diff --git a/build/dependencies.props b/build/dependencies.props
index f8d54b4212..53fad8ff02 100644
--- a/build/dependencies.props
+++ b/build/dependencies.props
@@ -21,6 +21,7 @@
     <MicrosoftNETCoreApp20PackageVersion>2.0.0</MicrosoftNETCoreApp20PackageVersion>
     <MicrosoftNETCoreApp21PackageVersion>2.1.0-preview2-26130-04</MicrosoftNETCoreApp21PackageVersion>
     <MicrosoftNETTestSdkPackageVersion>15.6.0</MicrosoftNETTestSdkPackageVersion>
+    <MoqPackageVersion>4.7.49</MoqPackageVersion>
     <XunitAnalyzersPackageVersion>0.8.0</XunitAnalyzersPackageVersion>
     <XunitPackageVersion>2.3.1</XunitPackageVersion>
     <XunitRunnerVisualStudioPackageVersion>2.4.0-beta.1.build3945</XunitRunnerVisualStudioPackageVersion>
diff --git a/src/Microsoft.AspNetCore.StaticFiles/StaticFileMiddleware.cs b/src/Microsoft.AspNetCore.StaticFiles/StaticFileMiddleware.cs
index d8910bcdbf..46594fc35d 100644
--- a/src/Microsoft.AspNetCore.StaticFiles/StaticFileMiddleware.cs
+++ b/src/Microsoft.AspNetCore.StaticFiles/StaticFileMiddleware.cs
@@ -3,6 +3,7 @@
 
 using System;
 using System.Diagnostics;
+using System.IO;
 using System.Threading.Tasks;
 using Microsoft.AspNetCore.Builder;
 using Microsoft.AspNetCore.Hosting;
@@ -67,7 +68,7 @@ namespace Microsoft.AspNetCore.StaticFiles
         /// </summary>
         /// <param name="context"></param>
         /// <returns></returns>
-        public Task Invoke(HttpContext context)
+        public async Task Invoke(HttpContext context)
         {
             var fileContext = new StaticFileContext(context, _options, _matchUrl, _logger, _fileProvider, _contentTypeProvider);
 
@@ -97,21 +98,36 @@ namespace Microsoft.AspNetCore.StaticFiles
                     case StaticFileContext.PreconditionState.ShouldProcess:
                         if (fileContext.IsHeadMethod)
                         {
-                            return fileContext.SendStatusAsync(Constants.Status200Ok);
+                            await fileContext.SendStatusAsync(Constants.Status200Ok);
+                            return;
                         }
-                        if (fileContext.IsRangeRequest)
+
+                        try
                         {
-                            return fileContext.SendRangeAsync();
+                            if (fileContext.IsRangeRequest)
+                            {
+                                await fileContext.SendRangeAsync();
+                                return;
+                            }
+
+                            await fileContext.SendAsync();
+                            _logger.LogFileServed(fileContext.SubPath, fileContext.PhysicalPath);
+                            return;
                         }
-                        _logger.LogFileServed(fileContext.SubPath, fileContext.PhysicalPath);
-                        return fileContext.SendAsync();
+                        catch (FileNotFoundException)
+                        {
+                            context.Response.Clear();
+                        }
+                        break;
                     case StaticFileContext.PreconditionState.NotModified:
                         _logger.LogPathNotModified(fileContext.SubPath);
-                        return fileContext.SendStatusAsync(Constants.Status304NotModified);
+                        await fileContext.SendStatusAsync(Constants.Status304NotModified);
+                        return;
 
                     case StaticFileContext.PreconditionState.PreconditionFailed:
                         _logger.LogPreconditionFailed(fileContext.SubPath);
-                        return fileContext.SendStatusAsync(Constants.Status412PreconditionFailed);
+                        await fileContext.SendStatusAsync(Constants.Status412PreconditionFailed);
+                        return;
 
                     default:
                         var exception = new NotImplementedException(fileContext.GetPreconditionState().ToString());
@@ -120,7 +136,7 @@ namespace Microsoft.AspNetCore.StaticFiles
                 }
             }
 
-            return _next(context);
+            await _next(context);
         }
     }
 }
diff --git a/test/Microsoft.AspNetCore.StaticFiles.Tests/Microsoft.AspNetCore.StaticFiles.Tests.csproj b/test/Microsoft.AspNetCore.StaticFiles.Tests/Microsoft.AspNetCore.StaticFiles.Tests.csproj
index 9a59dfca29..5826c54b9c 100644
--- a/test/Microsoft.AspNetCore.StaticFiles.Tests/Microsoft.AspNetCore.StaticFiles.Tests.csproj
+++ b/test/Microsoft.AspNetCore.StaticFiles.Tests/Microsoft.AspNetCore.StaticFiles.Tests.csproj
@@ -18,6 +18,7 @@
 
