From 13ffbe911a3b6c96e54481c3996482e79d16d6df Mon Sep 17 00:00:00 2001
From: Matt Gibson <mgibson@bitwarden.com>
Date: Mon, 29 Mar 2021 09:45:04 -0500
Subject: [PATCH] Send azure upload (#1334)

* Add direct upload api endpoints

* Create azure upload service

* Update max file size

* Update send file upload test

* Move internationalization string to correct document

* Allow for one shot blob uploads

* Remove unused helper

* Use FileUploadService

Fallback to legacy method on old server implementations.
---
 src/App/Pages/Send/SendAddEditPage.xaml       |   4 +-
 .../Pages/Send/SendAddEditPageViewModel.cs    |   2 +-
 src/App/Resources/AppResources.resx           |   3 +
 src/Core/Abstractions/IApiService.cs          |   4 +
 .../Abstractions/IAzureFileUpoadService.cs    |  10 +
 src/Core/Abstractions/IFileUploadService.cs   |   9 +
 src/Core/Enums/FileUploadType.cs              |   9 +
 .../Response/SendFileUploadDataResponse.cs    |  12 ++
 src/Core/Services/ApiService.cs               |  10 +
 src/Core/Services/AzureFileUploadService.cs   | 196 ++++++++++++++++++
 .../Services/BitwardenFileUploadService.cs    |  26 +++
 src/Core/Services/FileUploadService.cs        |  51 +++++
 src/Core/Services/SendService.cs              |  41 +++-
 src/Core/Utilities/CoreHelpers.cs             |   2 +-
 src/Core/Utilities/ServiceContainer.cs        |   5 +-
 test/Core.Test/Services/SendServiceTests.cs   |  56 ++---
 16 files changed, 400 insertions(+), 40 deletions(-)
 create mode 100644 src/Core/Abstractions/IAzureFileUpoadService.cs
 create mode 100644 src/Core/Abstractions/IFileUploadService.cs
 create mode 100644 src/Core/Enums/FileUploadType.cs
 create mode 100644 src/Core/Models/Response/SendFileUploadDataResponse.cs
 create mode 100644 src/Core/Services/AzureFileUploadService.cs
 create mode 100644 src/Core/Services/BitwardenFileUploadService.cs
 create mode 100644 src/Core/Services/FileUploadService.cs

diff --git a/src/App/Pages/Send/SendAddEditPage.xaml b/src/App/Pages/Send/SendAddEditPage.xaml
index 1ff2b8f77..963312d6b 100644
--- a/src/App/Pages/Send/SendAddEditPage.xaml
+++ b/src/App/Pages/Send/SendAddEditPage.xaml
@@ -215,7 +215,7 @@
                                     Clicked="ChooseFile_Clicked" />
                                 <Label
                                     Margin="0, 5, 0, 0"
-                                    Text="{u:I18n MaxFileSize}"
+                                    Text="{u:I18n MaxFileSizeSend}"
                                     StyleClass="text-sm, text-muted"
                                     HorizontalOptions="FillAndExpand"
                                     HorizontalTextAlignment="Center" />
@@ -513,4 +513,4 @@
         </ResourceDictionary>
     </ContentPage.Resources>
 
-</pages:BaseContentPage>
\ No newline at end of file
+</pages:BaseContentPage>
diff --git a/src/App/Pages/Send/SendAddEditPageViewModel.cs b/src/App/Pages/Send/SendAddEditPageViewModel.cs
index b729d29ce..e3624779e 100644
--- a/src/App/Pages/Send/SendAddEditPageViewModel.cs
+++ b/src/App/Pages/Send/SendAddEditPageViewModel.cs
@@ -327,7 +327,7 @@ namespace Bit.App.Pages
                             AppResources.AnErrorHasOccurred);
                         return false;
                     }
-                    if (FileData.Length > 104857600) // 100 MB
+                    if (FileData.Length > 524288000) // 500 MB
                     {
                         await _platformUtilsService.ShowDialogAsync(AppResources.MaxFileSize,
                             AppResources.AnErrorHasOccurred);
diff --git a/src/App/Resources/AppResources.resx b/src/App/Resources/AppResources.resx
index 326fa92c1..806ab4c2f 100644
--- a/src/App/Resources/AppResources.resx
+++ b/src/App/Resources/AppResources.resx
@@ -927,6 +927,9 @@
   </data>
   <data name="MaxFileSize" xml:space="preserve">
     <value>Maximum file size is 100 MB.</value>
+  </data>
+    <data name="MaxFileSizeSend" xml:space="preserve">
+    <value>Maximum file size is 500 MB.</value>
   </data>
   <data name="UpdateKey" xml:space="preserve">
     <value>You cannot use this feature until you update your encryption key.</value>
diff --git a/src/Core/Abstractions/IApiService.cs b/src/Core/Abstractions/IApiService.cs
index 0f79493bd..4edeba2fd 100644
--- a/src/Core/Abstractions/IApiService.cs
+++ b/src/Core/Abstractions/IApiService.cs
@@ -56,7 +56,11 @@ namespace Bit.Core.Abstractions
 
