diff --git a/Octokit.Tests.Integration/Clients/RepositoryContentsClientTests.cs b/Octokit.Tests.Integration/Clients/RepositoryContentsClientTests.cs
index 2cc8cf7013..e1d70edfa0 100644
--- a/Octokit.Tests.Integration/Clients/RepositoryContentsClientTests.cs
+++ b/Octokit.Tests.Integration/Clients/RepositoryContentsClientTests.cs
@@ -469,6 +469,182 @@ await Assert.ThrowsAsync<NotFoundException>(
             }
         }
 
+        [IntegrationTest]
+        public async Task CrudTestWithExplicitBase64()
+        {
+            var client = Helper.GetAuthenticatedClient();
+            var fixture = client.Repository.Content;
+            var repoName = Helper.MakeNameWithTimestamp("source-repo");
+
+            using (var context = await client.CreateRepositoryContext(new NewRepository(repoName) { AutoInit = true }))
+            {
+                var repository = context.Repository;
+
+                var file = await fixture.CreateFile(
+                    repository.Owner.Login,
+                    repository.Name,
+                    "somefile.txt",
+                    new CreateFileRequest("Test commit", "U29tZSBDb250ZW50", false));
+                Assert.Equal("somefile.txt", file.Content.Name);
+
+                var contents = await fixture.GetAllContents(repository.Owner.Login, repository.Name, "somefile.txt");
+                string fileSha = contents.First().Sha;
+                Assert.Equal("Some Content", contents.First().Content);
+
+                var update = await fixture.UpdateFile(
+                    repository.Owner.Login,
+                    repository.Name,
+                    "somefile.txt",
+                    new UpdateFileRequest("Updating file", "TmV3IENvbnRlbnQ=", fileSha, false));
+                Assert.Equal("somefile.txt", update.Content.Name);
+
+                contents = await fixture.GetAllContents(repository.Owner.Login, repository.Name, "somefile.txt");
+                Assert.Equal("New Content", contents.First().Content);
+                fileSha = contents.First().Sha;
+
+                await fixture.DeleteFile(
+                    repository.Owner.Login,
+                    repository.Name,
+                    "somefile.txt",
+                    new DeleteFileRequest("Deleted file", fileSha));
+
+                await Assert.ThrowsAsync<NotFoundException>(
+                     () => fixture.GetAllContents(repository.Owner.Login, repository.Name, "somefile.txt"));
+            }
+        }
+
+        [IntegrationTest]
+        public async Task CrudTestWithRepositoryIdWithExplicitBase64()
+        {
+            var client = Helper.GetAuthenticatedClient();
+            var fixture = client.Repository.Content;
+            var repoName = Helper.MakeNameWithTimestamp("source-repo");
+
+            using (var context = await client.CreateRepositoryContext(new NewRepository(repoName) { AutoInit = true }))
+            {
+                var repository = context.Repository;
+
+                var file = await fixture.CreateFile(
+                    repository.Id,
+                    "somefile.txt",
+                    new CreateFileRequest("Test commit", "U29tZSBDb250ZW50", false));
+                Assert.Equal("somefile.txt", file.Content.Name);
+
+                var contents = await fixture.GetAllContents(repository.Owner.Login, repository.Name, "somefile.txt");
+                string fileSha = contents.First().Sha;
+                Assert.Equal("Some Content", contents.First().Content);
+
+                var update = await fixture.UpdateFile(
+                    repository.Id,
+                    "somefile.txt",
+                    new UpdateFileRequest("Updating file", "TmV3IENvbnRlbnQ=", fileSha, false));
+                Assert.Equal("somefile.txt", update.Content.Name);
+
+                contents = await fixture.GetAllContents(repository.Owner.Login, repository.Name, "somefile.txt");
+                Assert.Equal("New Content", contents.First().Content);
+                fileSha = contents.First().Sha;
+
+                await fixture.DeleteFile(
+                    repository.Id,
+                    "somefile.txt",
+                    new DeleteFileRequest("Deleted file", fileSha));
+
+                await Assert.ThrowsAsync<NotFoundException>(
