diff --git a/Lib/test/regrtest.py b/Lib/test/regrtest.py
index 214e430e059..ca63496bf8a 100755
--- a/Lib/test/regrtest.py
+++ b/Lib/test/regrtest.py
@@ -577,7 +577,6 @@ def main(tests=None, testdir=None, verbose=0, quiet=False,
         elif ok == FAILED:
             bad.append(test)
         elif ok == ENV_CHANGED:
-            bad.append(test)
             environment_changed.append(test)
         elif ok == SKIPPED:
             skipped.append(test)
diff --git a/Lib/test/test_multiprocessing.py b/Lib/test/test_multiprocessing.py
index 405fbd52569..7a7805d59f6 100644
--- a/Lib/test/test_multiprocessing.py
+++ b/Lib/test/test_multiprocessing.py
@@ -35,7 +35,7 @@ import multiprocessing.managers
 import multiprocessing.heap
 import multiprocessing.pool
 
-from multiprocessing import util
+from multiprocessing import util, reduction
 
 try:
     from multiprocessing.sharedctypes import Value, copy
@@ -43,6 +43,11 @@ try:
 except ImportError:
     HAS_SHAREDCTYPES = False
 
+try:
+    import msvcrt
+except ImportError:
+    msvcrt = None
+
 #
 #
 #
@@ -89,6 +94,11 @@ else:
             timeout = None
         return handle in _select([handle], [], [], timeout)[0]
 
+try:
+    MAXFD = os.sysconf("SC_OPEN_MAX")
+except:
+    MAXFD = 256
+
 #
 # Some tests require ctypes
 #
@@ -1587,6 +1597,76 @@ class _TestConnection(BaseTestCase):
 
         self.assertRaises(ValueError, a.send_bytes, msg, 4, -1)
 
+    @classmethod
+    def _is_fd_assigned(cls, fd):
+        try:
+            os.fstat(fd)
+        except OSError as e:
+            if e.errno == errno.EBADF:
+                return False
+            raise
+        else:
+            return True
+
+    @classmethod
+    def _writefd(cls, conn, data, create_dummy_fds=False):
+        if create_dummy_fds:
+            for i in range(0, 256):
+                if not cls._is_fd_assigned(i):
+                    os.dup2(conn.fileno(), i)
+        fd = reduction.recv_handle(conn)
+        if msvcrt:
+            fd = msvcrt.open_osfhandle(fd, os.O_WRONLY)
+        os.write(fd, data)
+        os.close(fd)
+
+    def test_fd_transfer(self):
+        if self.TYPE != 'processes':
+            self.skipTest("only makes sense with processes")
+        conn, child_conn = self.Pipe(duplex=True)
+
+        p = self.Process(target=self._writefd, args=(child_conn, b"foo"))
+        p.start()
+        with open(test.support.TESTFN, "wb") as f:
+            fd = f.fileno()
+            if msvcrt:
+                fd = msvcrt.get_osfhandle(fd)
+            reduction.send_handle(conn, fd, p.pid)
+        p.join()
+        with open(test.support.TESTFN, "rb") as f:
+            self.assertEqual(f.read(), b"foo")
+
+    @unittest.skipIf(sys.platform == "win32",
+                     "test semantics don't make sense on Windows")
+    @unittest.skipIf(MAXFD <= 256,
+                     "largest assignable fd number is too small")
+    @unittest.skipUnless(hasattr(os, "dup2"),
+                         "test needs os.dup2()")
+    def test_large_fd_transfer(self):
+        # With fd > 256 (issue #11657)
+        if self.TYPE != 'processes':
+            self.skipTest("only makes sense with processes")
+        conn, child_conn = self.Pipe(duplex=True)
+
+        p = self.Process(target=self._writefd, args=(child_conn, b"bar", True))
+        p.start()
+        with open(test.support.TESTFN, "wb") as f:
+            fd = f.fileno()
+            for newfd in range(256, MAXFD):
+                if not self._is_fd_assigned(newfd):
+                    break
+            else:
+                self.fail("could not find an unassigned large file descriptor")
+            os.dup2(fd, newfd)
+            try:
+                reduction.send_handle(conn, newfd, p.pid)
+            finally:
+                os.close(newfd)
+        p.join()
+        with open(test.support.TESTFN, "rb") as f:
+            self.assertEqual(f.read(), b"bar")
+
+
 class _TestListenerClient(BaseTestCase):
 
     ALLOWED_TYPES = ('processes', 'threads')
diff --git a/Misc/NEWS b/Misc/NEWS
index b2d9e84b943..4b5a9a6d778 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -268,6 +268,9 @@ Core and Builtins
 Library
 -------
 
+- Issue #11657: Fix sending file descriptors over 255 over a multiprocessing
+  Pipe.
+
 - Issue #12811: tabnanny.check() now promptly closes checked files. Patch by
   Anthony Briggs.
 
diff --git a/Modules/_multiprocessing/multiprocessing.c b/Modules/_multiprocessing/multiprocessing.c
index 5d1cf5661aa..1987b951f94 100644
--- a/Modules/_multiprocessing/multiprocessing.c
+++ b/Modules/_multiprocessing/multiprocessing.c
@@ -111,7 +111,7 @@ multiprocessing_sendfd(PyObject *self, PyObject *args)
     cmsg->cmsg_type = SCM_RIGHTS;
     cmsg->cmsg_len = CMSG_LEN(sizeof(int));
     msg.msg_controllen = cmsg->cmsg_len;
-    *CMSG_DATA(cmsg) = fd;
+    * (int *) CMSG_DATA(cmsg) = fd;
 
     Py_BEGIN_ALLOW_THREADS
     res = sendmsg(conn, &msg, 0);
@@ -154,7 +154,7 @@ multiprocessing_recvfd(PyObject *self, PyObject *args)
     if (res < 0)
         return PyErr_SetFromErrno(PyExc_OSError);
 
-    fd = *CMSG_DATA(cmsg);
+    fd = * (int *) CMSG_DATA(cmsg);
     return Py_BuildValue("i", fd);
 }