumentWithQuarantineAndReplacementMetadata()
     {

Api.SeaHavenIndustries.Tests/WorkOrderMediaControllerTests.cs

@@ -1,5 +1,6 @@
 using Api.SeaHavenIndustries.Controllers;
 using Data.SeaHavenIndustries;
+using Data.SeaHavenIndustries.Enums;
 using Microsoft.AspNetCore.Http;
 using Microsoft.AspNetCore.Mvc;
 using Moq;
@@ -31,7 +32,7 @@ public class WorkOrderMediaControllerTests
     }
 
     [Fact]
-    public void AddMedia_HasTwoHundredMegabyteRequestLimit()
+    public void AddMedia_HasContractRequestLimit()
     {
         var method = typeof(WorkOrderMediaController).GetMethod(nameof(WorkOrderMediaController.AddMedia));
         var attribute = Assert.Single(
@@ -39,36 +40,293 @@ public class WorkOrderMediaControllerTests
             candidate => candidate.AttributeType == typeof(RequestSizeLimitAttribute));
         var bytes = Assert.Single(attribute.ConstructorArguments);
 
-        Assert.Equal(200_000_000L, bytes.Value);
+        Assert.Equal(110_000_000L, bytes.Value);
     }
 
     [Fact]
-    public void AddMedia_HasTwoHundredMegabyteMultipartBodyLimit()
+    public void AddMedia_HasContractMultipartBodyLimit()
     {
         var method = typeof(WorkOrderMediaController).GetMethod(nameof(WorkOrderMediaController.AddMedia));
         var attribute = Assert.IsType<RequestFormLimitsAttribute>(Assert.Single(
             method!.GetCustomAttributes(typeof(RequestFormLimitsAttribute), inherit: true)));
 
-        Assert.Equal(200_000_000L, attribute.MultipartBodyLengthLimit);
+        Assert.Equal(110_000_000L, attribute.MultipartBodyLengthLimit);
     }
 
     [Fact]
-    public async Task AddMedia_FileOverLimit_ReturnsStableUnprocessableEntity()
+    public async Task AddMedia_VideoOverHundredMegabytes_ReturnsStableUnprocessableEntity()
     {
-        var file = new Mock<IFormFile>();
-        file.SetupGet(candidate => candidate.Length).Returns(200_000_001);
+        var file = OversizeFile(100_000_001, "clip.mp4", "video/mp4", FtypHeader);
         var storage = new Mock<IFileStoragePort>(MockBehavior.Strict);
         var controller = CreateController(storage: storage);
 
-        var result = await controller.AddMedia(1, null, file.Object, CancellationToken.None);
+        var result = await controller.AddMedia(1, null, file, CancellationToken.None);
 
         var response = Assert.IsType<UnprocessableEntityObjectResult>(result);
         var error = Assert.IsType<WorkOrderBoardValidationErrorDto>(response.Value);
         Assert.Equal("FileTooLarge", error.Code);
-        Assert.Equal("The uploaded file must not exceed 200 MB.", error.Message);
+        Assert.Equal("Videos must be 100 MB or smaller.", error.Message);
         storage.VerifyNoOtherCalls();
     }
 
+    [Fact]
+    public async Task AddMedia_PhotoOverTenMegabytes_ReturnsStableUnprocessableEntity()
+    {
+        var file = OversizeFile(10_000_001, "photo.jpg", "image/jpeg", JpegHeader);
+        var storage = new Mock<IFileStoragePort>(MockBehavior.Strict);
+        var controller = CreateController(storage: storage);
+
+        var result = await controller.AddMedia(1, null, file, CancellationToken.None);
+
+        var response = Assert.IsType<UnprocessableEntityObjectResult>(result);
+        var error = Assert.IsType<WorkOrderBoardValidationErrorDto>(response.Value);
+        Assert.Equal("FileTooLarge", error.Code);
+        Assert.Equal("Photos must be 10 MB or smaller.", error.Message);
+        storage.VerifyNoOtherCalls();
+    }
+
+    [Fact]
+    public async Task AddMedia_PhotoDeclaredAsForeignVideoType_IsSizedAsAPhoto()
+    {
+        // A .jpg with a foreign video type resolves to image/jpeg for validation, so it must
+        // also be sized as a photo, not given the 100 MB video allowance.
+        var file = OversizeFile(60_000_000, "photo.jpg", "video/3gpp", JpegHeader);
+        var storage = new Mock<IFileStoragePort>(MockBehavior.Strict);
+        var controller = CreateController(storage: storage);
+
+        var result = await controller.AddMedia(1, null, file, CancellationToken.None);
+
+        var response = Assert.IsType<UnprocessableEntityObjectResult>(result);
+        var error = Assert.IsType<WorkOrderBoardValidationErrorDto>(response.Value);
+        Assert.Equal("FileTooLarge", error.Code);
+        Assert.Equal("Photos must be 10 MB or smaller.", error.Message);
+        storage.VerifyNoOtherCalls();
+    }
+
+    [Fact]
+    public async Task AddMedia_DocumentOverFiftyMegabytes_ReturnsStableUnprocessableEntity()
+    {
+        var file = OversizeFile(50_000_001, "report.pdf", "application/pdf", PdfHeader);
+        var storage = new Mock<IFileStoragePort>(MockBehavior.Strict);
+        var controller = CreateController(storage: storage);
+
+        var result = await controller.AddMedia(1, WorkOrderMediaCategory.Extra, file, CancellationToken.None);
+
+        var response = Assert.IsType<UnprocessableEntityObjectResult>(result);
+        var error = Assert.IsType<WorkOrderBoardValidationErrorDto>(response.Value);
+        Assert.Equal("FileTooLarge", error.Code);
+        Assert.Equal("Documents must be 50 MB or smaller.", error.Message);
+        storage.VerifyNoOtherCalls();
+    }
+
+    [Fact]
+    public async Task AddMedia_OversizeUnsupportedType_ReportsUnsupportedTypeNotOversizeVideo()
+    {
+        var file = OversizeFile(150_000_000, "payload.exe", "application/octet-stream", [0x4D, 0x5A]);
+        var storage = new Mock<IFileStoragePort>(MockBehavior.Strict);
+        var controller = CreateController(storage: storage);
+
+        var result = await controller.AddMedia(1, null, file, CancellationToken.None);
+
+        var response = Assert.IsType<UnprocessableEntityObjectResult>(result);
+        var error = Assert.IsType<WorkOrderBoardValidationErrorDto>(response.Value);
+        Assert.Equal("UnsupportedMediaType", error.Code);
+        storage.VerifyNoOtherCalls();
+    }
+
+    [Fact]
+    public void ValidateSize_OversizeUnknownKind_UsesTypeNeutralMessage()
+    {
+        Assert.Equal(
+            "Files must be 100 MB or smaller.",
+            WorkOrderMediaContract.ValidateSize(150_000_000, WorkOrderMediaContract.UploadKind.Unknown));
+    }
+
+    private static readonly byte[] FtypHeader = [0, 0, 0, 0x18, (byte)'f', (byte)'t', (byte)'y', (byte)'p', (byte)'i', (byte)'s', (byte)'o', (byte)'m'];
+    private static readonly byte[] JpegHeader = [0xFF, 0xD8, 0xFF, 0xE0];
+    private static readonly byte[] PdfHeader = [0x25, 0x50, 0x44, 0x46, 0x2D];
+
+    /// <summary>
+    /// A file that reports <paramref name="length"/> bytes but only backs the 512-byte header the
+    /// type rules read, so oversize cases run through real signature validation cheaply.
+    /// </summary>
+    private static FormFile OversizeFile(long length, string fileName, string contentType, byte[] header)
+    {
+        var bytes = new byte[512];
+        header.CopyTo(bytes, 0);
+        return new FormFile(new MemoryStream(bytes), 0, length, "file", fileName)
+        {
+            Headers = new HeaderDictionary(),
+            ContentType = contentType
+        };
+    }
+
+    private static FormFile VideoFormFile(int size, string fileName, string contentType)
+    {
+        var bytes = new byte[size];
+        // ISO BMFF ftyp box so the media type rules accept the payload as MP4/MOV.
+        bytes[4] = (byte)'f';
+        bytes[5] = (byte)'t';
+        bytes[6] = (byte)'y';
+        bytes[7] = (byte)'p';
+        bytes[8] = (byte)'i';
+        bytes[9] = (byte)'s';
+        bytes[10] = (byte)'o';
+        bytes[11] = (byte)'m';
+        return new FormFile(new MemoryStream(bytes), 0, bytes.Length, "file", fileName)
+        {
+            Headers = new HeaderDictionary(),
+            ContentType = contentType
+        };
+    }
+
+    private static (Mock<IWorkOrderMediaService> Service, Mock<IFileStoragePort> Storage) SetupSuccessfulAddMedia()
+    {
+        var service = new Mock<IWorkOrderMediaService>(MockBehavior.Strict);
+        service
+            .Setup(candidate => candidate.EnsureCanMutateMediaAsync(
+                1, It.IsAny<ClaimsPrincipal>(), It.IsAny<string?>(), It.IsAny<CancellationToken>(), null))
+            .Returns(Task.CompletedTask);
+        service
+            .Setup(candidate => candidate.AddMediaAsync(
+                1, null, "https://storage.test/stored", It.IsAny<ClaimsPrincipal>(), It.IsAny<string?>(),
+                It.IsAny<CancellationToken>()))
+            .ReturnsAsync(new WorkOrderMediaFileDto { Id = 5, Url = "https://storage.test/stored" });
+        var storage = new Mock<IFileStoragePort>(MockBehavior.Strict);
+        storage
+            .Setup(candidate => candidate.SaveFileAsync(It.IsAny<IFormFile>()))
+            .ReturnsAsync("https://storage.test/stored");
+        return (service, storage);
+    }
+
+    [Fact]
+    public async Task AddMedia_SixtyMegabyteMp4_IsAccepted()
+    {
+        var (service, storage) = SetupSuccessfulAddMedia();
+        var controller = CreateController(service, storage);
+        var file = VideoFormFile(60_000_000, "site-clip.mp4", "video/mp4");
+
+        var result = await controller.AddMedia(1, null, file, CancellationToken.None);
+
+        var ok = Assert.IsType<OkObjectResult>(result);
+        Assert.Equal(5, Assert.IsType<WorkOrderMediaFileDto>(ok.Value).Id);
+    }
+
+    [Fact]
+    public async Task AddMedia_VideoLongerThanNinetySeconds_ReturnsStableUnprocessableEntity()
+    {
+        var storage = new Mock<IFileStoragePort>(MockBehavior.Strict);
+        var controller = CreateController(storage: storage);
+        var file = PhoneVideo(durationSeconds: 95, "IMG_0042.MOV", "video/quicktime");
+
+        var result = await controller.AddMedia(1, null, file, CancellationToken.None);
+
+        var response = Assert.IsType<UnprocessableEntityObjectResult>(result);
+        var error = Assert.IsType<WorkOrderBoardValidationErrorDto>(response.Value);
+        Assert.Equal("VideoTooLong", error.Code);
+        Assert.Equal("Videos must be 90 seconds or shorter.", error.Message);
+        storage.VerifyNoOtherCalls();
+    }
+
+    [Fact]
+    public async Task AddMedia_VideoWithinNinetySeconds_IsAccepted()
+    {
+        var (service, storage) = SetupSuccessfulAddMedia();
+        var controller = CreateController(service, storage);
+        var file = PhoneVideo(durationSeconds: 60, "IMG_0043.MOV", "");
+
+        var result = await controller.AddMedia(1, null, file, CancellationToken.None);
+
+        Assert.IsType<OkObjectResult>(result);
+    }
+
+    /// <summary>ftyp + mdat + moov/mvhd (moov last, as phones write it).</summary>
+    private static FormFile PhoneVideo(uint durationSeconds, string fileName, string contentType)
+    {
+        static byte[] Box(string type, byte[] body)
+        {
+            var box = new byte[8 + body.Length];
+            System.Buffers.Binary.BinaryPrimitives.WriteUInt32BigEndian(box, (uint)box.Length);
+            System.Text.Encoding.ASCII.GetBytes(type).CopyTo(box, 4);
+            body.CopyTo(box, 8);
+            return box;
+        }
+
+        var mvhd = new byte[20];
+        System.Buffers.Binary.BinaryPrimitives.WriteUInt32BigEndian(mvhd.AsSpan(12), 1000);
+        System.Buffers.Binary.BinaryPrimitives.WriteUInt32BigEndian(mvhd.AsSpan(16), durationSeconds * 1000);
+        var bytes = Box("ftyp", System.Text.Encoding.ASCII.GetBytes("qt  \0\0\0\0"))
+            .Concat(Box("mdat", new byte[4096]))
+            .Concat(Box("moov", Box("mvhd", mvhd)))
+            .ToArray();
+        return new FormFile(new MemoryStream(bytes), 0, bytes.Length, "file", fileName)
+        {
+            Headers = new HeaderDictionary(),
+            ContentType = contentType
+        };
+    }
+
+    [Fact]
+    public async Task AddMedia_SixtyMegabyteQuicktimeMov_IsAccepted()
+    {
+        var (service, storage) = SetupSuccessfulAddMedia();
+        var controller = CreateController(service, storage);
+        var file = VideoFormFile(60_000_000, "site-clip.mov", "video/quicktime");
+
+        var result = await controller.AddMedia(1, null, file, CancellationToken.None);
+
+        Assert.IsType<OkObjectResult>(result);
+    }
+
+    [Fact]
+    public async Task AddMedia_SixtyMegabyteMovWithEmptyContentType_IsAccepted()
+    {
+        var (service, storage) = SetupSuccessfulAddMedia();
+        var controller = CreateController(service, storage);
+        var file = VideoFormFile(60_000_000, "site-clip.MOV", "");
+
+        var result = await controller.AddMedia(1, null, file, CancellationToken.None);
+
+        Assert.IsType<OkObjectResult>(result);
+    }
+
+    [Fact]
+    public async Task AddMedia_SixtyMegabyteMp4WithOctetStreamContentType_IsAccepted()
+    {
+        var (service, storage) = SetupSuccessfulAddMedia();
+        var controller = CreateController(service, storage);
+        var file = VideoFormFile(60_000_000, "site-clip.mp4", "application/octet-stream");
+
+        var result = await controller.AddMedia(1, null, file, CancellationToken.None);
+
+        Assert.IsType<OkObjectResult>(result);
+    }
+
+    [Fact]
+    public async Task AddMedia_HeicPhoto_IsAccepted()
+    {
+        var (service, storage) = SetupSuccessfulAddMedia();
+        var controller = CreateController(service, storage);
+        var bytes = new byte[512];
+        bytes[4] = (byte)'f';
+        bytes[5] = (byte)'t';
+        bytes[6] = (byte)'y';
+        bytes[7] = (byte)'p';
+        bytes[8] = (byte)'h';
+        bytes[9] = (byte)'e';
+        bytes[10] = (byte)'i';
+        bytes[11] = (byte)'c';
+        var file = new FormFile(new MemoryStream(bytes), 0, bytes.Length, "file", "capture.heic")
+        {
+            Headers = new HeaderDictionary(),
+            ContentType = "image/heic"
+        };
+
+        var result = await controller.AddMedia(1, null, file, CancellationToken.None);
+
+        Assert.IsType<OkObjectResult>(result);
+    }
+
     [Fact]
     public async Task AddMedia_UnsupportedType_ReturnsUnprocessableEntity()
     {
@@ -167,7 +425,8 @@ public class WorkOrderMediaServiceCancellationTests
             mediaData.Object,
             new Mock<IWorkOrderDetailDataService>(MockBehavior.Strict).Object,
             new Mock<IWorkOrderAuditService>(MockBehavior.Strict).Object,
-            storage.Object);
+            storage.Object,
+            new Mock<IUpliftDataService>(MockBehavior.Strict).Object);
         var user = new ClaimsPrincipal(new ClaimsIdentity(
             new[]
             {
@@ -184,4 +443,37 @@ public class WorkOrderMediaServiceCancellationTests
         mediaData.Verify(candidate => candidate.GetAttachmentForReadAsync(10, 1, token), Times.Once);
         mediaData.VerifyNoOtherCalls();
     }
+
+    [Fact]
+    public async Task GetMediaContent_ServesHeicAsImageHeic()
+    {
+        const string url = "https://example.test/Assets/Images/photo.heic";
+        var mediaData = new Mock<IWorkOrderMediaDataService>(MockBehavior.Strict);
+        mediaData.Setup(candidate => candidate.GetWorkOrderForMediaAuthAsync(1, null, It.IsAny<CancellationToken>()))
+            .ReturnsAsync(new WorkOrder { Id = 1 });
+        mediaData.Setup(candidate => candidate.GetAttachmentForReadAsync(10, 1, It.IsAny<CancellationToken>()))
+            .ReturnsAsync(new WorkOrderAttachments { Id = 10, WorkorderId = 1, Attachments = url });
+        var storage = new Mock<IFileStoragePort>(MockBehavior.Strict);
+        storage.Setup(candidate => candidate.OpenRead(url)).Returns(new MemoryStream([1, 2, 3]));
+        var service = new WorkOrderMediaService(
+            mediaData.Object,
+            new Mock<IWorkOrderDetailDataService>(MockBehavior.Strict).Object,
+            new Mock<IWorkOrderAuditService>(MockBehavior.Strict).Object,
+            storage.Object,
+            new Mock<IUpliftDataService>(MockBehavior.Strict).Object);
+        var user = new ClaimsPrincipal(new ClaimsIdentity(
+            new[]
+            {
+                new Claim(ClaimTypes.NameIdentifier, "actor-1"),
+                new Claim(ClaimTypes.Role, "Admin"),
+                new Claim(SeaHavenClaimTypes.OrgScope, SeaHavenClaimTypes.OrgScopeAll)
+            },
+            "Test"));
+
+        var result = await service.GetMediaContentAsync(1, 10, user, "actor-1");
+        result.Content.Dispose();
+
+        Assert.Equal("image/heic", result.ContentType);
+        Assert.Equal("photo.heic", result.FileName);
+    }
 }