+                     () => fixture.GetAllContents(repository.Owner.Login, repository.Name, "somefile.txt"));
+            }
+        }
+
+        [IntegrationTest]
+        public async Task CrudTestWithNamedBranchWithExplicitBase64()
+        {
+            var client = Helper.GetAuthenticatedClient();
+            var fixture = client.Repository.Content;
+            var repoName = Helper.MakeNameWithTimestamp("source-repo");
+            var branchName = "other-branch";
+
+            using (var context = await client.CreateRepositoryContext(new NewRepository(repoName) { AutoInit = true }))
+            {
+                var repository = context.Repository;
+
+                var master = await client.Git.Reference.Get(Helper.UserName, repository.Name, "heads/master");
+                await client.Git.Reference.Create(Helper.UserName, repository.Name, new NewReference("refs/heads/" + branchName, master.Object.Sha));
+                var file = await fixture.CreateFile(
+                    repository.Owner.Login,
+                    repository.Name,
+                    "somefile.txt",
+                    new CreateFileRequest("Test commit", "U29tZSBDb250ZW50", branchName, false));
+                Assert.Equal("somefile.txt", file.Content.Name);
+
+                var contents = await fixture.GetAllContentsByRef(repository.Owner.Login, repository.Name, "somefile.txt", branchName);
+                string fileSha = contents.First().Sha;
+                Assert.Equal("Some Content", contents.First().Content);
+
+                var update = await fixture.UpdateFile(
+                    repository.Owner.Login,
+                    repository.Name,
+                    "somefile.txt",
+                    new UpdateFileRequest("Updating file", "TmV3IENvbnRlbnQ=", fileSha, branchName, false));
+                Assert.Equal("somefile.txt", update.Content.Name);
+
+                contents = await fixture.GetAllContentsByRef(repository.Owner.Login, repository.Name, "somefile.txt", branchName);
+                Assert.Equal("New Content", contents.First().Content);
+                fileSha = contents.First().Sha;
+
+                await fixture.DeleteFile(
+                    repository.Owner.Login,
+                    repository.Name,
+                    "somefile.txt",
+                    new DeleteFileRequest("Deleted file", fileSha, branchName));
+
+                await Assert.ThrowsAsync<NotFoundException>(
+                    () => fixture.GetAllContents(repository.Owner.Login, repository.Name, "somefile.txt"));
+            }
+        }
+
+        [IntegrationTest]
+        public async Task CrudTestWithNamedBranchWithRepositoryIdWithExplicitBase64()
+        {
+            var client = Helper.GetAuthenticatedClient();
+            var fixture = client.Repository.Content;
+            var repoName = Helper.MakeNameWithTimestamp("source-repo");
+            var branchName = "other-branch";
+
+            using (var context = await client.CreateRepositoryContext(new NewRepository(repoName) { AutoInit = true }))
+            {
+                var repository = context.Repository;
+
+                var master = await client.Git.Reference.Get(Helper.UserName, repository.Name, "heads/master");
+                await client.Git.Reference.Create(Helper.UserName, repository.Name, new NewReference("refs/heads/" + branchName, master.Object.Sha));
+                var file = await fixture.CreateFile(
+                    repository.Id,
+                    "somefile.txt",
+                    new CreateFileRequest("Test commit", "U29tZSBDb250ZW50", branchName, false));
+                Assert.Equal("somefile.txt", file.Content.Name);
+
+                var contents = await fixture.GetAllContentsByRef(repository.Owner.Login, repository.Name, "somefile.txt", branchName);
+                string fileSha = contents.First().Sha;
+                Assert.Equal("Some Content", contents.First().Content);
+
+                var update = await fixture.UpdateFile(
+                    repository.Id,
+                    "somefile.txt",
+                    new UpdateFileRequest("Updating file", "TmV3IENvbnRlbnQ=", fileSha, branchName, false));
+                Assert.Equal("somefile.txt", update.Content.Name);
+
+                contents = await fixture.GetAllContentsByRef(repository.Owner.Login, repository.Name, "somefile.txt", branchName);
