diff --git a/jetty-server/src/main/java/org/eclipse/jetty/server/ResourceService.java b/jetty-server/src/main/java/org/eclipse/jetty/server/ResourceService.java
index 35f764da383..c007ab71c60 100644
--- a/jetty-server/src/main/java/org/eclipse/jetty/server/ResourceService.java
+++ b/jetty-server/src/main/java/org/eclipse/jetty/server/ResourceService.java
@@ -578,7 +578,7 @@ public class ResourceService
             {
                 //Get jetty's Response impl
                 String mdlm = content.getLastModifiedValue();
-                if (mdlm != null && ifms.equals(mdlm))
+                if (ifms.equals(mdlm))
                 {
                     sendStatus(response, HttpServletResponse.SC_NOT_MODIFIED, content::getETagValue);
                     return false;
@@ -676,17 +676,17 @@ public class ResourceService
                 writeContent(content, out, 0, content_length);
             }
             // else if we can't do a bypass write because of wrapping
-            else if (written || !(out instanceof HttpOutput))
+            else if (written)
             {
                 // write normally
-                putHeaders(response, content, written ? -1 : 0);
+                putHeaders(response, content, Response.NO_CONTENT_LENGTH);
                 writeContent(content, out, 0, content_length);
             }
             // else do a bypass write
             else
             {
                 // write the headers
-                putHeaders(response, content, 0);
+                putHeaders(response, content, Response.USE_KNOWN_CONTENT_LENGTH);
 
                 // write the content asynchronously if supported
                 if (request.isAsyncSupported() && content.getContentLengthValue() > response.getBufferSize())
@@ -735,7 +735,7 @@ public class ResourceService
             //  if there are no satisfiable ranges, send 416 response
             if (ranges == null || ranges.size() == 0)
             {
-                putHeaders(response, content, 0);
+                putHeaders(response, content, Response.USE_KNOWN_CONTENT_LENGTH);
                 response.setHeader(HttpHeader.CONTENT_RANGE.asString(),
                     InclusiveByteRange.to416HeaderRangeString(content_length));
                 sendStatus(response, HttpServletResponse.SC_REQUESTED_RANGE_NOT_SATISFIABLE, null);
@@ -762,8 +762,8 @@ public class ResourceService
             //  216 response which does not require an overall
             //  content-length header
             //
-            putHeaders(response, content, -1);
-            String mimetype = (content == null ? null : content.getContentTypeValue());
+            putHeaders(response, content, Response.NO_CONTENT_LENGTH);
+            String mimetype = content.getContentTypeValue();
             if (mimetype == null)
                 LOG.warn("Unknown mimetype for {}", request.getRequestURI());
             response.setStatus(HttpServletResponse.SC_PARTIAL_CONTENT);
diff --git a/jetty-server/src/main/java/org/eclipse/jetty/server/Response.java b/jetty-server/src/main/java/org/eclipse/jetty/server/Response.java
index f46126a1a8b..4a3e65bee7d 100644
--- a/jetty-server/src/main/java/org/eclipse/jetty/server/Response.java
+++ b/jetty-server/src/main/java/org/eclipse/jetty/server/Response.java
@@ -70,6 +70,8 @@ public class Response implements HttpServletResponse
 {
     private static final int __MIN_BUFFER_SIZE = 1;
     private static final HttpField __EXPIRES_01JAN1970 = new PreEncodedHttpField(HttpHeader.EXPIRES, DateGenerator.__01Jan1970);
+    public static final int NO_CONTENT_LENGTH = -1;
+    public static final int USE_KNOWN_CONTENT_LENGTH = -2;
 
     public enum OutputType
     {
@@ -1339,12 +1341,12 @@ public class Response implements HttpServletResponse
         if (lm != null)
             _fields.put(lm);
 
