diff --git a/Doc/library/httplib.rst b/Doc/library/httplib.rst
index 354edb234df..a4bff4f230a 100644
--- a/Doc/library/httplib.rst
+++ b/Doc/library/httplib.rst
@@ -433,9 +433,16 @@ HTTPConnection Objects
    and the selector *url*.  If the *body* argument is present, it should be a
    string of data to send after the headers are finished. Alternatively, it may
    be an open file object, in which case the contents of the file is sent; this
-   file object should support ``fileno()`` and ``read()`` methods. The header
-   Content-Length is automatically set to the correct value. The *headers*
-   argument should be a mapping of extra HTTP headers to send with the request.
+   file object should support ``fileno()`` and ``read()`` methods. The
+   *headers* argument should be a mapping of extra HTTP headers to send with
+   the request.
+
+   If one is not provided in *headers*, a ``Content-Length`` header is added
+   automatically for all methods if the length of the body can be determined,
+   either from the length of the ``str`` representation, or from the reported
+   size of the file on disk. If *body* is ``None`` the header is not set except
+   for methods that expect a body (``PUT``, ``POST``, and ``PATCH``) in which
+   case it is set to ``0``.
 
    .. versionchanged:: 2.6
       *body* can be a file object.
diff --git a/Lib/httplib.py b/Lib/httplib.py
index 30466ca5302..5406e77d4d1 100644
--- a/Lib/httplib.py
+++ b/Lib/httplib.py
@@ -247,6 +247,10 @@ _MAXHEADERS = 100
 _is_legal_header_name = re.compile(r'\A[^:\s][^:\r\n]*\Z').match
 _is_illegal_header_value = re.compile(r'\n(?![ \t])|\r(?![ \t\n])').search
 
+# We always set the Content-Length header for these methods because some
+# servers will otherwise respond with a 411
+_METHODS_EXPECTING_BODY = {'PATCH', 'POST', 'PUT'}
+
 
 class HTTPMessage(mimetools.Message):
 
@@ -1043,19 +1047,25 @@ class HTTPConnection:
         """Send a complete request to the server."""
         self._send_request(method, url, body, headers)
 
-    def _set_content_length(self, body):
-        # Set the content-length based on the body.
+    def _set_content_length(self, body, method):
+        # Set the content-length based on the body. If the body is "empty", we
+        # set Content-Length: 0 for methods that expect a body (RFC 7230,
+        # Section 3.3.2). If the body is set for other methods, we set the
+        # header provided we can figure out what the length is.
         thelen = None
-        try:
-            thelen = str(len(body))
-        except TypeError, te:
-            # If this is a file-like object, try to
-            # fstat its file descriptor
+        if body is None and method.upper() in _METHODS_EXPECTING_BODY:
+            thelen = '0'
+        elif body is not None:
             try:
-                thelen = str(os.fstat(body.fileno()).st_size)
-            except (AttributeError, OSError):
-                # Don't send a length if this failed
-                if self.debuglevel > 0: print "Cannot stat!!"
+                thelen = str(len(body))
+            except TypeError:
+                # If this is a file-like object, try to
+                # fstat its file descriptor
+                try:
+                    thelen = str(os.fstat(body.fileno()).st_size)
+                except (AttributeError, OSError):
+                    # Don't send a length if this failed
+                    if self.debuglevel > 0: print "Cannot stat!!"
 
         if thelen is not None:
             self.putheader('Content-Length', thelen)
@@ -1071,8 +1081,8 @@ class HTTPConnection:
 
         self.putrequest(method, url, **skips)
 
-        if body is not None and 'content-length' not in header_names:
-            self._set_content_length(body)
+        if 'content-length' not in header_names:
+            self._set_content_length(body, method)
         for hdr, value in headers.iteritems():
             self.putheader(hdr, value)
         self.endheaders(body)
diff --git a/Lib/test/test_httplib.py b/Lib/test/test_httplib.py
index 29614e39dbf..fc7c5710e46 100644
--- a/Lib/test/test_httplib.py
+++ b/Lib/test/test_httplib.py
@@ -1,4 +1,5 @@
 import httplib
+import itertools
 import array
 import StringIO
 import socket
@@ -122,21 +123,59 @@ class HeaderTests(TestCase):
                     self.content_length = kv[1].strip()
                 list.append(self, item)
 