+                Assert.Equal("New Content", contents.First().Content);
+                fileSha = contents.First().Sha;
+
+                await fixture.DeleteFile(
+                    repository.Id,
+                    "somefile.txt",
+                    new DeleteFileRequest("Deleted file", fileSha, branchName));
+
+                await Assert.ThrowsAsync<NotFoundException>(
+                    () => fixture.GetAllContents(repository.Owner.Login, repository.Name, "somefile.txt"));
+            }
+        }
+
         public class TheGetArchiveMethod
         {
             [IntegrationTest(Skip = "this will probably take too long")]
diff --git a/Octokit.Tests/Clients/RepositoryContentsClientTests.cs b/Octokit.Tests/Clients/RepositoryContentsClientTests.cs
index f04ca7da42..58a04b4ec9 100644
--- a/Octokit.Tests/Clients/RepositoryContentsClientTests.cs
+++ b/Octokit.Tests/Clients/RepositoryContentsClientTests.cs
@@ -349,7 +349,7 @@ public async Task PassesRequestObject()
                     Arg.Any<Uri>(),
                     Arg.Is<CreateFileRequest>(a =>
                         a.Message == "message"
-                        && a.Content == "myfilecontents"
+                        && a.Content == "bXlmaWxlY29udGVudHM="
                         && a.Branch == "mybranch"));
             }
 
@@ -365,7 +365,63 @@ public async Task PassesRequestObjectWithRepositoryId()
                     Arg.Any<Uri>(),
                     Arg.Is<CreateFileRequest>(a =>
                         a.Message == "message"
-                        && a.Content == "myfilecontents"
+                        && a.Content == "bXlmaWxlY29udGVudHM="
+                        && a.Branch == "mybranch"));
+            }
+
+            [Fact]
+            public async Task RequestsCorrectUrlWithExplicitBase64()
+            {
+                var connection = Substitute.For<IApiConnection>();
+                var client = new RepositoryContentsClient(connection);
+
+                string expectedUri = "repos/org/repo/contents/path/to/file";
+                await client.CreateFile("org", "repo", "path/to/file", new CreateFileRequest("message", "bXlmaWxlY29udGVudHM=", "mybranch", false));
+
+                connection.Received().Put<RepositoryContentChangeSet>(Arg.Is<Uri>(u => u.ToString() == expectedUri), Arg.Any<object>());
+            }
+
+            [Fact]
+            public async Task RequestsCorrectUrlWithRepositoryIdWithExplicitBase64()
+            {
+                var connection = Substitute.For<IApiConnection>();
+                var client = new RepositoryContentsClient(connection);
+
+                string expectedUri = "repositories/1/contents/path/to/file";
+                await client.CreateFile(1, "path/to/file", new CreateFileRequest("message", "bXlmaWxlY29udGVudHM=", "mybranch", false));
+
+                connection.Received().Put<RepositoryContentChangeSet>(Arg.Is<Uri>(u => u.ToString() == expectedUri), Arg.Any<object>());
+            }
+
+            [Fact]
+            public async Task PassesRequestObjectWithExplicitBase64()
+            {
+                var connection = Substitute.For<IApiConnection>();
+                var client = new RepositoryContentsClient(connection);
+
+                await client.CreateFile("org", "repo", "path/to/file", new CreateFileRequest("message", "bXlmaWxlY29udGVudHM=", "mybranch", false));
+
+                connection.Received().Put<RepositoryContentChangeSet>(
+                    Arg.Any<Uri>(),
+                    Arg.Is<CreateFileRequest>(a =>
+                        a.Message == "message"
+                        && a.Content == "bXlmaWxlY29udGVudHM="
+                        && a.Branch == "mybranch"));
+            }
+
+            [Fact]
+            public async Task PassesRequestObjectWithRepositoryIdWithExplicitBase64()
+            {
+                var connection = Substitute.For<IApiConnection>();
+                var client = new RepositoryContentsClient(connection);
+
+                await client.CreateFile(1, "path/to/file", new CreateFileRequest("message", "bXlmaWxlY29udGVudHM=", "mybranch", false));
+
+                connection.Received().Put<RepositoryContentChangeSet>(
+                    Arg.Any<Uri>(),
+                    Arg.Is<CreateFileRequest>(a =>