         Task<SendResponse> GetSendAsync(string id);
         Task<SendResponse> PostSendAsync(SendRequest request);
+        Task<SendFileUploadDataResponse> PostFileTypeSendAsync(SendRequest request);
+        Task PostSendFileAsync(string sendId, string fileId, MultipartFormDataContent data);
+        [Obsolete("Mar 25 2021: This method has been deprecated in favor of direct uploads. This method still exists for backward compatibility with old server versions.")]
         Task<SendResponse> PostSendFileAsync(MultipartFormDataContent data);
+        Task<SendFileUploadDataResponse> RenewFileUploadUrlAsync(string sendId, string fileId);
         Task<SendResponse> PutSendAsync(string id, SendRequest request);
         Task<SendResponse> PutSendRemovePasswordAsync(string id);
         Task DeleteSendAsync(string id);
diff --git a/src/Core/Abstractions/IAzureFileUpoadService.cs b/src/Core/Abstractions/IAzureFileUpoadService.cs
new file mode 100644
index 000000000..fe38ffb4f
--- /dev/null
+++ b/src/Core/Abstractions/IAzureFileUpoadService.cs
@@ -0,0 +1,10 @@
+using System;
+using System.Threading.Tasks;
+
+namespace Bit.Core.Abstractions
+{
+    public interface IAzureFileUploadService
+    {
+        Task Upload(string uri, byte[] data, Func<Task<string>> renewalCallback);
+    }
+}
diff --git a/src/Core/Abstractions/IFileUploadService.cs b/src/Core/Abstractions/IFileUploadService.cs
new file mode 100644
index 000000000..b0da4e170
--- /dev/null
+++ b/src/Core/Abstractions/IFileUploadService.cs
@@ -0,0 +1,9 @@
+using System.Threading.Tasks;
+using Bit.Core.Models.Domain;
+using Bit.Core.Models.Response;
+
+namespace Bit.Core.Abstractions {
+    public interface IFileUploadService {
+        Task UploadSendFileAsync(SendFileUploadDataResponse uploadData, CipherString fileName, byte[] encryptedFileData);
+    }
+}
diff --git a/src/Core/Enums/FileUploadType.cs b/src/Core/Enums/FileUploadType.cs
new file mode 100644
index 000000000..8aeb51072
--- /dev/null
+++ b/src/Core/Enums/FileUploadType.cs
@@ -0,0 +1,9 @@
+using System;
+namespace Bit.Core.Enums
+{
+    public enum FileUploadType
+    {
+        Direct = 0,
+        Azure = 1,
+    }
+}
diff --git a/src/Core/Models/Response/SendFileUploadDataResponse.cs b/src/Core/Models/Response/SendFileUploadDataResponse.cs
new file mode 100644
index 000000000..8ea79ae0e
--- /dev/null
+++ b/src/Core/Models/Response/SendFileUploadDataResponse.cs
@@ -0,0 +1,12 @@
+using System;
+using Bit.Core.Enums;
+
+namespace Bit.Core.Models.Response
+{
+    public class SendFileUploadDataResponse
+    {
+        public string Url { get; set; }
+        public FileUploadType FileUploadType { get; set; }
+        public SendResponse SendResponse { get; set; }
+    }
+}
diff --git a/src/Core/Services/ApiService.cs b/src/Core/Services/ApiService.cs
index 8f5245593..f0ea50bbd 100644
--- a/src/Core/Services/ApiService.cs
+++ b/src/Core/Services/ApiService.cs
@@ -223,9 +223,19 @@ namespace Bit.Core.Services
         public Task<SendResponse> PostSendAsync(SendRequest request) =>
             SendAsync<SendRequest, SendResponse>(HttpMethod.Post, "/sends", request, true, true);
 