Api.SeaHavenIndustries/Controllers/VendorPortalController.cs

@@ -5,6 +5,7 @@ using Microsoft.AspNetCore.Mvc;
 using Microsoft.Extensions.Logging;
 using SeaHaven.Services.DTOs;
 using SeaHaven.Services.Exceptions;
+using SeaHaven.Services.Helpers;
 using SeaHaven.Services.Interfaces;
 
 namespace Api.SeaHavenIndustries.Controllers
@@ -299,7 +300,7 @@ namespace Api.SeaHavenIndustries.Controllers
 
         [HttpPost("dispatches/{id:int}/completion-documents")]
         [HttpPost("dispatches/{id:int}/documents")]
-        [RequestSizeLimit(10_000_000)]
+        [RequestSizeLimit(WorkOrderMediaContract.MaxUploadRequestBytes)]
         public async Task<IActionResult> UploadCompletionDocument(
             int id,
             [FromForm] IFormFile file,

Api.SeaHavenIndustries/Controllers/WorkOrderMediaController.cs

@@ -17,7 +17,7 @@ namespace Api.SeaHavenIndustries.Controllers
     [Route("api/workorders")]
     public class WorkOrderMediaController : Controller
     {
-        public const long MaxUploadBytes = 200_000_000;
+        public const long MaxUploadBytes = WorkOrderMediaContract.MaxUploadRequestBytes;
 
         private readonly IWorkOrderMediaService _workOrderMediaService;
         private readonly IFileStoragePort _fileStorage;
@@ -88,14 +88,28 @@ namespace Api.SeaHavenIndustries.Controllers
             string? fileUrl = null;
             try
             {
-                if (file.Length > MaxUploadBytes)
+                // Type first, so an unsupported file always reports UnsupportedMediaType instead
+                // of being sized under a kind it does not have.
+                WorkOrderMediaFileRules.EnsureAllowed(file, category);
+
+                // Media contract: per-kind caps (photos 10 MB, videos 100 MB, documents 50 MB).
+                // Classify by the same resolved type EnsureAllowed validates against.
+                var sizeMessage = WorkOrderMediaContract.ValidateSize(
+                    WorkOrderMediaFileRules.ResolveUploadContentType(file), file.FileName, file.Length);
+                if (sizeMessage != null)
                 {
-                    throw new WorkOrderBoardValidationException(
-                        "FileTooLarge",
-                        "The uploaded file must not exceed 200 MB.");
+                    throw new WorkOrderBoardValidationException("FileTooLarge", sizeMessage);
                 }
 
-                WorkOrderMediaFileRules.EnsureAllowed(file, category);
+                if (WorkOrderMediaContract.ResolveKind(
+                        WorkOrderMediaFileRules.ResolveUploadContentType(file), file.FileName)
+                    == WorkOrderMediaContract.UploadKind.Video)
+                {
+                    using var content = file.OpenReadStream();
+                    var durationMessage = WorkOrderMediaContract.ValidateVideoDuration(content);
+                    if (durationMessage != null)
+                        throw new WorkOrderBoardValidationException("VideoTooLong", durationMessage);
+                }
                 var actorId = User.FindFirstValue(ClaimTypes.NameIdentifier);
                 await _workOrderMediaService.EnsureCanMutateMediaAsync(id, User, actorId, cancellationToken, category);
 

SeaHaven.DataServices/Implementation/VendorDocumentDataService.cs

@@ -17,6 +17,39 @@ namespace SeaHaven.DataServices.Implementation
         // supporting evidence never participates in completion versioning or replacement.
         private const string CompletionPurpose = "Completion";
 
+        public async Task<IReadOnlyList<string>> ListActiveContentTypesForWorkOrderAsync(
+            int workOrderId,
+            int? excludingDocumentId,
+            CancellationToken cancellationToken)
+        {
+            // Uplift evidence also records the latest completion id in ReplacesDocumentId, so only
+            // a newer completion version supersedes a document.
+            return await _context.VendorCompletionDocuments
+                .AsNoTracking()
+                .Where(document => document.WorkOrderId == workOrderId
+                    && (document.IsDeleted == null || document.IsDeleted == false)
+                    && (excludingDocumentId == null || document.Id != excludingDocumentId)
+                    && !_context.VendorCompletionDocuments.Any(newer =>
+                        newer.ReplacesDocumentId == document.Id
+                        && newer.Purpose == CompletionPurpose
+                        && (newer.IsDeleted == null || newer.IsDeleted == false)))
+                .Select(document => document.ContentType)
+                .ToListAsync(cancellationToken);
+        }
+
+        public async Task<IReadOnlyList<string>> ListActiveWorkOrderAttachmentUrlsAsync(
+            int workOrderId,
+            CancellationToken cancellationToken)
+        {
+            return await _context.workOrderAttachments
+                .AsNoTracking()
+                .Where(attachment => attachment.WorkorderId == workOrderId
+                    && attachment.IsDeleted != true
+                    && attachment.Attachments != null)
+                .Select(attachment => attachment.Attachments!)
+                .ToListAsync(cancellationToken);
+        }
+
         public Task<VendorCompletionDocument?> GetLatestForDispatchAsync(int dispatchId, CancellationToken cancellationToken)
         {
             return _context.VendorCompletionDocuments