+                        a.Message == "message"
+                        && a.Content == "bXlmaWxlY29udGVudHM="
                         && a.Branch == "mybranch"));
             }
 
@@ -509,7 +565,7 @@ public async Task PassesRequestObject()
                     Arg.Any<Uri>(),
                     Arg.Is<UpdateFileRequest>(a =>
                         a.Message == "message"
-                        && a.Content == "myfilecontents"
+                        && a.Content == "bXlmaWxlY29udGVudHM="
                         && a.Sha == "1234abc"
                         && a.Branch == "mybranch"));
             }
@@ -526,7 +582,65 @@ public async Task PassesRequestObjectWithRepositoriesId()
                     Arg.Any<Uri>(),
                     Arg.Is<UpdateFileRequest>(a =>
                         a.Message == "message"
-                        && a.Content == "myfilecontents"
+                        && a.Content == "bXlmaWxlY29udGVudHM="
+                        && a.Sha == "1234abc"
+                        && a.Branch == "mybranch"));
+            }
+
+            [Fact]
+            public async Task RequestsCorrectUrlWithExplicitBase64()
+            {
+                var connection = Substitute.For<IApiConnection>();
+                var client = new RepositoryContentsClient(connection);
+
+                string expectedUri = "repos/org/repo/contents/path/to/file";
+                await client.UpdateFile("org", "repo", "path/to/file", new UpdateFileRequest("message", "bXlmaWxlY29udGVudHM=", "1234abc", "mybranch", false));
+
+                connection.Received().Put<RepositoryContentChangeSet>(Arg.Is<Uri>(u => u.ToString() == expectedUri), Arg.Any<object>());
+            }
+
+            [Fact]
+            public async Task RequestsCorrectUrlWithRepositoryIdWithExplicitBase64()
+            {
+                var connection = Substitute.For<IApiConnection>();
+                var client = new RepositoryContentsClient(connection);
+
+                string expectedUri = "repositories/1/contents/path/to/file";
+                await client.UpdateFile(1, "path/to/file", new UpdateFileRequest("message", "bXlmaWxlY29udGVudHM=", "1234abc", "mybranch", false));
+
+                connection.Received().Put<RepositoryContentChangeSet>(Arg.Is<Uri>(u => u.ToString() == expectedUri), Arg.Any<object>());
+            }
+
+            [Fact]
+            public async Task PassesRequestObjectWithExplicitBase64()
+            {
+                var connection = Substitute.For<IApiConnection>();
+                var client = new RepositoryContentsClient(connection);
+
+                await client.UpdateFile("org", "repo", "path/to/file", new UpdateFileRequest("message", "bXlmaWxlY29udGVudHM=", "1234abc", "mybranch", false));
+
+                connection.Received().Put<RepositoryContentChangeSet>(
+                    Arg.Any<Uri>(),
+                    Arg.Is<UpdateFileRequest>(a =>
+                        a.Message == "message"
+                        && a.Content == "bXlmaWxlY29udGVudHM="
+                        && a.Sha == "1234abc"
+                        && a.Branch == "mybranch"));
+            }
+
+            [Fact]
+            public async Task PassesRequestObjectWithRepositoriesIdWithExplicitBase64()
+            {
+                var connection = Substitute.For<IApiConnection>();
+                var client = new RepositoryContentsClient(connection);
+
+                await client.UpdateFile(1, "path/to/file", new UpdateFileRequest("message", "bXlmaWxlY29udGVudHM=", "1234abc", "mybranch", false));
+
+                connection.Received().Put<RepositoryContentChangeSet>(
+                    Arg.Any<Uri>(),
+                    Arg.Is<UpdateFileRequest>(a =>
+                        a.Message == "message"
+                        && a.Content == "bXlmaWxlY29udGVudHM="
                         && a.Sha == "1234abc"
                         && a.Branch == "mybranch"));
             }
diff --git a/Octokit.Tests/Reactive/ObservableRepositoryContentsClientTests.cs b/Octokit.Tests/Reactive/ObservableRepositoryContentsClientTests.cs
index f374f9b07f..7bdc3154a6 100644
--- a/Octokit.Tests/Reactive/ObservableRepositoryContentsClientTests.cs
+++ b/Octokit.Tests/Reactive/ObservableRepositoryContentsClientTests.cs