+        public Task<SendFileUploadDataResponse> PostFileTypeSendAsync(SendRequest request) =>
+            SendAsync<SendRequest, SendFileUploadDataResponse>(HttpMethod.Post, "/sends/file/v2", request, true, true);
+
+        public Task PostSendFileAsync(string sendId, string fileId, MultipartFormDataContent data) =>
+            SendAsync<MultipartFormDataContent, object>(HttpMethod.Post, $"/sends/{sendId}/file/{fileId}", data, true, false);
+
+        [Obsolete("Mar 25 2021: This method has been deprecated in favor of direct uploads. This method still exists for backward compatibility with old server versions.")]
         public Task<SendResponse> PostSendFileAsync(MultipartFormDataContent data) =>
             SendAsync<MultipartFormDataContent, SendResponse>(HttpMethod.Post, "/sends/file", data, true, true);
 
+        public Task<SendFileUploadDataResponse> RenewFileUploadUrlAsync(string sendId, string fileId) =>
+            SendAsync<object, SendFileUploadDataResponse>(HttpMethod.Get, $"/sends/{sendId}/file/{fileId}", null, true, true);
+
         public Task<SendResponse> PutSendAsync(string id, SendRequest request) =>
             SendAsync<SendRequest, SendResponse>(HttpMethod.Put, $"/sends/{id}", request, true, true);
 