SeaHaven.DataServices/Implementation/WorkOrderMediaDataService.cs

@@ -56,6 +56,36 @@ namespace SeaHaven.DataServices.Implementation
         public void TrackAttachment(WorkOrderAttachments attachment)
             => _context.workOrderAttachments.Add(attachment);
 
+        public async Task<IReadOnlyList<string>> ListActiveAttachmentUrlsAsync(
+            int workOrderId,
+            CancellationToken cancellationToken)
+        {
+            var urls = await _context.workOrderAttachments
+                .AsNoTracking()
+                .Where(a => a.WorkorderId == workOrderId && a.IsDeleted != true && a.Attachments != null)
+                .Select(a => a.Attachments!)
+                .ToListAsync(cancellationToken);
+            return urls;
+        }
+
+        public async Task<IReadOnlyList<string>> ListActiveVendorMediaContentTypesAsync(
+            int workOrderId,
+            CancellationToken cancellationToken)
+        {
+            // Uplift evidence also records the latest completion id in ReplacesDocumentId, so only
+            // a newer completion version supersedes a document.
+            return await _context.VendorCompletionDocuments
+                .AsNoTracking()
+                .Where(document => document.WorkOrderId == workOrderId
+                    && (document.IsDeleted == null || document.IsDeleted == false)
+                    && !_context.VendorCompletionDocuments.Any(newer =>
+                        newer.ReplacesDocumentId == document.Id
+                        && newer.Purpose == "Completion"
+                        && (newer.IsDeleted == null || newer.IsDeleted == false)))
+                .Select(document => document.ContentType)
+                .ToListAsync(cancellationToken);
+        }
+
         public void SetExpectedWorkOrderVersion(WorkOrder workOrder, byte[] version)
             => _context.Entry(workOrder).Property(w => w.RowVersion).OriginalValue = version;
 

SeaHaven.DataServices/Interfaces/IVendorDocumentDataService.cs

@@ -9,6 +9,19 @@ namespace SeaHaven.DataServices.Interfaces
         Task<VendorCompletionDocument?> GetMetadataForVendorDispatchAsync(int documentId, int dispatchId, int vendorId, CancellationToken cancellationToken);
         Task<List<VendorCompletionDocument>> ListForVendorDispatchAsync(int dispatchId, int vendorId, CancellationToken cancellationToken);
         Task<VendorCompletionDocument?> GetUpliftEvidenceAsync(int documentId, int dispatchId, int vendorId, CancellationToken cancellationToken);
+        /// <summary>
+        /// Content types of the work order's current vendor documents (not deleted, not replaced by a
+        /// newer completion version), optionally excluding one being replaced. Feeds the per-work-order photo/video counts.
+        /// </summary>
+        Task<IReadOnlyList<string>> ListActiveContentTypesForWorkOrderAsync(
+            int workOrderId,
+            int? excludingDocumentId,
+            CancellationToken cancellationToken);
+
+        /// <summary>Stored URLs of the work order's non-deleted dispatcher attachments (photo/video counts).</summary>
+        Task<IReadOnlyList<string>> ListActiveWorkOrderAttachmentUrlsAsync(
+            int workOrderId,
+            CancellationToken cancellationToken);
         Task AddAsync(VendorCompletionDocument document, CancellationToken cancellationToken);
         Task SaveChangesAsync(CancellationToken cancellationToken);
     }

SeaHaven.DataServices/Interfaces/IWorkOrderMediaDataService.cs

@@ -22,6 +22,19 @@ namespace SeaHaven.DataServices.Interfaces
 
         Task<WorkOrderAttachments?> GetTrackedAttachmentAsync(int mediaId, int workOrderId, CancellationToken cancellationToken);
         void TrackAttachment(WorkOrderAttachments attachment);
+
+        /// <summary>Stored URLs of the work order's non-deleted attachments (photo/video counts).</summary>
+        Task<IReadOnlyList<string>> ListActiveAttachmentUrlsAsync(
+            int workOrderId,
+            CancellationToken cancellationToken);
+
+        /// <summary>
+        /// Content types of the work order's current vendor-portal documents (not deleted, not
+        /// replaced by a newer completion version). The counts span both upload surfaces.
+        /// </summary>
+        Task<IReadOnlyList<string>> ListActiveVendorMediaContentTypesAsync(
+            int workOrderId,
+            CancellationToken cancellationToken);
         void SetExpectedWorkOrderVersion(WorkOrder workOrder, byte[] version);
         void MarkWorkOrderModified(WorkOrder workOrder);
         Task SaveAsync(CancellationToken cancellationToken);

SeaHaven.Services/DTOs/VendorPortalServiceDTOs.cs

@@ -136,6 +136,26 @@ namespace SeaHaven.Services.DTOs
         public IEnumerable<PortalCommentDTO> Comments { get; set; } = Enumerable.Empty<PortalCommentDTO>();
         public IEnumerable<PortalUpliftDTO> UpliftRequests { get; set; } = Enumerable.Empty<PortalUpliftDTO>();
         public IEnumerable<VendorPortalDocumentDTO> Documents { get; set; } = Enumerable.Empty<VendorPortalDocumentDTO>();
+        public PortalMediaCountsDTO? MediaCounts { get; set; }
+    }
+
+    /// <summary>
+    /// Per-work-order photo/video usage, so the portal can pre-check an upload
+    /// before sending it. The server still enforces the limit on upload.
+    /// </summary>
+    public class PortalMediaCountsDTO
+    {
+        public int MaxPhotos { get; set; }
+        public int MaxVideos { get; set; }
+        /// <summary>Photos/videos on the work order, counted for evidence uploads.</summary>
+        public int Photos { get; set; }
+        public int Videos { get; set; }
+        /// <summary>
+        /// Photos/videos counted for a new completion version, which replaces the dispatch's
+        /// latest document and so does not count it.
+        /// </summary>
+        public int CompletionPhotos { get; set; }
+        public int CompletionVideos { get; set; }
     }
 
     public class VendorPortalDocumentDTO

SeaHaven.Services/Helpers/VideoDurationProbe.cs

@@ -0,0 +1,129 @@
+using System.Buffers.Binary;
+using System.Text;
+
+namespace SeaHaven.Services.Helpers
+{
+    /// <summary>
+    /// Reads a video's duration from the ISO base media (MP4 / QuickTime) movie header:
+    /// top-level <c>moov</c> box → <c>mvhd</c> timescale and duration. It seeks over box
+    /// headers only (the <c>moov</c> box may sit after a large <c>mdat</c>), never decodes
+    /// media and never allocates more than a few bytes. Returns null whenever the structure
+    /// cannot be read, so callers can let unreadable files through (per the media contract: unreadable
+    /// metadata never blocks an upload).
+    /// </summary>
+    public static class VideoDurationProbe
+    {
+        private const int MaxBoxesPerLevel = 1024;
+
+        public static double? TryReadDurationSeconds(Stream? stream)
+        {
+            if (stream == null || !stream.CanSeek || !stream.CanRead)
+                return null;
+
+            try
+            {
+                var moov = FindBox(stream, 0, stream.Length, "moov");
+                if (moov == null)
+                    return null;
+
+                var mvhd = FindBox(stream, moov.Value.BodyStart, moov.Value.End, "mvhd");
+                return mvhd == null ? null : ReadMovieHeaderSeconds(stream, mvhd.Value);
+            }
+            catch (IOException)
+            {
+                return null;
+            }
+        }
+
+        private readonly record struct Box(long BodyStart, long End);
+
+        private static Box? FindBox(Stream stream, long start, long end, string type)
+        {
+            var header = new byte[8];
+            var position = start;
+            for (var i = 0; i < MaxBoxesPerLevel && position + 8 <= end; i++)
+            {
+                stream.Position = position;
+                if (!ReadExactly(stream, header, 8))
+                    return null;
+
+                long size = BinaryPrimitives.ReadUInt32BigEndian(header);
+                var boxType = Encoding.ASCII.GetString(header, 4, 4);
+                var headerLength = 8;
+                if (size == 1)
+                {
+                    // 64-bit "largesize" follows the type.
+                    var large = new byte[8];
+                    if (!ReadExactly(stream, large, 8))
+                        return null;
+                    var largeSize = BinaryPrimitives.ReadUInt64BigEndian(large);
+                    if (largeSize > long.MaxValue)
+                        return null;
+                    size = (long)largeSize;
+                    headerLength = 16;
+                }
+                else if (size == 0)
+                {
+                    size = end - position;
+                }
+
+                if (size < headerLength || position + size > end)
+                    return null;
+
+                if (boxType == type)
+                    return new Box(position + headerLength, position + size);
+
+                position += size;
+            }
+
+            return null;
+        }
+
+        private static double? ReadMovieHeaderSeconds(Stream stream, Box mvhd)
+        {
+            // version(1) flags(3), then v0: creation(4) modification(4) timescale(4) duration(4)
+            //                          v1: creation(8) modification(8) timescale(4) duration(8)
+            var body = new byte[32];
+            stream.Position = mvhd.BodyStart;
+            var available = (int)Math.Min(body.Length, mvhd.End - mvhd.BodyStart);
+            if (available < 20 || !ReadExactly(stream, body, available))
+                return null;
+
+            uint timescale;
+            ulong duration;
+            if (body[0] == 0)
+            {
+                timescale = BinaryPrimitives.ReadUInt32BigEndian(body.AsSpan(12, 4));
+                duration = BinaryPrimitives.ReadUInt32BigEndian(body.AsSpan(16, 4));
+            }
+            else if (body[0] == 1 && available >= 32)
+            {
+                timescale = BinaryPrimitives.ReadUInt32BigEndian(body.AsSpan(20, 4));
+                duration = BinaryPrimitives.ReadUInt64BigEndian(body.AsSpan(24, 8));
+            }
+            else
+            {
+                return null;
+            }
+
+            // All-ones duration means "unknown" in the spec.
+            if (timescale == 0 || duration == uint.MaxValue || duration == ulong.MaxValue)
+                return null;
+
+            return (double)duration / timescale;
+        }
+
+        private static bool ReadExactly(Stream stream, byte[] buffer, int count)
+        {
+            var read = 0;
+            while (read < count)
+            {
+                var n = stream.Read(buffer, read, count - read);
+                if (n <= 0)
+                    return false;
+                read += n;
+            }
+            return true;
+        }
+    }
+}