@@ -437,7 +437,7 @@ public void PassesRequestObject()
                     Arg.Any<Uri>(),
                     Arg.Is<CreateFileRequest>(a =>
                         a.Message == "message"
-                        && a.Content == "myfilecontents"
+                        && a.Content == "bXlmaWxlY29udGVudHM="
                         && a.Branch == "mybranch"));
             }
 
@@ -454,7 +454,66 @@ public void PassesRequestObjectWithRepositoryId()
                     Arg.Any<Uri>(),
                     Arg.Is<CreateFileRequest>(a =>
                         a.Message == "message"
-                        && a.Content == "myfilecontents"
+                        && a.Content == "bXlmaWxlY29udGVudHM="
+                        && a.Branch == "mybranch"));
+            }
+            [Fact]
+            public void RequestsCorrectUrlWithExplicitBase64()
+            {
+                var connection = Substitute.For<IConnection>();
+                var gitHubClient = new GitHubClient(connection);
+                var client = new ObservableRepositoryContentsClient(gitHubClient);
+
+                string expectedUri = "repos/org/repo/contents/path/to/file";
+                client.CreateFile("org", "repo", "path/to/file", new CreateFileRequest("message", "bXlmaWxlY29udGVudHM=", "mybranch", false));
+
+                gitHubClient.Connection.Received().Put<RepositoryContentChangeSet>(Arg.Is<Uri>(u => u.ToString() == expectedUri), Arg.Any<object>());
+            }
+
+            [Fact]
+            public void RequestsCorrectUrlWithRepositoryIdWithExplicitBase64()
+            {
+                var connection = Substitute.For<IConnection>();
+                var gitHubClient = new GitHubClient(connection);
+                var client = new ObservableRepositoryContentsClient(gitHubClient);
+
+                string expectedUri = "repositories/1/contents/path/to/file";
+                client.CreateFile(1, "path/to/file", new CreateFileRequest("message", "bXlmaWxlY29udGVudHM=", "mybranch", false));
+
+                gitHubClient.Connection.Received().Put<RepositoryContentChangeSet>(Arg.Is<Uri>(u => u.ToString() == expectedUri), Arg.Any<object>());
+            }
+
+            [Fact]
+            public void PassesRequestObjectWithExplicitBase64()
+            {
+                var connection = Substitute.For<IConnection>();
+                var gitHubClient = new GitHubClient(connection);
+                var client = new ObservableRepositoryContentsClient(gitHubClient);
+
+                client.CreateFile("org", "repo", "path/to/file", new CreateFileRequest("message", "bXlmaWxlY29udGVudHM=", "mybranch", false));
+
+                gitHubClient.Connection.Received().Put<RepositoryContentChangeSet>(
+                    Arg.Any<Uri>(),
+                    Arg.Is<CreateFileRequest>(a =>
+                        a.Message == "message"
+                        && a.Content == "bXlmaWxlY29udGVudHM="
+                        && a.Branch == "mybranch"));
+            }
+
+            [Fact]
+            public void PassesRequestObjectWithRepositoryIdWithExplicitBase64()
+            {
+                var connection = Substitute.For<IConnection>();
+                var gitHubClient = new GitHubClient(connection);
+                var client = new ObservableRepositoryContentsClient(gitHubClient);
+
+                client.CreateFile(1, "path/to/file", new CreateFileRequest("message", "bXlmaWxlY29udGVudHM=", "mybranch", false));
+
+                gitHubClient.Connection.Received().Put<RepositoryContentChangeSet>(
+                    Arg.Any<Uri>(),
+                    Arg.Is<CreateFileRequest>(a =>
+                        a.Message == "message"
+                        && a.Content == "bXlmaWxlY29udGVudHM="
                         && a.Branch == "mybranch"));
             }
 
@@ -606,7 +665,7 @@ public void PassesRequestObject()
                     Arg.Any<Uri>(),
                     Arg.Is<UpdateFileRequest>(a =>
                         a.Message == "message"
-                        && a.Content == "myfilecontents"
+                        && a.Content == "bXlmaWxlY29udGVudHM="
                         && a.Sha == "1234abc"
                         && a.Branch == "mybranch"));
             }
@@ -624,7 +683,69 @@ public void PassesRequestObjectWithRepositoriesId()
