diff --git a/Lib/socket.py b/Lib/socket.py
index 3073c012b19..c8de9896131 100644
--- a/Lib/socket.py
+++ b/Lib/socket.py
@@ -58,6 +58,13 @@
 from enum import IntEnum, IntFlag
 from functools import partial
 
+try:
+    import _overlapped
+    import msvcrt
+except ImportError:
+    _overlapped = None
+    msvcrt = None
+
 try:
     import errno
 except ImportError:
@@ -467,6 +474,39 @@ def _sendfile_use_send(self, file, offset=0, count=None):
             if total_sent > 0 and hasattr(file, 'seek'):
                 file.seek(offset + total_sent)
 
+    if _overlapped and msvcrt:
+        def _sendfile_use_transmitfile(self, file, offset=0, count=None):
+            self._check_sendfile_params(file, offset, count)
+            timeout = self.gettimeout()
+            if timeout == 0:
+                raise ValueError("non-blocking sockets are not supported")
+            ov = _overlapped.Overlapped()
+            offset_low = offset & 0xffff_ffff
+            offset_high = (offset >> 32) & 0xffff_ffff
+            count = count or 0
+            try:
+                fileno = file.fileno()
+            except (AttributeError, io.UnsupportedOperation) as err:
+                raise _GiveupOnSendfile(err)  # not a regular file
+            try:
+                os.fstat(fileno)
+            except OSError as err:
+                raise _GiveupOnSendfile(err)  # not a regular file
+            ov.TransmitFile(self.fileno(), msvcrt.get_osfhandle(fileno),
+                            offset_low, offset_high, count, 0, 0)
+            timeout_ms = _overlapped.INFINITE
+            if timeout is not None:
+                timeout_ms = int(timeout * 1000)
+            try:
+                sent = ov.getresultex(timeout_ms, False)
+            except WindowsError as e:
+                if e.winerror == 258:
+                    raise TimeoutError('timed out')
+                raise
+            if sent > 0 and hasattr(file, 'seek'):
+                file.seek(offset + sent)
+            return sent
+
     def _check_sendfile_params(self, file, offset, count):
         if 'b' not in getattr(file, 'mode', 'b'):
             raise ValueError("file should be opened in binary mode")
@@ -499,6 +539,8 @@ def sendfile(self, file, offset=0, count=None):
         Non-blocking sockets are not supported.
         """
         try:
+            if sys.platform == "win32":
+                return self._sendfile_use_transmitfile(file, offset, count)
             return self._sendfile_use_sendfile(file, offset, count)
         except _GiveupOnSendfile:
             return self._sendfile_use_send(file, offset, count)
diff --git a/Lib/test/test_socket.py b/Lib/test/test_socket.py
index 934b7137096..037ba87c192 100644
--- a/Lib/test/test_socket.py
+++ b/Lib/test/test_socket.py
@@ -7055,6 +7055,15 @@ def meth_from_sock(self, sock):
         return getattr(sock, "_sendfile_use_sendfile")
 
 
+@unittest.skipUnless(sys.platform == "win32", "Windows only test.")
+class SendfileUsingTransmitfileTest(SendfileUsingSendTest):
+    """
+    Test the TransmitFile() implementation of socket.sendfile().
+    """
+    def meth_from_sock(self, sock):
+        return getattr(sock, "_sendfile_use_transmitfile")
+
+
 @unittest.skipUnless(HAVE_SOCKET_ALG, 'AF_ALG required')
 class LinuxKernelCryptoAPI(unittest.TestCase):
     # tests for AF_ALG
diff --git a/Misc/NEWS.d/next/Windows/2023-11-23-22-25-16.gh-issue-65920.6wWsHN.rst b/Misc/NEWS.d/next/Windows/2023-11-23-22-25-16.gh-issue-65920.6wWsHN.rst
new file mode 100644
index 00000000000..890f816013f
--- /dev/null
+++ b/Misc/NEWS.d/next/Windows/2023-11-23-22-25-16.gh-issue-65920.6wWsHN.rst
@@ -0,0 +1 @@
+Use :c:func:`!TransmitFile` on Windows to implement :func:`socket.sendfile`.
diff --git a/Modules/clinic/overlapped.c.h b/Modules/clinic/overlapped.c.h
index 7e2480bdace..90743a1b0b6 100644
--- a/Modules/clinic/overlapped.c.h
+++ b/Modules/clinic/overlapped.c.h
@@ -561,6 +561,41 @@ exit:
     return return_value;
 }
 
