diff --git a/src/Microsoft.AspNetCore.Server.Kestrel/Internal/Http/Frame.cs b/src/Microsoft.AspNetCore.Server.Kestrel/Internal/Http/Frame.cs
index 725e284bc6..307ce7bc49 100644
--- a/src/Microsoft.AspNetCore.Server.Kestrel/Internal/Http/Frame.cs
+++ b/src/Microsoft.AspNetCore.Server.Kestrel/Internal/Http/Frame.cs
@@ -520,6 +520,9 @@ namespace Microsoft.AspNetCore.Server.Kestrel.Internal.Http
 
         public void Write(ArraySegment<byte> data)
         {
+            // For the first write, ensure headers are flushed if Write(Chunked)isn't called.
+            var firstWrite = !HasResponseStarted;
+
             VerifyAndUpdateWrite(data.Count);
             ProduceStartAndFireOnStarting().GetAwaiter().GetResult();
 
@@ -529,6 +532,10 @@ namespace Microsoft.AspNetCore.Server.Kestrel.Internal.Http
                 {
                     if (data.Count == 0)
                     {
+                        if (firstWrite)
+                        {
+                            Flush();
+                        }
                         return;
                     }
                     WriteChunked(data);
@@ -541,6 +548,11 @@ namespace Microsoft.AspNetCore.Server.Kestrel.Internal.Http
             else
             {
                 HandleNonBodyResponseWrite();
+
+                if (firstWrite)
+                {
+                    Flush();
+                }
             }
         }
 
@@ -581,14 +593,18 @@ namespace Microsoft.AspNetCore.Server.Kestrel.Internal.Http
 
             await ProduceStartAndFireOnStarting();
 
+            // WriteAsyncAwaited is only called for the first write to the body.
+            // Ensure headers are flushed if Write(Chunked)Async isn't called.
             if (_canHaveBody)
             {
                 if (_autoChunk)
                 {
                     if (data.Count == 0)
                     {
+                        await FlushAsync(cancellationToken);
                         return;
                     }
+
                     await WriteChunkedAsync(data, cancellationToken);
                 }
                 else
@@ -599,7 +615,7 @@ namespace Microsoft.AspNetCore.Server.Kestrel.Internal.Http
             else
             {
                 HandleNonBodyResponseWrite();
-                return;
+                await FlushAsync(cancellationToken);
             }
         }
 
diff --git a/test/Microsoft.AspNetCore.Server.Kestrel.FunctionalTests/ResponseTests.cs b/test/Microsoft.AspNetCore.Server.Kestrel.FunctionalTests/ResponseTests.cs
index 5b4b5b73fe..dbf6f5bdd4 100644
--- a/test/Microsoft.AspNetCore.Server.Kestrel.FunctionalTests/ResponseTests.cs
+++ b/test/Microsoft.AspNetCore.Server.Kestrel.FunctionalTests/ResponseTests.cs
@@ -7,6 +7,7 @@ using System.Net;
 using System.Net.Http;
 using System.Net.Sockets;
 using System.Text;
+using System.Threading;
 using System.Threading.Tasks;
 using Microsoft.AspNetCore.Builder;
 using Microsoft.AspNetCore.Hosting;
@@ -767,11 +768,11 @@ namespace Microsoft.AspNetCore.Server.Kestrel.FunctionalTests
             {
                 using (var connection = server.CreateConnection())
                 {
-                    await connection.SendEnd(
+                    await connection.Send(
                         "HEAD / HTTP/1.1",
                         "",
                         "");
-                    await connection.ReceiveEnd(
+                    await connection.Receive(
                         "HTTP/1.1 200 OK",
                         $"Date: {server.Context.DateHeaderValue}",
                         "Content-Length: 42",
@@ -782,26 +783,95 @@ namespace Microsoft.AspNetCore.Server.Kestrel.FunctionalTests
         }
 