diff --git a/src/Core/Services/AzureFileUploadService.cs b/src/Core/Services/AzureFileUploadService.cs
new file mode 100644
index 000000000..5b77de31f
--- /dev/null
+++ b/src/Core/Services/AzureFileUploadService.cs
@@ -0,0 +1,196 @@
+using System;
+using System.Collections.Generic;
+using System.Linq;
+using System.Net;
+using System.Net.Http;
+using System.Net.Http.Headers;
+using System.Text;
+using System.Threading.Tasks;
+using System.Web;
+using Bit.Core.Abstractions;
+using Bit.Core.Utilities;
+
+namespace Bit.Core.Services
+{
+    public class AzureFileUploadService : IAzureFileUploadService
+    {
+        private const long MAX_SINGLE_BLOB_UPLOAD_SIZE = 256 * 1024 * 1024; // 256 MiB
+        private const int MAX_BLOCKS_PER_BLOB = 50000;
+        private const decimal MAX_MOBILE_BLOCK_SIZE = 5 * 1024 * 1024; // 5 MB
+
+        private readonly HttpClient _httpClient = new HttpClient();
+
+        public AzureFileUploadService()
+        {
+            _httpClient.DefaultRequestHeaders.CacheControl = new CacheControlHeaderValue()
+            {
+                NoCache = true,
+            };
+        }
+
+        public async Task Upload(string uri, byte[] data, Func<Task<string>> renewalCallback)
+        {
+            if (data.Length <= MAX_SINGLE_BLOB_UPLOAD_SIZE)
+            {
+                await AzureUploadBlob(uri, data);
+            }
+            else
+            {
+                await AzureUploadBlocks(uri, data, renewalCallback);
+            }
+        }
+
+        private async Task AzureUploadBlob(string uri, byte[] data)
+        {
+            using (var requestMessage = new HttpRequestMessage())
+            {
+                var uriBuilder = new UriBuilder(uri);
+                var paramValues = HttpUtility.ParseQueryString(uriBuilder.Query);
+
+                requestMessage.Headers.Add("x-ms-date", DateTime.UtcNow.ToString("R"));
+                requestMessage.Headers.Add("x-ms-version", paramValues["sv"]);
+                requestMessage.Headers.Add("x-ms-blob-type", "BlockBlob");
+
+                requestMessage.Content = new ByteArrayContent(data);
+                requestMessage.Version = new Version(1, 0);
+                requestMessage.Method = HttpMethod.Put;
+                requestMessage.RequestUri = uriBuilder.Uri;
+
+                var blobResponse = await _httpClient.SendAsync(requestMessage);
+
+                if (blobResponse.StatusCode != HttpStatusCode.Created)
+                {
+                    throw new Exception("Failed to create Azure blob");
+                }
+            }
+        }
+
+        private async Task AzureUploadBlocks(string uri, byte[] data, Func<Task<string>> renewalFunc)
+        {
+            _httpClient.Timeout = TimeSpan.FromHours(3);
+            var baseParams = HttpUtility.ParseQueryString(CoreHelpers.GetUri(uri).Query);
+            var blockSize = MaxBlockSize(baseParams["sv"]);
+            var blockIndex = 0;
+            var numBlocks = Math.Ceiling((decimal)data.Length / blockSize);
+            var blocksStaged = new List<string>();
+
+            if (numBlocks > MAX_BLOCKS_PER_BLOB)
+            {
+                throw new Exception($"Cannot upload file, exceeds maximum size of {blockSize * MAX_BLOCKS_PER_BLOB}");
+            }
+
+                while (blockIndex < numBlocks)
+                {
+                    uri = await RenewUriIfNecessary(uri, renewalFunc);
+                    var blockUriBuilder = new UriBuilder(uri);
+                    var blockId = EncodeBlockId(blockIndex);
+                    var blockParams = HttpUtility.ParseQueryString(blockUriBuilder.Query);
+                    blockParams.Add("comp", "block");
+                    blockParams.Add("blockid", blockId);
+                    blockUriBuilder.Query = blockParams.ToString();
+
+                    using (var requestMessage = new HttpRequestMessage())
+                    {
+                        requestMessage.Headers.Add("x-ms-date", DateTime.UtcNow.ToString("R"));
+                        requestMessage.Headers.Add("x-ms-version", baseParams["sv"]);
+                        requestMessage.Headers.Add("x-ms-blob-type", "BlockBlob");
+
+                        requestMessage.Content = new ByteArrayContent(data.Skip(blockIndex * blockSize).Take(blockSize).ToArray());
+                        requestMessage.Version = new Version(1, 0);
+                        requestMessage.Method = HttpMethod.Put;
+                        requestMessage.RequestUri = blockUriBuilder.Uri;
+
+                        var blockResponse = await _httpClient.SendAsync(requestMessage);
+
+                        if (blockResponse.StatusCode != HttpStatusCode.Created)
+                        {
+                            throw new Exception("Failed to create Azure block");
+                        }
+                    }
+
+                    blocksStaged.Add(blockId);
+                    blockIndex++;
+                }
+
+                using (var requestMessage = new HttpRequestMessage())
+                {
+                    uri = await RenewUriIfNecessary(uri, renewalFunc);
+                    var blockListXml = GenerateBlockListXml(blocksStaged);
+                    var blockListUriBuilder = new UriBuilder(uri);
+                    var blockListParams = HttpUtility.ParseQueryString(blockListUriBuilder.Query);
+                    blockListParams.Add("comp", "blocklist");
+                    blockListUriBuilder.Query = blockListParams.ToString();
+
+                    requestMessage.Headers.Add("x-ms-date", DateTime.UtcNow.ToString("R"));
+                    requestMessage.Headers.Add("x-ms-version", baseParams["sv"]);
+
+                    requestMessage.Content = new StringContent(blockListXml);
+                    requestMessage.Version = new Version(1, 0);
+                    requestMessage.Method = HttpMethod.Put;
+                    requestMessage.RequestUri = blockListUriBuilder.Uri;
+
+                    var blockListResponse = await _httpClient.SendAsync(requestMessage);
+
+                    if (blockListResponse.StatusCode != HttpStatusCode.Created)
+                    {
+                        throw new Exception("Failed to PUT Azure block list");
+                    }
+                }
