diff --git a/src/Microsoft.Net.Http.Server/RequestProcessing/Response.cs b/src/Microsoft.Net.Http.Server/RequestProcessing/Response.cs
index a16d11f..7185d03 100644
--- a/src/Microsoft.Net.Http.Server/RequestProcessing/Response.cs
+++ b/src/Microsoft.Net.Http.Server/RequestProcessing/Response.cs
@@ -453,14 +453,14 @@ namespace Microsoft.Net.Http.Server
                 _boundaryType = BoundaryType.ContentLength;
                 _expectedBodyLength = 0;
             }
-            else if (keepConnectionAlive && requestVersion == Constants.V1_1)
+            else if (requestVersion == Constants.V1_1)
             {
                 _boundaryType = BoundaryType.Chunked;
                 Headers[HttpKnownHeaderNames.TransferEncoding] = Constants.Chunked;
             }
             else
             {
-                // The length cannot be determined, so we must close the connection
+                // v1.0 and the length cannot be determined, so we must close the connection after writing data
                 keepConnectionAlive = false;
                 _boundaryType = BoundaryType.Close;
             }
diff --git a/test/Microsoft.AspNetCore.Server.WebListener.FunctionalTests/ResponseHeaderTests.cs b/test/Microsoft.AspNetCore.Server.WebListener.FunctionalTests/ResponseHeaderTests.cs
index b5f7ba1..8183b52 100644
--- a/test/Microsoft.AspNetCore.Server.WebListener.FunctionalTests/ResponseHeaderTests.cs
+++ b/test/Microsoft.AspNetCore.Server.WebListener.FunctionalTests/ResponseHeaderTests.cs
@@ -133,7 +133,8 @@ namespace Microsoft.AspNetCore.Server.WebListener
                 response.EnsureSuccessStatusCode();
                 Assert.True(response.Headers.ConnectionClose.Value);
                 Assert.Equal(new string[] { "close" }, response.Headers.GetValues("Connection"));
-                Assert.False(response.Headers.TransferEncodingChunked.HasValue);
+                Assert.True(response.Headers.TransferEncodingChunked.HasValue);
+                Assert.True(response.Headers.TransferEncodingChunked);
                 IEnumerable<string> values;
                 var result = response.Content.Headers.TryGetValues("Content-Length", out values);
                 Assert.False(result);