         [Fact]
-        public async Task HeadResponseCanContainContentLengthHeaderButBodyNotWritten()
+        public async Task HeadResponseBodyNotWrittenWithAsyncWrite()
         {
+            var flushed = new SemaphoreSlim(0, 1);
+
             using (var server = new TestServer(async httpContext =>
             {
                 httpContext.Response.ContentLength = 12;
                 await httpContext.Response.WriteAsync("hello, world");
+                await flushed.WaitAsync();
+            }, new TestServiceContext()))
+            {
+                using (var connection = server.CreateConnection())
+                {
+                    await connection.Send(
+                        "HEAD / HTTP/1.1",
+                        "",
+                        "");
+                    await connection.Receive(
+                        "HTTP/1.1 200 OK",
+                        $"Date: {server.Context.DateHeaderValue}",
+                        "Content-Length: 12",
+                        "",
+                        "");
+
+                    flushed.Release();
+                }
+            }
+        }
+
+        [Fact]
+        public async Task HeadResponseBodyNotWrittenWithSyncWrite()
+        {
+            var flushed = new SemaphoreSlim(0, 1);
+
+            using (var server = new TestServer(httpContext =>
+            {
+                httpContext.Response.ContentLength = 12;
+                httpContext.Response.Body.Write(Encoding.ASCII.GetBytes("hello, world"), 0, 12);
+                flushed.Wait();
+                return TaskCache.CompletedTask;
+            }, new TestServiceContext()))
+            {
+                using (var connection = server.CreateConnection())
+                {
+                    await connection.Send(
+                        "HEAD / HTTP/1.1",
+                        "",
+                        "");
+                    await connection.Receive(
+                        "HTTP/1.1 200 OK",
+                        $"Date: {server.Context.DateHeaderValue}",
+                        "Content-Length: 12",
+                        "",
+                        "");
+
+                    flushed.Release();
+                }
+            }
+        }
+
+        [Fact]
+        public async Task ZeroLengthWritesFlushHeaders()
+        {
+            var flushed = new SemaphoreSlim(0, 1);
+
+            using (var server = new TestServer(async httpContext =>
+            {
+                httpContext.Response.ContentLength = 12;
+                await httpContext.Response.WriteAsync("");
+                flushed.Wait();
+                await httpContext.Response.WriteAsync("hello, world");
             }, new TestServiceContext()))
             {
                 using (var connection = server.CreateConnection())
                 {
                     await connection.SendEnd(
-                        "HEAD / HTTP/1.1",
+                        "GET / HTTP/1.1",
                         "",
                         "");
-                    await connection.ReceiveEnd(
+                    await connection.Receive(
                         "HTTP/1.1 200 OK",
                         $"Date: {server.Context.DateHeaderValue}",
                         "Content-Length: 12",
                         "",
                         "");
+
+                    flushed.Release();
+
+                    await connection.ReceiveEnd("hello, world");
                 }
             }
         }
diff --git a/test/Microsoft.AspNetCore.Server.KestrelTests/ChunkedResponseTests.cs b/test/Microsoft.AspNetCore.Server.KestrelTests/ChunkedResponseTests.cs
index 469f17051c..7ce2297b00 100644
--- a/test/Microsoft.AspNetCore.Server.KestrelTests/ChunkedResponseTests.cs
+++ b/test/Microsoft.AspNetCore.Server.KestrelTests/ChunkedResponseTests.cs
@@ -192,6 +192,48 @@ namespace Microsoft.AspNetCore.Server.KestrelTests
             }
         }
 
+        [Theory]
+        [MemberData(nameof(ConnectionFilterData))]
+        public async Task ZeroLengthWritesFlushHeaders(TestServiceContext testContext)
+        {
+            var flushed = new SemaphoreSlim(0, 1);
+
+            using (var server = new TestServer(async httpContext =>
+            {
+                var response = httpContext.Response;
+                await response.WriteAsync("");
+
+                await flushed.WaitAsync();
+
+                await response.WriteAsync("Hello World!");
+            }, testContext))
+            {
+                using (var connection = server.CreateConnection())
+                {
+                    await connection.SendEnd(
+                        "GET / HTTP/1.1",
+                        "",
+                        "");
+
+                    await connection.Receive(
+                        "HTTP/1.1 200 OK",
+                        $"Date: {testContext.DateHeaderValue}",
+                        "Transfer-Encoding: chunked",
+                        "",
+                        "");
+
+                    flushed.Release();
+
+                    await connection.ReceiveEnd(
+                        "c",
+                        "Hello World!",
+                        "0",
+                        "",
+                        "");
+                }
+            }
+        }
+
         [Theory]
         [MemberData(nameof(ConnectionFilterData))]
         public async Task EmptyResponseBodyHandledCorrectlyWithZeroLengthWrite(TestServiceContext testContext)