+        }
+
+        private async Task<string> RenewUriIfNecessary(string uri, Func<Task<string>> renewalFunc)
+        {
+            var uriParams = HttpUtility.ParseQueryString(CoreHelpers.GetUri(uri).Query);
+
+            if (DateTime.TryParse(uriParams.Get("se") ?? "", out DateTime expiry) && expiry < DateTime.UtcNow.AddSeconds(1))
+            {
+                return await renewalFunc();
+            }
+            return uri;
+        }
+
+        private string GenerateBlockListXml(List<string> blocksStaged)
+        {
+            var xml = new StringBuilder("<?xml version=\"1.0\" encoding=\"utf-8\"?><BlockList>");
+            foreach(var blockId in blocksStaged)
+            {
+                xml.Append($"<Latest>{blockId}</Latest>");
+            }
+            xml.Append("</BlockList>");
+            return xml.ToString();
+        }
+
+        private string EncodeBlockId(int index)
+        {
+            // Encoded blockId max size is 64, so pre-encoding max size is 48
+            var paddedString = index.ToString("D48");
+            return Convert.ToBase64String(Encoding.UTF8.GetBytes(paddedString));
+        }
+
+        private int MaxBlockSize(string version)
+        {
+            long maxSize = 4194304L; // 4 MiB
+            if (CompareAzureVersions(version, "2019-12-12") >= 0)
+            {
+                maxSize = 4194304000L; // 4000 MiB
+            }
+            else if (CompareAzureVersions(version, "2016-05-31") >= 0)
+            {
+                maxSize = 104857600L; // 100 MiB
+            }
+
+            return maxSize > MAX_MOBILE_BLOCK_SIZE ? (int)MAX_MOBILE_BLOCK_SIZE : (int) maxSize;
+        }
+
+        private int CompareAzureVersions(string a, string b)
+        {
+            var v1Parts = a.Split('-').Select(p => int.Parse(p));
+            var v2Parts = b.Split('-').Select(p => int.Parse(p));
+
+            return a[0] != b[0] ? a[0] - b[0] :
+                a[1] != b[1] ? a[1] - b[1] :
+                a[2] != b[2] ? a[2] - b[2] :
+                0;
+        }
+    }
+}
diff --git a/src/Core/Services/BitwardenFileUploadService.cs b/src/Core/Services/BitwardenFileUploadService.cs
new file mode 100644
index 000000000..372cd4a9f
--- /dev/null
+++ b/src/Core/Services/BitwardenFileUploadService.cs
@@ -0,0 +1,26 @@
+using System;
+using System.Net.Http;
+using System.Threading.Tasks;
+
+namespace Bit.Core.Services
+{
+    public class BitwardenFileUploadService
+    {
+        public BitwardenFileUploadService(ApiService apiService)
+        {
+            _apiService = apiService;
+        }
+
+        private readonly ApiService _apiService;
+
+        public async Task Upload(string encryptedFileName, byte[] encryptedFileData, Func<MultipartFormDataContent, Task> apiCall)
+        {
+            var fd = new MultipartFormDataContent($"--BWMobileFormBoundary{DateTime.UtcNow.Ticks}")
+            {
+                { new ByteArrayContent(encryptedFileData), "data", encryptedFileName }
+            };
+
+            await apiCall(fd);
+        }
+    }
+}
diff --git a/src/Core/Services/FileUploadService.cs b/src/Core/Services/FileUploadService.cs
new file mode 100644
index 000000000..03539f8aa
--- /dev/null
+++ b/src/Core/Services/FileUploadService.cs
@@ -0,0 +1,51 @@
+using System.Threading.Tasks;
+using Bit.Core.Abstractions;
+using Bit.Core.Models.Domain;
+using Bit.Core.Models.Response;
+using Bit.Core.Enums;
+using System;
+
+namespace Bit.Core.Services {
+    public class FileUploadService : IFileUploadService
+    {
+        public FileUploadService(ApiService apiService)
+        {
+            _apiService = apiService;
+            _bitwardenFileUploadService = new BitwardenFileUploadService(apiService);
+            _azureFileUploadService = new AzureFileUploadService();
+        }
+
+        private readonly BitwardenFileUploadService _bitwardenFileUploadService;
+        private readonly AzureFileUploadService _azureFileUploadService;
+        private readonly ApiService _apiService;
+
+        public async Task UploadSendFileAsync(SendFileUploadDataResponse uploadData, CipherString fileName, byte[] encryptedFileData)
+        {
+            try
+            {
+                switch (uploadData.FileUploadType)
+                {
+                    case FileUploadType.Direct:
+                        await _bitwardenFileUploadService.Upload(fileName.EncryptedString, encryptedFileData,
+                            fd => _apiService.PostSendFileAsync(uploadData.SendResponse.Id, uploadData.SendResponse.File.Id, fd));
+                        break;
+                    case FileUploadType.Azure:
+                        Func<Task<string>> renewalCallback = async () =>
+                        {
+                            var response = await _apiService.RenewFileUploadUrlAsync(uploadData.SendResponse.Id, uploadData.SendResponse.File.Id);
+                            return response.Url;
+                        };
+                        await _azureFileUploadService.Upload(uploadData.Url, encryptedFileData, renewalCallback);
+                        break;
+                    default:
+                        throw new Exception("Unknown file upload type");
+                }
+            }
+            catch (Exception e)
+            {
+                await _apiService.DeleteSendAsync(uploadData.SendResponse.Id);
+                throw e;
+            }
+        }
+    }
+}
diff --git a/src/Core/Services/SendService.cs b/src/Core/Services/SendService.cs
index af9c586f3..ee5a3b405 100644
--- a/src/Core/Services/SendService.cs
+++ b/src/Core/Services/SendService.cs
@@ -1,11 +1,12 @@
 using System;
 using System.Collections.Generic;
-using System.IO;
 using System.Linq;
+using System.Net;
 using System.Net.Http;
 using System.Threading.Tasks;
 using Bit.Core.Abstractions;
 using Bit.Core.Enums;
+using Bit.Core.Exceptions;
 using Bit.Core.Models.Data;
 using Bit.Core.Models.Domain;
 using Bit.Core.Models.Request;
@@ -25,11 +26,13 @@ namespace Bit.Core.Services
         private readonly II18nService _i18nService;
         private readonly ICryptoFunctionService _cryptoFunctionService;
         private Task<List<SendView>> _getAllDecryptedTask;
+        private readonly IFileUploadService _fileUploadService;
 