SeaHaven.Services/Helpers/WorkOrderMediaContract.cs

@@ -0,0 +1,149 @@
+namespace SeaHaven.Services.Helpers
+{
+    /// <summary>
+    /// Client-confirmed media contract (2026-09-22): photos up to 10 MB (JPEG/PNG/HEIC),
+    /// videos up to 100 MB and 90 seconds (MP4/MOV), at most 10 photos and 3 videos per work
+    /// order, across the dispatcher media modal, the completion-doc media tab and the vendor
+    /// portal upload. Documents (PDF/DOC/DOCX) keep the 50 MB document cap. Duration is read
+    /// from the MP4/MOV movie header (<see cref="VideoDurationProbe"/>); the browser pre-checks
+    /// it and the server enforces it, and unreadable metadata never blocks an upload.
+    /// </summary>
+    public static class WorkOrderMediaContract
+    {
+        public const long MaxPhotoBytes = 10_000_000;
+        public const long MaxVideoBytes = 100_000_000;
+        public const long MaxDocumentBytes = 50_000_000;
+        public const int MaxPhotosPerWorkOrder = 10;
+        public const int MaxVideosPerWorkOrder = 3;
+        public const int MaxVideoDurationSeconds = 90;
+
+        /// <summary>
+        /// Request-level ceiling for media endpoints (RequestSizeLimit / multipart limit). It sits
+        /// above <see cref="MaxVideoBytes"/> plus multipart overhead so an oversize file reaches the
+        /// per-kind check and gets its generic message instead of a framework 413. The EB nginx
+        /// proxy (.platform/nginx/conf.d/01_upload_body_size.conf) must stay above this value.
+        /// </summary>
+        public const long MaxUploadRequestBytes = 110_000_000;
+
+        public enum UploadKind
+        {
+            Photo,
+            Video,
+            Document,
+            Unknown
+        }
+
+        private static readonly Dictionary<string, UploadKind> KindByContentType =
+            new(StringComparer.OrdinalIgnoreCase)
+            {
+                ["image/jpeg"] = UploadKind.Photo,
+                ["image/jpg"] = UploadKind.Photo,
+                ["image/png"] = UploadKind.Photo,
+                ["image/heic"] = UploadKind.Photo,
+                ["video/mp4"] = UploadKind.Video,
+                ["video/quicktime"] = UploadKind.Video,
+                ["application/pdf"] = UploadKind.Document,
+                ["application/msword"] = UploadKind.Document,
+                ["application/vnd.openxmlformats-officedocument.wordprocessingml.document"] =
+                    UploadKind.Document,
+            };
+
+        private static readonly Dictionary<string, UploadKind> KindByExtension =
+            new(StringComparer.OrdinalIgnoreCase)
+            {
+                [".jpg"] = UploadKind.Photo,
+                [".jpeg"] = UploadKind.Photo,
+                [".png"] = UploadKind.Photo,
+                [".heic"] = UploadKind.Photo,
+                [".mp4"] = UploadKind.Video,
+                [".mov"] = UploadKind.Video,
+                [".pdf"] = UploadKind.Document,
+                [".doc"] = UploadKind.Document,
+                [".docx"] = UploadKind.Document,
+            };
+
+        /// <summary>
+        /// Classifies an upload. Pass the validated (resolved) content type: it decides whenever
+        /// it is an allowlisted type, so a misleading file name cannot move a file into a larger
+        /// size class. The extension only decides when no allowlisted type is known (for example
+        /// counting stored attachment URLs).
+        /// </summary>
+        public static UploadKind ResolveKind(string? contentType, string? fileName)
+        {
+            var type = (contentType ?? string.Empty).Trim();
+            if (KindByContentType.TryGetValue(type, out var byType))
+                return byType;
+
+            var extension = Path.GetExtension(fileName ?? string.Empty);
+            return KindByExtension.TryGetValue(extension, out var byExtension)
+                ? byExtension
+                : UploadKind.Unknown;
+        }
+
+        /// <summary>
+        /// Per-work-order count check across both upload surfaces: dispatcher attachments
+        /// (classified by stored URL) and vendor-portal documents (classified by validated
+        /// content type). Returns the stable rejection message, or null when there is room.
+        /// </summary>
+        public static string? ValidateCount(
+            UploadKind kind,
+            IEnumerable<string> attachmentUrls,
+            IEnumerable<string> vendorContentTypes)
+        {
+            if (kind != UploadKind.Photo && kind != UploadKind.Video)
+                return null;
+
+            var (photos, videos) = CountKinds(attachmentUrls, vendorContentTypes);
+
+            if (kind == UploadKind.Photo && photos >= MaxPhotosPerWorkOrder)
+                return "A work order can have at most 10 photos.";
+            if (kind == UploadKind.Video && videos >= MaxVideosPerWorkOrder)
+                return "A work order can have at most 3 videos.";
+            return null;
+        }
+
+        /// <summary>
+        /// Photos and videos on a work order: dispatcher attachments (kind from the stored URL)
+        /// plus current vendor-portal documents (kind from the validated content type).
+        /// </summary>
+        public static (int Photos, int Videos) CountKinds(
+            IEnumerable<string> attachmentUrls,
+            IEnumerable<string> vendorContentTypes)
+        {
+            var kinds = attachmentUrls.Select(url => ResolveKind(null, url))
+                .Concat(vendorContentTypes.Select(type => ResolveKind(type, null)))
+                .ToList();
+            return (kinds.Count(k => k == UploadKind.Photo), kinds.Count(k => k == UploadKind.Video));
+        }
+
+        /// <summary>
+        /// 90-second video limit, read from the MP4/QuickTime movie header. A video whose
+        /// duration cannot be read is not blocked. Returns the stable message or null.
+        /// </summary>
+        public static string? ValidateVideoDuration(Stream? content)
+        {
+            var seconds = VideoDurationProbe.TryReadDurationSeconds(content);
+            return seconds > MaxVideoDurationSeconds
+                ? $"Videos must be {MaxVideoDurationSeconds} seconds or shorter."
+                : null;
+        }
+
+        /// <summary>Stable, generic per-kind size message; never echoes file metadata.</summary>
+        public static string? ValidateSize(long length, UploadKind kind)
+        {
+            return kind switch
+            {
+                UploadKind.Photo when length > MaxPhotoBytes => "Photos must be 10 MB or smaller.",
+                UploadKind.Video when length > MaxVideoBytes => "Videos must be 100 MB or smaller.",
+                UploadKind.Document when length > MaxDocumentBytes =>
+                    "Documents must be 50 MB or smaller.",
+                UploadKind.Unknown when length > MaxVideoBytes =>
+                    "Files must be 100 MB or smaller.",
+                _ => null
+            };
+        }
+
+        public static string? ValidateSize(string? contentType, string? fileName, long length)
+            => ValidateSize(length, ResolveKind(contentType, fileName));
+    }
+}

SeaHaven.Services/Helpers/WorkOrderMediaFileRules.cs

@@ -12,6 +12,7 @@ namespace SeaHaven.Services.Helpers
             "image/jpeg",
             "image/jpg",
             "image/png",
+            "image/heic",
             "video/mp4",
             "video/quicktime",
             "application/pdf",
@@ -24,6 +25,7 @@ namespace SeaHaven.Services.Helpers
             {
                 ["image/jpeg"] = new HashSet<string>(StringComparer.OrdinalIgnoreCase) { ".jpg", ".jpeg" },
                 ["image/png"] = new HashSet<string>(StringComparer.OrdinalIgnoreCase) { ".png" },
+                ["image/heic"] = new HashSet<string>(StringComparer.OrdinalIgnoreCase) { ".heic" },
                 ["video/mp4"] = new HashSet<string>(StringComparer.OrdinalIgnoreCase) { ".mp4" },
                 ["video/quicktime"] = new HashSet<string>(StringComparer.OrdinalIgnoreCase) { ".mov" },
                 ["application/pdf"] = new HashSet<string>(StringComparer.OrdinalIgnoreCase) { ".pdf" },
@@ -42,7 +44,11 @@ namespace SeaHaven.Services.Helpers
         // the accepted set of files.
         private static string? ResolveContentType(string declaredType, string extension)
         {
-            if (AllowedContentTypes.Contains(declaredType))
+            // iOS transcodes a picked HEIC photo to JPEG (named .jpg) but can keep image/heic as
+            // its type, so a declared image/heic is only authoritative on a real .heic file.
+            var isTranscodedHeic = declaredType.Equals("image/heic", StringComparison.OrdinalIgnoreCase)
+                && !extension.Equals(".heic", StringComparison.OrdinalIgnoreCase);
+            if (AllowedContentTypes.Contains(declaredType) && !isTranscodedHeic)
                 return declaredType;
 
             foreach (var (contentType, extensions) in ExtensionsByContentType)
@@ -61,6 +67,19 @@ namespace SeaHaven.Services.Helpers
             return contentType;
         }
 
+        /// <summary>
+        /// The canonical content type <see cref="IsAllowed"/> validates the file as, or null when
+        /// no allowlisted type applies. Size classification must use this same type so a declared
+        /// type or a misleading extension cannot move a file into a larger size class.
+        /// </summary>
+        public static string? ResolveUploadContentType(IFormFile file)
+        {
+            var declaredType = (file.ContentType ?? string.Empty).Trim();
+            var extension = Path.GetExtension(file.FileName ?? string.Empty);
+            var resolvedType = ResolveContentType(declaredType, extension);
+            return resolvedType == null ? null : CanonicalContentType(resolvedType);
+        }
+
         public static bool IsAllowed(
             IFormFile file,
             WorkOrderMediaCategory? category = WorkOrderMediaCategory.Extra)
@@ -68,13 +87,11 @@ namespace SeaHaven.Services.Helpers
             if (file == null || file.Length <= 0)
                 return false;
 
-            var declaredType = (file.ContentType ?? string.Empty).Trim();
             var extension = Path.GetExtension(file.FileName ?? string.Empty);
-            var resolvedType = ResolveContentType(declaredType, extension);
-            if (resolvedType == null)
+            var contentType = ResolveUploadContentType(file);
+            if (contentType == null)
                 return false;
 
-            var contentType = CanonicalContentType(resolvedType);
             var resolvedCategory = category ?? WorkOrderMediaCategory.Extra;
             if (IsDocument(contentType)
                 && resolvedCategory is not WorkOrderMediaCategory.Extra and not WorkOrderMediaCategory.Aveta)
@@ -123,7 +140,7 @@ namespace SeaHaven.Services.Helpers
             {
                 throw new Exceptions.WorkOrderBoardValidationException(
                     "UnsupportedMediaType",
-                    "Supported file types are JPG, PNG, MP4, MOV, PDF, DOC, and DOCX for Extra Docs; photos accept media only.");
+                    "Supported file types are JPG, PNG, HEIC, MP4, MOV, PDF, DOC, and DOCX for Extra Docs; photos accept media only.");
             }
         }
 
@@ -139,6 +156,11 @@ namespace SeaHaven.Services.Helpers
                     && bytes[4] == 0x0D && bytes[5] == 0x0A && bytes[6] == 0x1A && bytes[7] == 0x0A;
             }
 
+            if (contentType.Equals("image/heic", StringComparison.OrdinalIgnoreCase))
+            {
+                return IsHeifBrand(bytes);
+            }
+
             if (contentType.Equals("image/jpeg", StringComparison.OrdinalIgnoreCase))
             {
                 return bytes.Length >= 3 && bytes[0] == 0xFF && bytes[1] == 0xD8 && bytes[2] == 0xFF;
@@ -206,5 +228,20 @@ namespace SeaHaven.Services.Helpers
                 && bytes[6] == (byte)'y'
                 && bytes[7] == (byte)'p';
         }
+
+        private static bool IsHeifBrand(byte[] bytes)
+        {
+            if (!HasFtypBox(bytes))
+                return false;
+
+            // HEIC/HEIF containers identify by the ftyp major brand (bytes 8..11).
+            var brand = System.Text.Encoding.ASCII.GetString(bytes, 8, 4);
+            return brand switch
+            {
+                "heic" or "heix" or "hevc" or "hevx" or "heim" or "heis" or "hevm" or "hevs"
+                    or "mif1" or "msf1" => true,
+                _ => false
+            };
+        }
     }
 }