                     Arg.Any<Uri>(),
                     Arg.Is<UpdateFileRequest>(a =>
                         a.Message == "message"
-                        && a.Content == "myfilecontents"
+                        && a.Content == "bXlmaWxlY29udGVudHM="
+                        && a.Sha == "1234abc"
+                        && a.Branch == "mybranch"));
+            }
+
+            [Fact]
+            public void RequestsCorrectUrlWithExplicitBase64()
+            {
+                var connection = Substitute.For<IConnection>();
+                var gitHubClient = new GitHubClient(connection);
+                var client = new ObservableRepositoryContentsClient(gitHubClient);
+
+                string expectedUri = "repos/org/repo/contents/path/to/file";
+                client.UpdateFile("org", "repo", "path/to/file", new UpdateFileRequest("message", "bXlmaWxlY29udGVudHM=", "1234abc", "mybranch", false));
+
+                gitHubClient.Connection.Received().Put<RepositoryContentChangeSet>(Arg.Is<Uri>(u => u.ToString() == expectedUri), Arg.Any<object>());
+            }
+
+            [Fact]
+            public void RequestsCorrectUrlWithRepositoryIdWithExplicitBase64()
+            {
+                var connection = Substitute.For<IConnection>();
+                var gitHubClient = new GitHubClient(connection);
+                var client = new ObservableRepositoryContentsClient(gitHubClient);
+
+                string expectedUri = "repositories/1/contents/path/to/file";
+                client.UpdateFile(1, "path/to/file", new UpdateFileRequest("message", "bXlmaWxlY29udGVudHM=", "1234abc", "mybranch", false));
+
+                gitHubClient.Connection.Received().Put<RepositoryContentChangeSet>(Arg.Is<Uri>(u => u.ToString() == expectedUri), Arg.Any<object>());
+            }
+
+            [Fact]
+            public void PassesRequestObjectWithExplicitBase64()
+            {
+                var connection = Substitute.For<IConnection>();
+                var gitHubClient = new GitHubClient(connection);
+                var client = new ObservableRepositoryContentsClient(gitHubClient);
+
+                client.UpdateFile("org", "repo", "path/to/file", new UpdateFileRequest("message", "bXlmaWxlY29udGVudHM=", "1234abc", "mybranch", false));
+
+                gitHubClient.Connection.Received().Put<RepositoryContentChangeSet>(
+                    Arg.Any<Uri>(),
+                    Arg.Is<UpdateFileRequest>(a =>
+                        a.Message == "message"
+                        && a.Content == "bXlmaWxlY29udGVudHM="
+                        && a.Sha == "1234abc"
+                        && a.Branch == "mybranch"));
+            }
+
+            [Fact]
+            public void PassesRequestObjectWithRepositoriesIdWithExplicitBase64()
+            {
+                var connection = Substitute.For<IConnection>();
+                var gitHubClient = new GitHubClient(connection);
+                var client = new ObservableRepositoryContentsClient(gitHubClient);
+
+                client.UpdateFile(1, "path/to/file", new UpdateFileRequest("message", "bXlmaWxlY29udGVudHM=", "1234abc", "mybranch", false));
+
+                gitHubClient.Connection.Received().Put<RepositoryContentChangeSet>(
+                    Arg.Any<Uri>(),
+                    Arg.Is<UpdateFileRequest>(a =>
+                        a.Message == "message"
+                        && a.Content == "bXlmaWxlY29udGVudHM="
                         && a.Sha == "1234abc"
                         && a.Branch == "mybranch"));
             }
diff --git a/Octokit/Models/Request/CreateFileRequest.cs b/Octokit/Models/Request/CreateFileRequest.cs
index b54dfee3d2..06d6f5e133 100644
--- a/Octokit/Models/Request/CreateFileRequest.cs
+++ b/Octokit/Models/Request/CreateFileRequest.cs
@@ -107,10 +107,32 @@ public class CreateFileRequest : ContentRequest
         /// </summary>
         /// <param name="message">The message.</param>
         /// <param name="content">The content.</param>
-        public CreateFileRequest(string message, string content) : base(message)
+        public CreateFileRequest(string message, string content) : this(message, content, true)
+        { }
+
+        /// <summary>
+        /// Initializes a new instance of the <see cref="CreateFileRequest"/> class.