         public SendService(
             ICryptoService cryptoService,
             IUserService userService,
             IApiService apiService,
+            IFileUploadService fileUploadService,
             IStorageService storageService,
             II18nService i18nService,
             ICryptoFunctionService cryptoFunctionService)
@@ -37,6 +40,7 @@ namespace Bit.Core.Services
             _cryptoService = cryptoService;
             _userService = userService;
             _apiService = apiService;
+            _fileUploadService = fileUploadService;
             _storageService = storageService;
             _i18nService = i18nService;
             _cryptoFunctionService = cryptoFunctionService;
@@ -195,7 +199,7 @@ namespace Bit.Core.Services
         public async Task<string> SaveWithServerAsync(Send send, byte[] encryptedFileData)
         {
             var request = new SendRequest(send, encryptedFileData?.LongLength);
-            SendResponse response;
+            SendResponse response = default;
             if (send.Id == null)
             {
                 switch (send.Type)
@@ -204,13 +208,23 @@ namespace Bit.Core.Services
                         response = await _apiService.PostSendAsync(request);
                         break;
                     case SendType.File:
-                        var fd = new MultipartFormDataContent($"--BWMobileFormBoundary{DateTime.UtcNow.Ticks}")
-                        {
-                            { new StringContent(JsonConvert.SerializeObject(request)), "model" },
-                            { new ByteArrayContent(encryptedFileData), "data", send.File.FileName.EncryptedString }
-                        };
+                        try{
+                            var uploadDataResponse = await _apiService.PostFileTypeSendAsync(request);
+                            response = uploadDataResponse.SendResponse;
 