SeaHaven.Services/Implementation/VendorPortalService.cs

@@ -5,6 +5,7 @@ using SeaHaven.DataServices.Interfaces;
 using SeaHaven.Services.Configuration;
 using SeaHaven.Services.DTOs;
 using SeaHaven.Services.Exceptions;
+using SeaHaven.Services.Helpers;
 using SeaHaven.Services.Interfaces;
 
 namespace SeaHaven.Services.Implementation
@@ -13,9 +14,36 @@ namespace SeaHaven.Services.Implementation
     {
         private static readonly HashSet<string> AllowedContentTypes = new(StringComparer.OrdinalIgnoreCase)
         {
-            "application/pdf", "image/jpeg", "image/jpg", "image/png"
+            "application/pdf", "image/jpeg", "image/jpg", "image/png", "image/heic",
+            "video/mp4", "video/quicktime"
         };
 
+        // The browser's File.type is unreliable on mobile (empty or application/octet-stream),
+        // so an extension pairing against the same allowlist resolves the real content type.
+        private static string? ResolveUploadContentType(IFormFile file)
+        {
+            var declaredType = (file.ContentType ?? string.Empty).Trim();
+            var extension = Path.GetExtension(file.FileName ?? string.Empty);
+            // iOS transcodes a picked HEIC photo to JPEG (named .jpg) but can keep image/heic.
+            var isTranscodedHeic = declaredType.Equals("image/heic", StringComparison.OrdinalIgnoreCase)
+                && !extension.Equals(".heic", StringComparison.OrdinalIgnoreCase);
+            if (AllowedContentTypes.Contains(declaredType) && !isTranscodedHeic)
+                return declaredType.Equals("image/jpg", StringComparison.OrdinalIgnoreCase)
+                    ? "image/jpeg"
+                    : declaredType;
+
+            return extension.ToLowerInvariant() switch
+            {
+                ".pdf" => "application/pdf",
+                ".jpg" or ".jpeg" => "image/jpeg",
+                ".png" => "image/png",
+                ".heic" => "image/heic",
+                ".mp4" => "video/mp4",
+                ".mov" => "video/quicktime",
+                _ => null
+            };
+        }
+
         private const int MaxRefusalReasonLength = 500;
 
         private readonly IVendorPortalTokenService _tokens;
@@ -180,8 +208,37 @@ namespace SeaHaven.Services.Implementation
                 }
             }
 
+            PortalMediaCountsDTO? mediaCounts = null;
+            if (dispatch.WorkOrderId is int workOrderId)
+            {
+                // Same basis as the upload check: a new completion version replaces the
+                // dispatch's latest document, so that one is not counted for it.
+                var attachmentUrls = await _documentData.ListActiveWorkOrderAttachmentUrlsAsync(
+                    workOrderId, cancellationToken);
+                var vendorTypes = await _documentData.ListActiveContentTypesForWorkOrderAsync(
+                    workOrderId, null, cancellationToken);
+                var latest = await _documentData.GetLatestForDispatchAsync(id, cancellationToken);
+                var completionTypes = latest == null
+                    ? vendorTypes
+                    : await _documentData.ListActiveContentTypesForWorkOrderAsync(
+                        workOrderId, latest.Id, cancellationToken);
+                var (photos, videos) = WorkOrderMediaContract.CountKinds(attachmentUrls, vendorTypes);
+                var (completionPhotos, completionVideos) =
+                    WorkOrderMediaContract.CountKinds(attachmentUrls, completionTypes);
+                mediaCounts = new PortalMediaCountsDTO
+                {
+                    MaxPhotos = WorkOrderMediaContract.MaxPhotosPerWorkOrder,
+                    MaxVideos = WorkOrderMediaContract.MaxVideosPerWorkOrder,
+                    Photos = photos,
+                    Videos = videos,
+                    CompletionPhotos = completionPhotos,
+                    CompletionVideos = completionVideos
+                };
+            }
+
             return new VendorDispatchDetailDTO
             {
+                MediaCounts = mediaCounts,
                 Id = dispatch.Id,
                 DispatchNumber = dispatch.DispatchNumber,
                 PONumber = dispatch.PONumber,
@@ -833,15 +890,31 @@ namespace SeaHaven.Services.Implementation
                 throw new InvalidOperationException("A completion document file is required.");
             }
 
-            if (file.Length > _documentOptions.MaxSizeBytes)
+            // Media contract: photos up to 10 MB (JPEG/PNG/HEIC), videos up to 100 MB
+            // (MP4/MOV). Documents keep the configured VendorDocuments cap.
+            var contentType = ResolveUploadContentType(file);
+            if (contentType == null)
             {
-                throw new InvalidOperationException("The uploaded file exceeds the maximum allowed size.");
+                throw new InvalidOperationException("Only PDF, JPG, PNG, HEIC, MP4, and MOV files are accepted.");
             }
 
-            var contentType = (file.ContentType ?? string.Empty).Trim();
-            if (!AllowedContentTypes.Contains(contentType))
+            // Classify by the resolved type the signature check validates, never by the file name.
+            var kind = WorkOrderMediaContract.ResolveKind(contentType, fileName: null);
+            if (kind == WorkOrderMediaContract.UploadKind.Photo
+                && file.Length > WorkOrderMediaContract.MaxPhotoBytes)
             {
-                throw new InvalidOperationException("Only PDF, JPG, and PNG completion documents are accepted.");
+                throw new InvalidOperationException("Photos must be 10 MB or smaller.");
+            }
+            if (kind == WorkOrderMediaContract.UploadKind.Video
+                && file.Length > WorkOrderMediaContract.MaxVideoBytes)
+            {
+                throw new InvalidOperationException("Videos must be 100 MB or smaller.");
+            }
+            if (kind != WorkOrderMediaContract.UploadKind.Photo
+                && kind != WorkOrderMediaContract.UploadKind.Video
+                && file.Length > _documentOptions.MaxSizeBytes)
+            {
+                throw new InvalidOperationException("The uploaded file exceeds the maximum allowed size.");
             }
 
             var resolvedPurpose = string.IsNullOrWhiteSpace(purpose)
@@ -864,11 +937,21 @@ namespace SeaHaven.Services.Implementation
             await file.CopyToAsync(buffer, cancellationToken);
             var bytes = buffer.ToArray();
 
-            if (!MatchesSignature(contentType, bytes))
+            if (!WorkOrderMediaFileRules.MatchesSignature(contentType, bytes))
             {
                 throw new InvalidOperationException("The uploaded file signature does not match its declared content type.");
             }
 
+            if (kind == WorkOrderMediaContract.UploadKind.Video)
+            {
+                using var content = new MemoryStream(bytes, writable: false);
+                var durationMessage = WorkOrderMediaContract.ValidateVideoDuration(content);
+                if (durationMessage != null)
+                {
+                    throw new InvalidOperationException(durationMessage);
+                }
+            }
+
             var dispatch = await _dispatchData.GetVendorDispatchForMutationAsync(dispatchId, session.Id, cancellationToken);
             if (dispatch == null)
             {
@@ -895,50 +978,80 @@ namespace SeaHaven.Services.Implementation
                         "The completion document could not be replaced.");
                 }
             }
+
             var version = (latest?.Version ?? 0) + 1;
             var storedFileName = $"{dispatchId}_{version}_{Guid.NewGuid():N}{GetSafeExtension(file.FileName)}";
-
-            var now = DateTime.UtcNow;
-            var document = new VendorCompletionDocument
-            {
-                VendorId = session.Id,
-                DispatchId = dispatchId,
-                WorkOrderId = dispatch.WorkOrderId ?? 0,
-                OriginalFileName = Path.GetFileName(file.FileName),
-                StoredFileName = storedFileName,
-                ContentType = contentType,
-                SizeBytes = bytes.Length,
-                ScanStatus = "Pending",
-                ReviewStatus = "Processing",
-                Version = version,
-                ReplacesDocumentId = replacedDocument?.Id,
-                Purpose = resolvedPurpose,
-                CreatedDate = now
-            };
-
-            await _documentData.AddAsync(document, cancellationToken);
-
             var isUpliftEvidence = resolvedPurpose == VendorDocumentPurpose.UpliftEvidence;
-            var fieldName = $"Dispatch {dispatch.DispatchNumber} Completion Document";
 
-            await _dispatchData.StageAuditLogAsync(new WorkOrderAuditLog
+            async Task<VendorCompletionDocument> PersistAsync(CancellationToken ct)
             {
-                WorkOrderId = dispatch.WorkOrderId ?? 0,
-                DispatchId = dispatchId,
-                FieldName = fieldName,
-                OldValue = isUpliftEvidence || replacedDocument == null
-                    ? null
-                    : $"v{replacedDocument.Version}",
-                NewValue = isUpliftEvidence
-                    ? $"evidence {document.OriginalFileName}"
-                    : $"v{version}",
-                Action = isUpliftEvidence
-                    ? "vendor_uplift_evidence_uploaded"
-                    : "vendor_completion_document_uploaded",
-                ActorType = "vendor",
-                CreatedAt = now
-            }, cancellationToken);
-            await _documentData.SaveChangesAsync(cancellationToken);
+                // The 10-photo / 3-video limit is per work order across the dispatcher and
+                // vendor surfaces. A new completion version replaces its predecessor, so that one
+                // does not count against the upload that supersedes it.
+                if (dispatch.WorkOrderId is int workOrderId)
+                {
+                    var excluded = resolvedPurpose == VendorDocumentPurpose.Completion
+                        ? replacedDocument?.Id
+                        : null;
+                    var vendorTypes = await _documentData.ListActiveContentTypesForWorkOrderAsync(
+                        workOrderId, excluded, ct);
+                    var attachmentUrls = await _documentData.ListActiveWorkOrderAttachmentUrlsAsync(
+                        workOrderId, ct);
+                    var countMessage = WorkOrderMediaContract.ValidateCount(kind, attachmentUrls, vendorTypes);
+                    if (countMessage != null)
+                    {
+                        throw new InvalidOperationException(countMessage);
+                    }
+                }
+
+                var now = DateTime.UtcNow;
+                var created = new VendorCompletionDocument
+                {
+                    VendorId = session.Id,
+                    DispatchId = dispatchId,
+                    WorkOrderId = dispatch.WorkOrderId ?? 0,
+                    OriginalFileName = Path.GetFileName(file.FileName),
+                    StoredFileName = storedFileName,
+                    ContentType = contentType,
+                    SizeBytes = bytes.Length,
+                    ScanStatus = "Pending",
+                    ReviewStatus = "Processing",
+                    Version = version,
+                    ReplacesDocumentId = replacedDocument?.Id,
+                    Purpose = resolvedPurpose,
+                    CreatedDate = now
+                };
+
+                await _documentData.AddAsync(created, ct);
+
+                var fieldName = $"Dispatch {dispatch.DispatchNumber} Completion Document";
+
+                await _dispatchData.StageAuditLogAsync(new WorkOrderAuditLog
+                {
+                    WorkOrderId = dispatch.WorkOrderId ?? 0,
+                    DispatchId = dispatchId,
+                    FieldName = fieldName,
+                    OldValue = isUpliftEvidence || replacedDocument == null
+                        ? null
+                        : $"v{replacedDocument.Version}",
+                    NewValue = isUpliftEvidence
+                        ? $"evidence {created.OriginalFileName}"
+                        : $"v{version}",
+                    Action = isUpliftEvidence
+                        ? "vendor_uplift_evidence_uploaded"
+                        : "vendor_completion_document_uploaded",
+                    ActorType = "vendor",
+                    CreatedAt = now
+                }, ct);
+                await _documentData.SaveChangesAsync(ct);
+                return created;
+            }
+
+            // The count and the insert run under the per-work-order mutation lock the dispatcher
+            // media upload also takes, so concurrent uploads cannot both claim the last slot.
+            var document = dispatch.WorkOrderId is int lockedWorkOrderId
+                ? await _upliftData.ExecuteWorkOrderMutationAsync(lockedWorkOrderId, PersistAsync, cancellationToken)
+                : await PersistAsync(cancellationToken);
 
             using var stored = new MemoryStream(bytes);
             await _documentStorage.SaveAsync(session.Id, dispatchId, storedFileName, stored, cancellationToken);
@@ -997,35 +1110,6 @@ namespace SeaHaven.Services.Implementation
             };
         }
 