+        /// </summary>
+        /// <param name="message">The message.</param>
+        /// <param name="content">The content.</param>
+        /// <param name="branch">The branch the request is for.</param>
+        public CreateFileRequest(string message, string content, string branch) : this(message, content, branch, true)
+        { }
+
+        /// <summary>
+        /// Creates an instance of a <see cref="CreateFileRequest" />.
+        /// </summary>
+        /// <param name="message">The message.</param>
+        /// <param name="content">The content.</param>
+        /// <param name="convertContentToBase64">True to convert content to base64.</param>
+        public CreateFileRequest(string message, string content, bool convertContentToBase64) : base(message)
         {
             Ensure.ArgumentNotNull(content, "content");
 
+            if (convertContentToBase64)
+            {
+                content = content.ToBase64String();
+            }
             Content = content;
         }
 
@@ -120,16 +142,21 @@ public CreateFileRequest(string message, string content) : base(message)
         /// <param name="message">The message.</param>
         /// <param name="content">The content.</param>
         /// <param name="branch">The branch the request is for.</param>
-        public CreateFileRequest(string message, string content, string branch) : base(message, branch)
+        /// <param name="convertContentToBase64">True to convert content to base64.</param>
+        public CreateFileRequest(string message, string content, string branch, bool convertContentToBase64) : base(message, branch)
         {
             Ensure.ArgumentNotNullOrEmptyString(content, "content");
 
+            if (convertContentToBase64)
+            {
+                content = content.ToBase64String();
+            }
             Content = content;
         }
+
         /// <summary>
-        /// The contents of the file to create. This is required.
+        /// The contents of the file to create, Base64 encoded. This is required.
         /// </summary>
-        [SerializeAsBase64]
         public string Content { get; private set; }
 
         internal virtual string DebuggerDisplay
@@ -154,7 +181,29 @@ public class UpdateFileRequest : CreateFileRequest
         /// <param name="content">The content.</param>
         /// <param name="sha">The sha.</param>
         public UpdateFileRequest(string message, string content, string sha)
-            : base(message, content)
+            : this(message, content, sha, true)
+        { }
+
+        /// <summary>
+        /// Creates an instance of a <see cref="UpdateFileRequest" />.
+        /// </summary>
+        /// <param name="message">The message.</param>
+        /// <param name="content">The content.</param>
+        /// <param name="sha">The sha.</param>
+        /// <param name="branch">The branch the request is for.</param>
+        public UpdateFileRequest(string message, string content, string sha, string branch)
+           : this(message, content, sha, branch, true)
+        { }
+
+        /// <summary>
+        /// Creates an instance of a <see cref="UpdateFileRequest" />.
+        /// </summary>
+        /// <param name="message">The message.</param>
+        /// <param name="content">The content.</param>
+        /// <param name="sha">The sha.</param>
+        /// <param name="convertContentToBase64">True to convert content to base64.</param>
+        public UpdateFileRequest(string message, string content, string sha, bool convertContentToBase64)
+            : base(message, content, convertContentToBase64)
         {
             Ensure.ArgumentNotNullOrEmptyString(sha, "sha");
 
@@ -168,8 +217,9 @@ public UpdateFileRequest(string message, string content, string sha)
         /// <param name="content">The content.</param>
         /// <param name="sha">The sha.</param>
         /// <param name="branch">The branch the request is for.</param>
-        public UpdateFileRequest(string message, string content, string sha, string branch)
-           : base(message, content, branch)
+        /// <param name="convertContentToBase64">True to convert content to base64.</param>
+        public UpdateFileRequest(string message, string content, string sha, string branch, bool convertContentToBase64)
+           : base(message, content, branch, convertContentToBase64)
         {
             Ensure.ArgumentNotNullOrEmptyString(sha, "sha");