-                        response = await _apiService.PostSendFileAsync(fd);
+                            await _fileUploadService.UploadSendFileAsync(uploadDataResponse, send.File.FileName, encryptedFileData);
+                        }
+                        catch (ApiException e) when (e.Error.StatusCode == HttpStatusCode.NotFound)
+                        {
+                            response = await LegacyServerSendFileUpload(request, send, encryptedFileData);
+                        }
+                        catch (Exception e) 
+                        {
+                            if (response != default){
+                                await _apiService.DeleteSendAsync(response.Id);
+                            }
+                            throw e;
+                        }
                         break;
                     default:
                         throw new NotImplementedException($"Cannot save unknown Send type {send.Type}");
@@ -227,6 +241,17 @@ namespace Bit.Core.Services
             return response.Id;
         }
 
+        [Obsolete("Mar 25 2021: This method has been deprecated in favor of direct uploads. This method still exists for backward compatibility with old server versions.")]
+        private async Task<SendResponse> LegacyServerSendFileUpload(SendRequest request, Send send, byte[] encryptedFileData) {
+            var fd = new MultipartFormDataContent($"--BWMobileFormBoundary{DateTime.UtcNow.Ticks}")
+                        {
+                            { new StringContent(JsonConvert.SerializeObject(request)), "model" },
+                            { new ByteArrayContent(encryptedFileData), "data", send.File.FileName.EncryptedString }
+                        };
+
+            return await _apiService.PostSendFileAsync(fd);
+        }
+
         public async Task UpsertAsync(params SendData[] sends)
         {
             var userId = await _userService.GetUserIdAsync();
diff --git a/src/Core/Utilities/CoreHelpers.cs b/src/Core/Utilities/CoreHelpers.cs
index 0799906bb..e229a5969 100644
--- a/src/Core/Utilities/CoreHelpers.cs
+++ b/src/Core/Utilities/CoreHelpers.cs
@@ -80,7 +80,7 @@ namespace Bit.Core.Utilities
             return null;
         }
 
-        private static Uri GetUri(string uriString)
+        public static Uri GetUri(string uriString)
         {
             if (string.IsNullOrWhiteSpace(uriString))
             {
diff --git a/src/Core/Utilities/ServiceContainer.cs b/src/Core/Utilities/ServiceContainer.cs
index 0ae61b84a..ec5a9c578 100644
--- a/src/Core/Utilities/ServiceContainer.cs
+++ b/src/Core/Utilities/ServiceContainer.cs
@@ -40,13 +40,14 @@ namespace Bit.Core.Utilities
             var appIdService = new AppIdService(storageService);
             var userService = new UserService(storageService, tokenService);
             var settingsService = new SettingsService(userService, storageService);
+            var fileUploadService = new FileUploadService(apiService);
             var cipherService = new CipherService(cryptoService, userService, settingsService, apiService,
                 storageService, i18nService, () => searchService, clearCipherCacheKey, allClearCipherCacheKeys);
             var folderService = new FolderService(cryptoService, userService, apiService, storageService,
                 i18nService, cipherService);
             var collectionService = new CollectionService(cryptoService, userService, storageService, i18nService);
-            var sendService = new SendService(cryptoService, userService, apiService, storageService, i18nService,
-                cryptoFunctionService);
+            var sendService = new SendService(cryptoService, userService, apiService, fileUploadService, storageService,
+                i18nService, cryptoFunctionService);
             searchService = new SearchService(cipherService, sendService);
             var vaultTimeoutService = new VaultTimeoutService(cryptoService, userService, platformUtilsService, 
                 storageService, folderService, cipherService, collectionService, searchService, messagingService, tokenService,
diff --git a/test/Core.Test/Services/SendServiceTests.cs b/test/Core.Test/Services/SendServiceTests.cs
index 9df3d814f..fcdfc9ed7 100644
--- a/test/Core.Test/Services/SendServiceTests.cs
+++ b/test/Core.Test/Services/SendServiceTests.cs
@@ -21,6 +21,8 @@ using Bit.Core.Models.Request;
 using Bit.Core.Test.AutoFixture;
 using System.Linq.Expressions;
 using Bit.Core.Models.View;
+using Bit.Core.Exceptions;
+using NSubstitute.ExceptionExtensions;
 
 namespace Bit.Core.Test.Services
 {
@@ -172,7 +174,6 @@ namespace Bit.Core.Test.Services
             send.Id = null;
             sutProvider.GetDependency<IUserService>().GetUserIdAsync().Returns(userId);
             sutProvider.GetDependency<IApiService>().PostSendAsync(Arg.Any<SendRequest>()).Returns(response);
-            sutProvider.GetDependency<IApiService>().PostSendFileAsync(Arg.Any<MultipartFormDataContent>()).Returns(response);
 
             var fileContentBytes = Encoding.UTF8.GetBytes("This is the file content");
 