-        private static bool MatchesSignature(string contentType, byte[] bytes)
-        {
-            if (bytes.Length == 0)
-            {
-                return false;
-            }
-
-            if (contentType.Equals("application/pdf", StringComparison.OrdinalIgnoreCase))
-            {
-                return bytes.Length >= 4
-                    && bytes[0] == 0x25 && bytes[1] == 0x50 && bytes[2] == 0x44 && bytes[3] == 0x46; // %PDF
-            }
-
-            if (contentType.Equals("image/png", StringComparison.OrdinalIgnoreCase))
-            {
-                return bytes.Length >= 8
-                    && bytes[0] == 0x89 && bytes[1] == 0x50 && bytes[2] == 0x4E && bytes[3] == 0x47
-                    && bytes[4] == 0x0D && bytes[5] == 0x0A && bytes[6] == 0x1A && bytes[7] == 0x0A;
-            }
-
-            if (contentType.Equals("image/jpeg", StringComparison.OrdinalIgnoreCase)
-                || contentType.Equals("image/jpg", StringComparison.OrdinalIgnoreCase))
-            {
-                return bytes.Length >= 3 && bytes[0] == 0xFF && bytes[1] == 0xD8 && bytes[2] == 0xFF;
-            }
-
-            return false;
-        }
-
         private static string GetSafeExtension(string fileName)
         {
             var extension = Path.GetExtension(fileName);

SeaHaven.Services/Implementation/WorkOrderMediaService.cs

@@ -16,17 +16,20 @@ namespace SeaHaven.Services.Implementation
         private readonly IWorkOrderDetailDataService _detailData;
         private readonly IWorkOrderAuditService _auditService;
         private readonly IFileStoragePort _fileStorage;
+        private readonly IUpliftDataService _upliftData;
 
         public WorkOrderMediaService(
             IWorkOrderMediaDataService mediaData,
             IWorkOrderDetailDataService detailData,
             IWorkOrderAuditService auditService,
-            IFileStoragePort fileStorage)
+            IFileStoragePort fileStorage,
+            IUpliftDataService upliftData)
         {
             _mediaData = mediaData;
             _detailData = detailData;
             _auditService = auditService;
             _fileStorage = fileStorage;
+            _upliftData = upliftData;
         }
 
         public async Task<IReadOnlyList<WorkOrderMediaFileDto>?> GetMediaAsync(
@@ -153,23 +156,34 @@ namespace SeaHaven.Services.Implementation
                 };
             }
 
-            var attachment = new WorkOrderAttachments
-            {
-                WorkorderId = workOrderId,
-                Attachments = fileUrl,
-                Category = category.HasValue ? resolvedCategory : null,
-                CreatedDate = DateTime.UtcNow,
-                createdby = actorId
-            };
-
-            _mediaData.TrackAttachment(attachment);
-            await _auditService.StageFieldChangedAsync(
+            // Photo/video caps are a work-order aggregate shared with the vendor portal
+            // upload, so the count and the insert run under the per-work-order mutation lock.
+            var attachment = await _upliftData.ExecuteWorkOrderMutationAsync(
                 workOrderId,
-                "MediaCategory",
-                null,
-                FormatMediaAuditValue(null, (attachment.Category ?? WorkOrderMediaCategory.Extra).ToString()),
-                actorId);
-            await SaveMediaAsync(cancellationToken);
+                async ct =>
+                {
+                    await EnsureWithinMediaCountsAsync(workOrderId, fileUrl, ct);
+
+                    var created = new WorkOrderAttachments
+                    {
+                        WorkorderId = workOrderId,
+                        Attachments = fileUrl,
+                        Category = category.HasValue ? resolvedCategory : null,
+                        CreatedDate = DateTime.UtcNow,
+                        createdby = actorId
+                    };
+
+                    _mediaData.TrackAttachment(created);
+                    await _auditService.StageFieldChangedAsync(
+                        workOrderId,
+                        "MediaCategory",
+                        null,
+                        FormatMediaAuditValue(null, (created.Category ?? WorkOrderMediaCategory.Extra).ToString()),
+                        actorId);
+                    await SaveMediaAsync(ct);
+                    return created;
+                },
+                cancellationToken);
 
             return new WorkOrderMediaFileDto
             {
@@ -348,6 +362,29 @@ namespace SeaHaven.Services.Implementation
                 throw new WorkOrderBoardValidationException("ReadOnly", "Work order is read-only in its current status.");
         }
 
+        /// <summary>
+        /// Media contract: at most 10 photos and 3 videos per work order, counted over the
+        /// stored attachment rows plus the work order's current vendor-portal documents. Legacy
+        /// Before/After column slots replace in place and are not counted. Documents have no
+        /// per-work-order count limit.
+        /// </summary>
+        private async Task EnsureWithinMediaCountsAsync(
+            int workOrderId,
+            string fileUrl,
+            CancellationToken cancellationToken)
+        {
+            var kind = WorkOrderMediaContract.ResolveKind(null, fileUrl);
+            if (kind != WorkOrderMediaContract.UploadKind.Photo
+                && kind != WorkOrderMediaContract.UploadKind.Video)
+                return;
+
+            var urls = await _mediaData.ListActiveAttachmentUrlsAsync(workOrderId, cancellationToken);
+            var vendorTypes = await _mediaData.ListActiveVendorMediaContentTypesAsync(workOrderId, cancellationToken);
+            var countMessage = WorkOrderMediaContract.ValidateCount(kind, urls, vendorTypes);
+            if (countMessage != null)
+                throw new WorkOrderBoardValidationException("MediaCountExceeded", countMessage);
+        }
+
         /// <summary>
         /// Account filter for data queries. Null means org-wide (skip ApplyAccountScope).
         /// Call only after EnsureCan* has verified scope is not Missing.
@@ -432,6 +469,7 @@ namespace SeaHaven.Services.Implementation
             {
                 ".jpg" or ".jpeg" => "image/jpeg",
                 ".png" => "image/png",
+                ".heic" => "image/heic",
                 ".mp4" => "video/mp4",
                 ".mov" => "video/quicktime",
                 ".pdf" => "application/pdf",

SeaHavenIndustries.Tests/VideoDurationProbeTests.cs

@@ -0,0 +1,112 @@
+using System.Buffers.Binary;
+using System.Text;
+using SeaHaven.Services.Helpers;
+
+namespace SeaHavenIndustries.Tests;
+
+public class VideoDurationProbeTests
+{
+    internal static byte[] Box(string type, params byte[][] children)
+    {
+        var body = children.SelectMany(child => child).ToArray();
+        var box = new byte[8 + body.Length];
+        BinaryPrimitives.WriteUInt32BigEndian(box, (uint)box.Length);
+        Encoding.ASCII.GetBytes(type).CopyTo(box, 4);
+        body.CopyTo(box, 8);
+        return box;
+    }
+
+    internal static byte[] MovieHeader(uint timescale, ulong duration, bool version1 = false)
+    {
+        var body = new byte[version1 ? 32 : 20];
+        body[0] = version1 ? (byte)1 : (byte)0;
+        if (version1)
+        {
+            BinaryPrimitives.WriteUInt32BigEndian(body.AsSpan(20), timescale);
+            BinaryPrimitives.WriteUInt64BigEndian(body.AsSpan(24), duration);
+        }
+        else
+        {
+            BinaryPrimitives.WriteUInt32BigEndian(body.AsSpan(12), timescale);
+            BinaryPrimitives.WriteUInt32BigEndian(body.AsSpan(16), (uint)duration);
+        }
+        return Box("mvhd", body);
+    }
+
+    /// <summary>A phone-style file: ftyp, a large mdat, then moov at the end (not fast-start).</summary>
+    internal static byte[] Mp4(uint timescale, ulong duration, bool version1 = false, int mediaBytes = 4096)
+    {
+        var ftyp = Box("ftyp", Encoding.ASCII.GetBytes("isom"), new byte[4]);
+        var mdat = Box("mdat", new byte[mediaBytes]);
+        var moov = Box("moov", MovieHeader(timescale, duration, version1));
+        return ftyp.Concat(mdat).Concat(moov).ToArray();
+    }
+
+    [Fact]
+    public void ReadsDurationFromMoovAfterMediaData()
+    {
+        Assert.Equal(95.0, VideoDurationProbe.TryReadDurationSeconds(new MemoryStream(Mp4(600, 57_000))));
+    }
+
+    [Fact]
+    public void ReadsVersionOneMovieHeader()
+    {
+        Assert.Equal(30.5, VideoDurationProbe.TryReadDurationSeconds(
+            new MemoryStream(Mp4(1000, 30_500, version1: true))));
+    }
+
+    [Fact]
+    public void FollowsSixtyFourBitBoxSizes()
+    {
+        var ftyp = Box("ftyp", Encoding.ASCII.GetBytes("qt  "), new byte[4]);
+        var mdatBody = new byte[512];
+        var mdat = new byte[16 + mdatBody.Length];
+        BinaryPrimitives.WriteUInt32BigEndian(mdat, 1);
+        Encoding.ASCII.GetBytes("mdat").CopyTo(mdat, 4);
+        BinaryPrimitives.WriteUInt64BigEndian(mdat.AsSpan(8), (ulong)mdat.Length);
+        var moov = Box("moov", MovieHeader(90_000, 90_000UL * 120));
+        var file = ftyp.Concat(mdat).Concat(moov).ToArray();
+
+        Assert.Equal(120.0, VideoDurationProbe.TryReadDurationSeconds(new MemoryStream(file)));
+    }
+
+    [Theory]
+    [InlineData("no-moov")]
+    [InlineData("truncated")]
+    [InlineData("zero-timescale")]
+    [InlineData("oversized-box")]
+    public void UnreadableStructureReturnsNull(string shape)
+    {
+        var bytes = shape switch
+        {
+            "no-moov" => Box("ftyp", Encoding.ASCII.GetBytes("isom"), new byte[4]).Concat(Box("mdat", new byte[64])).ToArray(),
+            "truncated" => Mp4(600, 57_000)[..^10],
+            "zero-timescale" => Mp4(0, 57_000),
+            _ => Box("ftyp", new byte[8]).Concat(new byte[] { 0x7F, 0xFF, 0xFF, 0xFF, (byte)'m', (byte)'o', (byte)'o', (byte)'v' }).ToArray(),
+        };
+
+        Assert.Null(VideoDurationProbe.TryReadDurationSeconds(new MemoryStream(bytes)));
+    }
+
+    [Fact]
+    public void NonSeekableStreamReturnsNull()
+    {
+        Assert.Null(VideoDurationProbe.TryReadDurationSeconds(new NonSeekableStream(Mp4(600, 57_000))));
+    }
+
+    [Theory]
+    [InlineData(90.0, true)]
+    [InlineData(90.5, false)]
+    public void ContractAllowsUpToNinetySeconds(double seconds, bool allowed)
+    {
+        var message = WorkOrderMediaContract.ValidateVideoDuration(
+            new MemoryStream(Mp4(1000, (ulong)(seconds * 1000))));
+
+        Assert.Equal(allowed ? null : "Videos must be 90 seconds or shorter.", message);
+    }
+
+    private sealed class NonSeekableStream(byte[] bytes) : MemoryStream(bytes)
+    {
+        public override bool CanSeek => false;
+    }
+}