-        # POST with empty body
-        conn = httplib.HTTPConnection('example.com')
-        conn.sock = FakeSocket(None)
-        conn._buffer = ContentLengthChecker()
-        conn.request('POST', '/', '')
-        self.assertEqual(conn._buffer.content_length, '0',
-                        'Header Content-Length not set')
+        # Here, we're testing that methods expecting a body get a
+        # content-length set to zero if the body is empty (either None or '')
+        bodies = (None, '')
+        methods_with_body = ('PUT', 'POST', 'PATCH')
+        for method, body in itertools.product(methods_with_body, bodies):
+            conn = httplib.HTTPConnection('example.com')
+            conn.sock = FakeSocket(None)
+            conn._buffer = ContentLengthChecker()
+            conn.request(method, '/', body)
+            self.assertEqual(
+                conn._buffer.content_length, '0',
+                'Header Content-Length incorrect on {}'.format(method)
+            )
 
-        # PUT request with empty body
-        conn = httplib.HTTPConnection('example.com')
-        conn.sock = FakeSocket(None)
-        conn._buffer = ContentLengthChecker()
-        conn.request('PUT', '/', '')
-        self.assertEqual(conn._buffer.content_length, '0',
-                        'Header Content-Length not set')
+        # For these methods, we make sure that content-length is not set when
+        # the body is None because it might cause unexpected behaviour on the
+        # server.
+        methods_without_body = (
+             'GET', 'CONNECT', 'DELETE', 'HEAD', 'OPTIONS', 'TRACE',
+        )
+        for method in methods_without_body:
+            conn = httplib.HTTPConnection('example.com')
+            conn.sock = FakeSocket(None)
+            conn._buffer = ContentLengthChecker()
+            conn.request(method, '/', None)
+            self.assertEqual(
+                conn._buffer.content_length, None,
+                'Header Content-Length set for empty body on {}'.format(method)
+            )
+
+        # If the body is set to '', that's considered to be "present but
+        # empty" rather than "missing", so content length would be set, even
+        # for methods that don't expect a body.
+        for method in methods_without_body:
+            conn = httplib.HTTPConnection('example.com')
+            conn.sock = FakeSocket(None)
+            conn._buffer = ContentLengthChecker()
+            conn.request(method, '/', '')
+            self.assertEqual(
+                conn._buffer.content_length, '0',
+                'Header Content-Length incorrect on {}'.format(method)
+            )
+
+        # If the body is set, make sure Content-Length is set.
+        for method in itertools.chain(methods_without_body, methods_with_body):
+            conn = httplib.HTTPConnection('example.com')
+            conn.sock = FakeSocket(None)
+            conn._buffer = ContentLengthChecker()
+            conn.request(method, '/', ' ')
+            self.assertEqual(
+                conn._buffer.content_length, '1',
+                'Header Content-Length incorrect on {}'.format(method)
+            )
 
     def test_putheader(self):
         conn = httplib.HTTPConnection('example.com')
diff --git a/Misc/ACKS b/Misc/ACKS
index 752b83a8972..8b29171475e 100644
--- a/Misc/ACKS
+++ b/Misc/ACKS
@@ -1171,6 +1171,7 @@ Sam Rushing
 Mark Russell
 Rusty Russell
 Nick Russo
+James Rutherford
 Chris Ryland
 Constantina S.
 Patrick Sabin
diff --git a/Misc/NEWS b/Misc/NEWS
index 70a882e9609..111a2801cbf 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -21,6 +21,10 @@ Core and Builtins
 Library
 -------
 
+- Issue #23539: If body is None, http.client.HTTPConnection.request now sets
+  Content-Length to 0 for PUT, POST, and PATCH headers to avoid 411 errors from
+  some web servers.
+
 - Issue #23136: _strptime now uniformly handles all days in week 0, including
   Dec 30 of previous year.  Based on patch by Jim Carroll.