diff --git a/Lib/http/server.py b/Lib/http/server.py
--- a/Lib/http/server.py
+++ b/Lib/http/server.py
@@ -425,12 +425,14 @@ class BaseHTTPRequestHandler(socketserve
         # using _quote_html to prevent Cross Site Scripting attacks (see bug #1100201)
         content = (self.error_message_format %
                    {'code': code, 'message': _quote_html(message), 'explain': explain})
+        body = content.encode('UTF-8', 'replace')
         self.send_response(code, message)
         self.send_header("Content-Type", self.error_content_type)
         self.send_header('Connection', 'close')
+        self.send_header('Content-Length', int(len(body)))
         self.end_headers()
         if self.command != 'HEAD' and code >= 200 and code not in (204, 304):
-            self.wfile.write(content.encode('UTF-8', 'replace'))
+            self.wfile.write(body)
 
     def send_response(self, code, message=None):
         """Add the response header to the headers buffer and log the
diff --git a/Lib/test/test_httpservers.py b/Lib/test/test_httpservers.py
--- a/Lib/test/test_httpservers.py
+++ b/Lib/test/test_httpservers.py
@@ -91,6 +91,9 @@ class BaseHTTPServerTestCase(BaseTestCas
         def do_KEYERROR(self):
             self.send_error(999)
 
+        def do_NOTFOUND(self):
+            self.send_error(404)
+
         def do_CUSTOM(self):
             self.send_response(999)
             self.send_header('Content-Type', 'text/html')
@@ -210,6 +213,14 @@ class BaseHTTPServerTestCase(BaseTestCas
         self.assertEqual(res.getheader('X-Special'), 'Dängerous Mind')
         self.assertEqual(res.read(), 'Ärger mit Unicode'.encode('utf-8'))
 
+    def test_error_content_length(self):
+        # Issue #16088: standard error responses should have a content-length
+        self.con.request('NOTFOUND', '/')
+        res = self.con.getresponse()
+        self.assertEqual(res.status, 404)
+        data = res.read()
+        self.assertEqual(int(res.getheader('Content-Length')), len(data))
+
 
 class SimpleHTTPServerTestCase(BaseTestCase):
     class request_handler(NoLogRequestHandler, SimpleHTTPRequestHandler):