SeaHavenIndustries.Tests/WorkOrderCompletedSelectiveLockTests.cs

@@ -41,7 +41,8 @@ public class WorkOrderCompletedSelectiveLockTests
             new WorkOrderMediaDataService(context),
             new WorkOrderDetailDataService(context),
             audit,
-            new TestFileStoragePort());
+            new TestFileStoragePort(),
+            new UpliftDataService(context));
         return (context, service);
     }
 

SeaHavenIndustries.Tests/WorkOrderMediaConcurrencyRelationalTests.cs

@@ -176,7 +176,8 @@ public class WorkOrderMediaConcurrencyRelationalTests
             new WorkOrderMediaDataService(context),
             new WorkOrderDetailDataService(context),
             audit,
-            new TestFileStoragePort());
+            new TestFileStoragePort(),
+            new UpliftDataService(context));
     }
 
     private static async Task<string> LoadVersionAsync(ApplicationDbContext context, int workOrderId)

SeaHavenIndustries.Tests/WorkOrderPhase6Tests.cs

@@ -1,6 +1,8 @@
 using System.Security.Claims;
 using System.Text;
 using System.IO.Compression;
+using System.Reflection;
+using System.Text.RegularExpressions;
 using Data.SeaHavenIndustries;
 using Data.SeaHavenIndustries.Enums;
 using Microsoft.AspNetCore.Http;
@@ -812,7 +814,8 @@ public class WorkOrderMediaServiceTests
             new WorkOrderMediaDataService(context),
             new WorkOrderDetailDataService(context),
             audit,
-            fileStorage ?? new TestFileStoragePort());
+            fileStorage ?? new TestFileStoragePort(),
+            new UpliftDataService(context));
         return (context, service);
     }
 
@@ -1309,6 +1312,410 @@ public class WorkOrderMediaServiceTests
         Assert.Equal(WorkOrderMediaCategory.Extra, media.Category);
     }
 
+    [Fact]
+    public async Task AddMedia_EleventhPhoto_ThrowsMediaCountExceeded()
+    {
+        var (context, service) = CreateSut();
+        context.workOrders.Add(new WorkOrder
+        {
+            Id = 1,
+            LifecycleStatus = LifecycleStatus.Scheduled,
+            RowVersion = new byte[] { 1, 0, 0, 0, 0, 0, 0, 1 }
+        });
+        for (var i = 0; i < 10; i++)
+        {
+            context.workOrderAttachments.Add(new WorkOrderAttachments
+            {
+                WorkorderId = 1,
+                Attachments = $"https://example.com/photo-{i}.jpg",
+                Category = WorkOrderMediaCategory.Extra
+            });
+        }
+        await context.SaveChangesAsync();
+
+        var ex = await Assert.ThrowsAsync<WorkOrderBoardValidationException>(() =>
+            service.AddMediaAsync(
+                1,
+                null,
+                "https://example.com/photo-10.jpg",
+                AuthenticatedUser(),
+                "actor-1"));
+
+        Assert.Equal("MediaCountExceeded", ex.Code);
+        Assert.Equal("A work order can have at most 10 photos.", ex.Message);
+        Assert.Equal(10, context.workOrderAttachments.Count(a => a.IsDeleted != true));
+    }
+
+    [Fact]
+    public async Task AddMedia_CountsAndInsertsUnderTheWorkOrderMutationLock()
+    {
+        // Distinct id: the mutation gate is process-wide per work order.
+        const int workOrderId = 173_001;
+        var (context, service) = CreateSut();
+        context.workOrders.Add(new WorkOrder
+        {
+            Id = workOrderId,
+            LifecycleStatus = LifecycleStatus.Scheduled,
+            RowVersion = new byte[] { 1, 0, 0, 0, 0, 0, 0, 1 }
+        });
+        for (var i = 0; i < 9; i++)
+        {
+            context.workOrderAttachments.Add(new WorkOrderAttachments
+            {
+                WorkorderId = workOrderId,
+                Attachments = $"https://example.com/photo-{i}.jpg",
+                Category = WorkOrderMediaCategory.Extra
+            });
+        }
+        await context.SaveChangesAsync();
+
+        var held = new TaskCompletionSource(TaskCreationOptions.RunContinuationsAsynchronously);
+        var release = new TaskCompletionSource(TaskCreationOptions.RunContinuationsAsynchronously);
+        var holder = new UpliftDataService(context).ExecuteWorkOrderMutationAsync(
+            workOrderId,
+            async _ =>
+            {
+                held.SetResult();
+                await release.Task;
+                return 0;
+            },
+            CancellationToken.None);
+        await held.Task;
+
+        var upload = service.AddMediaAsync(
+            workOrderId,
+            null,
+            "https://example.com/photo-9.jpg",
+            AuthenticatedUser(),
+            "actor-1");
+        await Task.Delay(200);
+
+        Assert.False(upload.IsCompleted);
+        Assert.Equal(9, context.workOrderAttachments.Count(a => a.WorkorderId == workOrderId && a.IsDeleted != true));
+
+        release.SetResult();
+        await holder;
+        await upload;
+
+        Assert.Equal(10, context.workOrderAttachments.Count(a => a.WorkorderId == workOrderId && a.IsDeleted != true));
+    }
+
+    [Fact]
+    public async Task AddMedia_FourthVideo_CountsStoredPhoneFileUrls()
+    {
+        // Same URL shape FileStorageAdapter.SaveFileAsync returns for an iPhone upload.
+        static string StoredUrl(string name) =>
+            $"https://api.example.com/Assets/Documents/{Guid.NewGuid()}_{name}";
+
+        var (context, service) = CreateSut();
+        context.workOrders.Add(new WorkOrder
+        {
+            Id = 1,
+            LifecycleStatus = LifecycleStatus.Scheduled,
+            RowVersion = new byte[] { 1, 0, 0, 0, 0, 0, 0, 1 }
+        });
+        foreach (var name in new[] { "IMG_0001.MOV", "IMG_0002.mov", "clip.MP4" })
+        {
+            context.workOrderAttachments.Add(new WorkOrderAttachments
+            {
+                WorkorderId = 1,
+                Attachments = StoredUrl(name),
+                Category = WorkOrderMediaCategory.Extra
+            });
+        }
+        await context.SaveChangesAsync();
+
+        var ex = await Assert.ThrowsAsync<WorkOrderBoardValidationException>(() =>
+            service.AddMediaAsync(
+                1,
+                null,
+                StoredUrl("IMG_0004.MOV"),
+                AuthenticatedUser(),
+                "actor-1"));
+
+        Assert.Equal("MediaCountExceeded", ex.Code);
+        Assert.Equal("A work order can have at most 3 videos.", ex.Message);
+    }
+
+    [Fact]
+    public async Task AddMedia_FourthVideo_CountsVendorPortalVideos()
+    {
+        var (context, service) = CreateSut();
+        context.workOrders.Add(new WorkOrder
+        {
+            Id = 1,
+            LifecycleStatus = LifecycleStatus.Scheduled,
+            RowVersion = new byte[] { 1, 0, 0, 0, 0, 0, 0, 1 }
+        });
+        foreach (var name in new[] { "IMG_0001.MOV", "IMG_0002.MOV" })
+        {
+            context.workOrderAttachments.Add(new WorkOrderAttachments
+            {
+                WorkorderId = 1,
+                Attachments = $"https://api.example.com/Assets/Documents/{Guid.NewGuid()}_{name}",
+                Category = WorkOrderMediaCategory.Extra
+            });
+        }
+        // Vendor v1 video was replaced by v2 (also a video): only v2 is current.
+        context.VendorCompletionDocuments.Add(new VendorCompletionDocument
+        {
+            Id = 50,
+            WorkOrderId = 1,
+            DispatchId = 7,
+            VendorId = 3,
+            Version = 1,
+            ContentType = "video/mp4",
+            Purpose = "Completion"
+        });
+        context.VendorCompletionDocuments.Add(new VendorCompletionDocument
+        {
+            Id = 51,
+            WorkOrderId = 1,
+            DispatchId = 7,
+            VendorId = 3,
+            Version = 2,
+            ContentType = "video/quicktime",
+            Purpose = "Completion",
+            ReplacesDocumentId = 50
+        });
+        // Another work order's vendor video never counts here.
+        context.VendorCompletionDocuments.Add(new VendorCompletionDocument
+        {
+            Id = 60,
+            WorkOrderId = 2,
+            DispatchId = 8,
+            VendorId = 3,
+            Version = 1,
+            ContentType = "video/mp4",
+            Purpose = "Completion"
+        });
+        await context.SaveChangesAsync();
+
+        var ex = await Assert.ThrowsAsync<WorkOrderBoardValidationException>(() =>
+            service.AddMediaAsync(
+                1,
+                null,
+                "https://api.example.com/Assets/Documents/x_IMG_0004.MOV",
+                AuthenticatedUser(),
+                "actor-1"));
+
+        Assert.Equal("MediaCountExceeded", ex.Code);
+        Assert.Equal("A work order can have at most 3 videos.", ex.Message);
+        Assert.Equal(2, context.workOrderAttachments.Count());
+    }
+
+    [Fact]
+    public async Task AddMedia_CrossAccount_FullWorkOrder_ThrowsNotFoundNotCount()
+    {
+        var (context, service) = CreateSut();
+        context.workOrders.Add(new WorkOrder
+        {
+            Id = 1,
+            AccountId = 20,
+            LifecycleStatus = LifecycleStatus.Scheduled,
+            RowVersion = new byte[] { 1, 0, 0, 0, 0, 0, 0, 1 }
+        });
+        for (var i = 0; i < 10; i++)
+        {
+            context.workOrderAttachments.Add(new WorkOrderAttachments
+            {
+                WorkorderId = 1,
+                Attachments = $"https://example.com/photo-{i}.jpg",
+                Category = WorkOrderMediaCategory.Extra
+            });
+        }
+        await context.SaveChangesAsync();
+
+        var ex = await Assert.ThrowsAsync<WorkOrderBoardValidationException>(() =>
+            service.AddMediaAsync(
+                1,
+                null,
+                "https://example.com/photo-10.jpg",
+                AuthenticatedUser(accountId: 10),
+                "actor-1"));
+
+        // Another account must not learn the work order exists or how full it is.
+        Assert.Equal("NotFound", ex.Code);
+        Assert.Equal(10, context.workOrderAttachments.Count(a => a.IsDeleted != true));
+    }
+
+    [Fact]
+    public async Task AddMedia_TenthPhoto_Succeeds()
+    {
+        var (context, service) = CreateSut();
+        context.workOrders.Add(new WorkOrder
+        {
+            Id = 1,
+            LifecycleStatus = LifecycleStatus.Scheduled,
+            RowVersion = new byte[] { 1, 0, 0, 0, 0, 0, 0, 1 }
+        });
+        for (var i = 0; i < 9; i++)
+        {
+            context.workOrderAttachments.Add(new WorkOrderAttachments
+            {
+                WorkorderId = 1,
+                Attachments = $"https://example.com/photo-{i}.jpg",
+                Category = WorkOrderMediaCategory.Extra
+            });
+        }
+        await context.SaveChangesAsync();
+
+        var media = await service.AddMediaAsync(
+            1,
+            null,
+            "https://example.com/photo-9.jpg",
+            AuthenticatedUser(),
+            "actor-1");
+
+        Assert.True(media.Id > 0);
+    }
+
+    [Fact]
+    public async Task AddMedia_FourthVideo_ThrowsMediaCountExceeded()
+    {
+        var (context, service) = CreateSut();
+        context.workOrders.Add(new WorkOrder
+        {
+            Id = 1,
+            LifecycleStatus = LifecycleStatus.Scheduled,
+            RowVersion = new byte[] { 1, 0, 0, 0, 0, 0, 0, 1 }
+        });
+        context.workOrderAttachments.Add(new WorkOrderAttachments
+        {
+            WorkorderId = 1,
+            Attachments = "https://example.com/clip-a.mp4",
+            Category = WorkOrderMediaCategory.Extra
+        });
+        context.workOrderAttachments.Add(new WorkOrderAttachments
+        {
+            WorkorderId = 1,
+            Attachments = "https://example.com/clip-b.mov",
+            Category = WorkOrderMediaCategory.Extra
+        });
+        context.workOrderAttachments.Add(new WorkOrderAttachments
+        {
+            WorkorderId = 1,
+            Attachments = "https://example.com/clip-c.mp4",
+            Category = WorkOrderMediaCategory.Extra
+        });
+        await context.SaveChangesAsync();
+
+        var ex = await Assert.ThrowsAsync<WorkOrderBoardValidationException>(() =>
+            service.AddMediaAsync(
+                1,
+                null,
+                "https://example.com/clip-d.mov",
+                AuthenticatedUser(),
+                "actor-1"));
+
+        Assert.Equal("MediaCountExceeded", ex.Code);
+        Assert.Equal("A work order can have at most 3 videos.", ex.Message);
+    }
+
+    [Fact]
+    public async Task AddMedia_ThirdVideo_Succeeds()
+    {
+        var (context, service) = CreateSut();
+        context.workOrders.Add(new WorkOrder
+        {
+            Id = 1,
+            LifecycleStatus = LifecycleStatus.Scheduled,
+            RowVersion = new byte[] { 1, 0, 0, 0, 0, 0, 0, 1 }
+        });
+        context.workOrderAttachments.Add(new WorkOrderAttachments
+        {
+            WorkorderId = 1,
+            Attachments = "https://example.com/clip-a.mp4",
+            Category = WorkOrderMediaCategory.Extra
+        });
+        context.workOrderAttachments.Add(new WorkOrderAttachments
+        {
+            WorkorderId = 1,
+            Attachments = "https://example.com/clip-b.mov",
+            Category = WorkOrderMediaCategory.Extra
+        });
+        await context.SaveChangesAsync();
+
+        var media = await service.AddMediaAsync(
+            1,
+            null,
+            "https://example.com/clip-c.mp4",
+            AuthenticatedUser(),
+            "actor-1");
+
+        Assert.True(media.Id > 0);
+    }
+
+    [Fact]
+    public async Task AddMedia_DeletedPhoto_DoesNotConsumePhotoCount()
+    {
+        var (context, service) = CreateSut();
+        context.workOrders.Add(new WorkOrder
+        {
+            Id = 1,
+            LifecycleStatus = LifecycleStatus.Scheduled,
+            RowVersion = new byte[] { 1, 0, 0, 0, 0, 0, 0, 1 }
+        });
+        for (var i = 0; i < 10; i++)
+        {
+            context.workOrderAttachments.Add(new WorkOrderAttachments
+            {
+                WorkorderId = 1,
+                Attachments = $"https://example.com/photo-{i}.jpg",
+                Category = WorkOrderMediaCategory.Extra,
+                IsDeleted = i == 0
+            });
+        }
+        await context.SaveChangesAsync();
+
+        var media = await service.AddMediaAsync(
+            1,
+            null,
+            "https://example.com/photo-new.jpg",
+            AuthenticatedUser(),
+            "actor-1");
+
+        Assert.True(media.Id > 0);
+    }
+
+    [Fact]
+    public async Task AddMedia_DocumentsDoNotConsumePhotoOrVideoCounts()
+    {
+        var (context, service) = CreateSut();
+        context.workOrders.Add(new WorkOrder
+        {
+            Id = 1,
+            LifecycleStatus = LifecycleStatus.Scheduled,
+            RowVersion = new byte[] { 1, 0, 0, 0, 0, 0, 0, 1 }
+        });
+        for (var i = 0; i < 5; i++)
+        {
+            context.workOrderAttachments.Add(new WorkOrderAttachments
+            {
+                WorkorderId = 1,
+                Attachments = $"https://example.com/report-{i}.pdf",
+                Category = WorkOrderMediaCategory.Extra
+            });
+        }
+        await context.SaveChangesAsync();
+
+        var photo = await service.AddMediaAsync(
+            1,
+            null,
+            "https://example.com/photo.jpg",
+            AuthenticatedUser(),
+            "actor-1");
+        var video = await service.AddMediaAsync(
+            1,
+            null,
+            "https://example.com/clip.mp4",
+            AuthenticatedUser(),
+            "actor-1");
+
+        Assert.True(photo.Id > 0);
+        Assert.True(video.Id > 0);
+    }
+
     [Fact]
     public async Task DeleteMedia_Technician_ThrowsForbidden()
     {
@@ -1968,6 +2375,32 @@ public class WorkOrderMediaFileRulesTests
         return stream.ToArray();
     }
 