@@ -200,40 +201,43 @@ namespace Bit.Core.Test.Services
 
         [Theory]
         [InlineCustomAutoData(new[] { typeof(SutProviderCustomization), typeof(FileSendCustomization) })]
-        public async Task SaveWithServerAsync_NewFileSend_Success(SutProvider<SendService> sutProvider, string userId, SendResponse response, Send send)
+        public async Task SaveWithServerAsync_NewFileSend_AzureUpload_Success(SutProvider<SendService> sutProvider, string userId, SendFileUploadDataResponse response, Send send)
+        {
+            send.Id = null;
+            response.FileUploadType = FileUploadType.Azure;
+            sutProvider.GetDependency<IUserService>().GetUserIdAsync().Returns(userId);
+            sutProvider.GetDependency<IApiService>().PostFileTypeSendAsync(Arg.Any<SendRequest>()).Returns(response);
+
+            var fileContentBytes = Encoding.UTF8.GetBytes("This is the file content");
+
+            await sutProvider.Sut.SaveWithServerAsync(send, fileContentBytes);
+
+            switch (send.Type)
+            {
+                case SendType.File:
+                    await sutProvider.GetDependency<IFileUploadService>().Received(1).UploadSendFileAsync(response, send.File.FileName, fileContentBytes);
+                    break;
+                case SendType.Text:
+                default:
+                    throw new Exception("Untested send type");
+            }
+        }
+
+        [Theory]
+        [InlineCustomAutoData(new[] { typeof(SutProviderCustomization), typeof(FileSendCustomization) })]
+        public async Task SaveWithServerAsync_NewFileSend_LegacyFallback_Success(SutProvider<SendService> sutProvider, string userId, Send send, SendResponse response)
         {
             send.Id = null;
             sutProvider.GetDependency<IUserService>().GetUserIdAsync().Returns(userId);
-            sutProvider.GetDependency<IApiService>().PostSendAsync(Arg.Any<SendRequest>()).Returns(response);
+            var error = new ErrorResponse(null, System.Net.HttpStatusCode.NotFound);
+            sutProvider.GetDependency<IApiService>().PostFileTypeSendAsync(Arg.Any<SendRequest>()).Throws(new ApiException(error));
             sutProvider.GetDependency<IApiService>().PostSendFileAsync(Arg.Any<MultipartFormDataContent>()).Returns(response);
 
             var fileContentBytes = Encoding.UTF8.GetBytes("This is the file content");
 
             await sutProvider.Sut.SaveWithServerAsync(send, fileContentBytes);
 
-            Predicate<MultipartFormDataContent> formDataPredicate = fd =>
-            {
-                Assert.Equal(2, fd.Count()); // expect a request and file content
-
-                var expectedRequest = JsonConvert.SerializeObject(new SendRequest(send, fileContentBytes?.LongLength));
-                var actualRequest = fd.First().ReadAsStringAsync().GetAwaiter().GetResult();
-                Assert.Equal(expectedRequest, actualRequest);
-
-                var actualFileContent = fd.Skip(1).First().ReadAsByteArrayAsync().GetAwaiter().GetResult();
-                Assert.Equal(fileContentBytes, actualFileContent);
-                return true;
-            };
-
-            switch (send.Type)
-            {
-                case SendType.File:
-                    await sutProvider.GetDependency<IApiService>().Received(1)
-                        .PostSendFileAsync(Arg.Is<MultipartFormDataContent>(f => formDataPredicate(f)));
-                    break;
-                case SendType.Text:
-                default:
-                    throw new Exception("Untested send type");
-            }
+            await sutProvider.GetDependency<IApiService>().Received(1).PostSendFileAsync(Arg.Any<MultipartFormDataContent>());
         }
 
         [Theory]