   <ItemGroup>
     <PackageReference Include="Microsoft.AspNetCore.TestHost" Version="$(MicrosoftAspNetCoreTestHostPackageVersion)" />
+    <PackageReference Include="Moq" Version="$(MoqPackageVersion)" />
   </ItemGroup>
 
 </Project>
diff --git a/test/Microsoft.AspNetCore.StaticFiles.Tests/StaticFileMiddlewareTests.cs b/test/Microsoft.AspNetCore.StaticFiles.Tests/StaticFileMiddlewareTests.cs
index 7517782e51..31c6894d2b 100644
--- a/test/Microsoft.AspNetCore.StaticFiles.Tests/StaticFileMiddlewareTests.cs
+++ b/test/Microsoft.AspNetCore.StaticFiles.Tests/StaticFileMiddlewareTests.cs
@@ -3,16 +3,20 @@
 
 using System;
 using System.Collections.Generic;
+using System.Diagnostics;
 using System.IO;
 using System.Linq;
 using System.Net;
+using System.Threading;
 using System.Threading.Tasks;
 using Microsoft.AspNetCore.Builder;
 using Microsoft.AspNetCore.Hosting;
 using Microsoft.AspNetCore.Http;
+using Microsoft.AspNetCore.Http.Features;
 using Microsoft.AspNetCore.TestHost;
 using Microsoft.AspNetCore.Testing.xunit;
 using Microsoft.Extensions.FileProviders;
+using Moq;
 using Xunit;
 
 namespace Microsoft.AspNetCore.StaticFiles
@@ -29,6 +33,59 @@ namespace Microsoft.AspNetCore.StaticFiles
             var response = await server.CreateClient().GetAsync("/ranges.txt");
 
             Assert.Equal(HttpStatusCode.NotFound, response.StatusCode);
+            Assert.Null(response.Headers.ETag);
+        }
+
+        [ConditionalFact]
+        [OSSkipCondition(OperatingSystems.Windows, SkipReason = "Symlinks not supported on Windows")]
+        public async Task ReturnsNotFoundForBrokenSymlink()
+        {
+            var badLink = Path.Combine(AppContext.BaseDirectory, Path.GetRandomFileName() + ".txt");
+
+            Process.Start("ln", $"-s \"/tmp/{Path.GetRandomFileName()}\" \"{badLink}\"").WaitForExit();
+            Assert.True(File.Exists(badLink), "Should have created a symlink");
+
+            try
+            {
+                var builder = new WebHostBuilder()
+                    .Configure(app => app.UseStaticFiles(new StaticFileOptions { ServeUnknownFileTypes = true }))
+                    .UseWebRoot(AppContext.BaseDirectory);
+                var server = new TestServer(builder);
+
+                var response = await server.CreateClient().GetAsync(Path.GetFileName(badLink));
+
+                Assert.Equal(HttpStatusCode.NotFound, response.StatusCode);
+                Assert.Null(response.Headers.ETag);
+            }
+            finally
+            {
+                File.Delete(badLink);
+            }
+        }
+
+        [Fact]
+        public async Task ReturnsNotFoundIfSendFileThrows()
+        {
+            var mockSendFile = new Mock<IHttpSendFileFeature>();
+            mockSendFile.Setup(m => m.SendFileAsync(It.IsAny<string>(), It.IsAny<long>(), It.IsAny<long?>(), It.IsAny<CancellationToken>()))
+                .ThrowsAsync(new FileNotFoundException());
+            var builder = new WebHostBuilder()
+                .Configure(app =>
+                {
+                    app.Use(async (ctx, next) =>
+                    {
+                        ctx.Features.Set(mockSendFile.Object);
+                        await next();
+                    });
+                    app.UseStaticFiles(new StaticFileOptions { ServeUnknownFileTypes = true });
+                })
+                .UseWebRoot(AppContext.BaseDirectory);
+            var server = new TestServer(builder);
+
+            var response = await server.CreateClient().GetAsync("TestDocument.txt");
+
+            Assert.Equal(HttpStatusCode.NotFound, response.StatusCode);
+            Assert.Null(response.Headers.ETag);
         }
 
         [Fact]
@@ -101,6 +158,7 @@ namespace Microsoft.AspNetCore.StaticFiles
                 Assert.Equal("text/plain", response.Content.Headers.ContentType.ToString());
                 Assert.True(response.Content.Headers.ContentLength == fileInfo.Length);
                 Assert.Equal(response.Content.Headers.ContentLength, responseContent.Length);
+                Assert.NotNull(response.Headers.ETag);
 
                 using (var stream = fileInfo.CreateReadStream())
                 {