+    [Fact]
+    public void EnsureAllowed_RejectionMessage_NamesEveryAllowedType()
+    {
+        const BindingFlags privateStatic = BindingFlags.NonPublic | BindingFlags.Static;
+        var allowedTypes = (HashSet<string>?)typeof(WorkOrderMediaFileRules)
+            .GetField("AllowedContentTypes", privateStatic)?.GetValue(null);
+        var extensionsByType = (Dictionary<string, HashSet<string>>?)typeof(WorkOrderMediaFileRules)
+            .GetField("ExtensionsByContentType", privateStatic)?.GetValue(null);
+        Assert.NotNull(allowedTypes);
+        Assert.NotNull(extensionsByType);
+        Assert.NotEmpty(allowedTypes);
+
+        var ex = Assert.Throws<WorkOrderBoardValidationException>(
+            () => WorkOrderMediaFileRules.EnsureAllowed(FormFile(Encoding.UTF8.GetBytes("plain text"), "notes.txt", "text/plain")));
+
+        foreach (var contentType in allowedTypes)
+        {
+            var canonical = contentType.Equals("image/jpg", StringComparison.OrdinalIgnoreCase) ? "image/jpeg" : contentType;
+            Assert.True(extensionsByType.TryGetValue(canonical, out var extensions), $"No extensions mapped for {contentType}.");
+            var labels = extensions.Select(extension => extension.TrimStart('.').ToUpperInvariant()).ToList();
+            Assert.True(
+                labels.Any(label => Regex.IsMatch(ex.Message, $@"\b{Regex.Escape(label)}\b")),
+                $"Rejection message does not name {contentType} ({string.Join("/", labels)}): {ex.Message}");
+        }
+    }
+
     [Fact]
     public void IsAllowed_ValidJpeg_ReturnsTrue()
     {

scripts/check_app_terraform_isolation.py

@@ -26,7 +26,7 @@ def is_app_path(path: str) -> bool:
     normalized = path.replace("\\", "/")
     if normalized in APP_SCRIPT_NAMES:
         return True
-    if normalized.startswith(".ebextensions/"):
+    if normalized.startswith((".ebextensions/", ".platform/")):
         return True
     return normalized.endswith(APP_SUFFIXES)
 

scripts/package-elastic-beanstalk.sh

@@ -8,6 +8,7 @@
 #   ./                          published Api.SeaHavenIndustries (self-contained, linux-x64)
 #   ./efbundle                  self-contained EF Core 8.0.8 migrations bundle (linux-x64, +x)
 #   ./.ebextensions/*           leader-only migration container command
+#   ./.platform/nginx/conf.d/*  nginx proxy overrides (upload body size)
 #
 # The bundle reads ConnectionStrings__DefaultConnection from the runtime
 # environment (Elastic Beanstalk property). No connection string or secret is
@@ -137,6 +138,10 @@ log "copy .ebextensions into bundle root"
 mkdir -p "$STAGING_DIR/.ebextensions"
 cp -R .ebextensions/. "$STAGING_DIR/.ebextensions/"
 
+log "copy .platform (nginx proxy overrides) into bundle root"
+mkdir -p "$STAGING_DIR/.platform"
+cp -R .platform/. "$STAGING_DIR/.platform/"
+
 log "verify no committed secret placeholders survived publish"
 if grep -rIEl -- 'Server=.*;.*Password=|AccountKey=|aws_secret|AKIA[0-9A-Z]{16}' "$STAGING_DIR" 2>/dev/null; then
   die "potential secret detected in publish output; refusing to package."

scripts/test_check_app_terraform_isolation.py

@@ -54,6 +54,17 @@ class IsolationTests(unittest.TestCase):
         self.assertEqual(terraform_files, ["terraform/live/dev/main.tf"])
         self.assertTrue(any(path.endswith(".cs") for path in app_files))
 
+    def test_platform_proxy_config_is_app_side(self) -> None:
+        violation = isolation_violation(
+            [
+                "terraform/live/dev/main.tf",
+                ".platform/nginx/conf.d/01_upload_body_size.conf",
+            ]
+        )
+        self.assertIsNotNone(violation)
+        _, app_files = violation or ([], [])
+        self.assertEqual(app_files, [".platform/nginx/conf.d/01_upload_body_size.conf"])
+
 
 if __name__ == "__main__":
     unittest.main()

scripts/validate-elastic-beanstalk-bundle.sh

@@ -15,13 +15,15 @@ die() {
 
 contents_file="$(mktemp)"
 webhook_file="$(mktemp)"
-trap 'rm -f "$contents_file" "$webhook_file"' EXIT
+nginx_file="$(mktemp)"
+trap 'rm -f "$contents_file" "$webhook_file" "$nginx_file"' EXIT
 
 unzip -tq "$BUNDLE"
 unzip -Z1 "$BUNDLE" > "$contents_file"
 grep -Fxq "efbundle" "$contents_file"
 grep -Fxq ".ebextensions/01_migrations.config" "$contents_file"
 grep -Fxq ".ebextensions/02_webhook_config.config" "$contents_file"
+grep -Fxq ".platform/nginx/conf.d/01_upload_body_size.conf" "$contents_file"
 
 unzip -p "$BUNDLE" .ebextensions/02_webhook_config.config > "$webhook_file"
 grep -Fxq '    WorkOrderWebhook__Enabled: "true"' "$webhook_file"
@@ -30,5 +32,9 @@ grep -Fxq \
   '    WorkOrderWebhook__SecretId: arn:aws:secretsmanager:us-east-1:011934824531:secret:workorder-ingest/shoc-webhook-hmac-puYTcB' \
   "$webhook_file"
 
+# Without this override the platform nginx caps request bodies at 1 MB.
+unzip -p "$BUNDLE" .platform/nginx/conf.d/01_upload_body_size.conf > "$nginx_file"
+grep -Fxq 'client_max_body_size 120M;' "$nginx_file"
+
 printf 'PASS: Elastic Beanstalk bundle contract (%s bytes)\n' \
   "$(wc -c < "$BUNDLE" | tr -d ' ')"