-        if (contentLength == 0)
+        if (contentLength == USE_KNOWN_CONTENT_LENGTH)
         {
             _fields.put(content.getContentLength());
             _contentLength = content.getContentLengthValue();
         }
-        else if (contentLength > 0)
+        else if (contentLength > NO_CONTENT_LENGTH)
         {
             _fields.putLongField(HttpHeader.CONTENT_LENGTH, contentLength);
             _contentLength = contentLength;
@@ -1387,9 +1389,9 @@ public class Response implements HttpServletResponse
         if (lml >= 0)
             response.setDateHeader(HttpHeader.LAST_MODIFIED.asString(), lml);
 
-        if (contentLength == 0)
+        if (contentLength == USE_KNOWN_CONTENT_LENGTH)
             contentLength = content.getContentLengthValue();
-        if (contentLength >= 0)
+        if (contentLength > NO_CONTENT_LENGTH)
         {
             if (contentLength < Integer.MAX_VALUE)
                 response.setContentLength((int)contentLength);
diff --git a/jetty-servlet/src/main/java/org/eclipse/jetty/servlet/DefaultServlet.java b/jetty-servlet/src/main/java/org/eclipse/jetty/servlet/DefaultServlet.java
index 2be9f6c928d..e704b6f0646 100644
--- a/jetty-servlet/src/main/java/org/eclipse/jetty/servlet/DefaultServlet.java
+++ b/jetty-servlet/src/main/java/org/eclipse/jetty/servlet/DefaultServlet.java
@@ -464,16 +464,24 @@ public class DefaultServlet extends HttpServlet implements ResourceFactory, Welc
     }
 
     @Override
-    protected void doTrace(HttpServletRequest req, HttpServletResponse resp) throws ServletException, IOException
+    protected void doHead(HttpServletRequest request, HttpServletResponse response)
+        throws ServletException, IOException
     {
-        resp.sendError(HttpServletResponse.SC_METHOD_NOT_ALLOWED);
+        doGet(request, response);
     }
 
     @Override
-    protected void doOptions(HttpServletRequest req, HttpServletResponse resp)
+    protected void doTrace(HttpServletRequest request, HttpServletResponse response)
         throws ServletException, IOException
     {
-        resp.setHeader("Allow", "GET,HEAD,POST,OPTIONS");
+        response.sendError(HttpServletResponse.SC_METHOD_NOT_ALLOWED);
+    }
+
+    @Override
+    protected void doOptions(HttpServletRequest request, HttpServletResponse response)
+        throws ServletException, IOException
+    {
+        response.setHeader("Allow", "GET,HEAD,POST,OPTIONS");
     }
 
     @Override
diff --git a/jetty-webapp/src/test/java/org/eclipse/jetty/webapp/HugeResourceTest.java b/jetty-webapp/src/test/java/org/eclipse/jetty/webapp/HugeResourceTest.java
index 7bb613c79c5..f0ad5ab295c 100644
--- a/jetty-webapp/src/test/java/org/eclipse/jetty/webapp/HugeResourceTest.java
+++ b/jetty-webapp/src/test/java/org/eclipse/jetty/webapp/HugeResourceTest.java
@@ -238,6 +238,31 @@ public class HugeResourceTest
         }
     }
 
+    @ParameterizedTest
+    @MethodSource("staticFiles")
+    public void testHead(String filename, long expectedSize) throws Exception
+    {
+        URI destUri = server.getURI().resolve("/" + filename);
+        InputStreamResponseListener responseListener = new InputStreamResponseListener();
+
+        Request request = client.newRequest(destUri)
+            .method(HttpMethod.HEAD);
+        request.send(responseListener);
+        Response response = responseListener.get(5, TimeUnit.SECONDS);
+
+        try (InputStream in = responseListener.getInputStream())
+        {
+            assertThat(in.read(), is(-1));
+        }
+
+        assertThat("HTTP Response Code", response.getStatus(), is(200));
+        // dumpResponse(response);
+
+        String contentLength = response.getHeaders().get(HttpHeader.CONTENT_LENGTH);
+        long contentLengthLong = Long.parseLong(contentLength);
+        assertThat("Http Response Header: \"Content-Length: " + contentLength + "\"", contentLengthLong, is(expectedSize));
+    }
+
     @ParameterizedTest
     @MethodSource("staticFiles")
     public void testUpload(String filename, long expectedSize) throws Exception