+PyDoc_STRVAR(_overlapped_Overlapped_getresultex__doc__,
+"getresultex($self, milliseconds, alertable, /)\n"
+"--\n"
+"\n");
+
+#define _OVERLAPPED_OVERLAPPED_GETRESULTEX_METHODDEF    \
+    {"getresultex", _PyCFunction_CAST(_overlapped_Overlapped_getresultex), METH_FASTCALL, _overlapped_Overlapped_getresultex__doc__},
+
+static PyObject *
+_overlapped_Overlapped_getresultex_impl(OverlappedObject *self,
+                                        DWORD milliseconds, BOOL alertable);
+
+static PyObject *
+_overlapped_Overlapped_getresultex(OverlappedObject *self, PyObject *const *args, Py_ssize_t nargs)
+{
+    PyObject *return_value = NULL;
+    DWORD milliseconds;
+    BOOL alertable;
+
+    if (!_PyArg_CheckPositional("getresultex", nargs, 2, 2)) {
+        goto exit;
+    }
+    if (!_PyLong_UnsignedLong_Converter(args[0], &milliseconds)) {
+        goto exit;
+    }
+    alertable = PyLong_AsInt(args[1]);
+    if (alertable == -1 && PyErr_Occurred()) {
+        goto exit;
+    }
+    return_value = _overlapped_Overlapped_getresultex_impl(self, milliseconds, alertable);
+
+exit:
+    return return_value;
+}
+
 PyDoc_STRVAR(_overlapped_Overlapped_ReadFile__doc__,
 "ReadFile($self, handle, size, /)\n"
 "--\n"
diff --git a/Modules/overlapped.c b/Modules/overlapped.c
index 29b7b356648..50a7238ec6c 100644
--- a/Modules/overlapped.c
+++ b/Modules/overlapped.c
@@ -876,44 +876,13 @@ _overlapped_Overlapped_cancel_impl(OverlappedObject *self)
     Py_RETURN_NONE;
 }
 
-/*[clinic input]
-_overlapped.Overlapped.getresult
-
-    wait: BOOL(c_default='FALSE') = False
-    /
-
-Retrieve result of operation.
-
-If wait is true then it blocks until the operation is finished.  If wait
-is false and the operation is still pending then an error is raised.
-[clinic start generated code]*/
-
 static PyObject *
-_overlapped_Overlapped_getresult_impl(OverlappedObject *self, BOOL wait)
-/*[clinic end generated code: output=8c9bd04d08994f6c input=aa5b03e9897ca074]*/
+check_getresult_error(OverlappedObject *self, DWORD transferred)
 {
-    DWORD transferred = 0;
-    BOOL ret;
-    DWORD err;
-    PyObject *addr;
+    PyObject *addr = NULL;
+    DWORD err = self->error;
 
-    if (self->type == TYPE_NONE) {
-        PyErr_SetString(PyExc_ValueError, "operation not yet attempted");
-        return NULL;
-    }
-
-    if (self->type == TYPE_NOT_STARTED) {
-        PyErr_SetString(PyExc_ValueError, "operation failed to start");
-        return NULL;
-    }
-
-    Py_BEGIN_ALLOW_THREADS
-    ret = GetOverlappedResult(self->handle, &self->overlapped, &transferred,
-                              wait);
-    Py_END_ALLOW_THREADS
-
-    self->error = err = ret ? ERROR_SUCCESS : GetLastError();
-    switch (err) {
+    switch (self->error) {
         case ERROR_SUCCESS:
         case ERROR_MORE_DATA:
             break;
@@ -1005,6 +974,82 @@ _overlapped_Overlapped_getresult_impl(OverlappedObject *self, BOOL wait)
     }
 }
 
+/*[clinic input]
+_overlapped.Overlapped.getresult
+
+    wait: BOOL(c_default='FALSE') = False
+    /
+
+Retrieve result of operation.
+
+If wait is true then it blocks until the operation is finished.  If wait
+is false and the operation is still pending then an error is raised.
+[clinic start generated code]*/
+
+static PyObject *
+_overlapped_Overlapped_getresult_impl(OverlappedObject *self, BOOL wait)
+/*[clinic end generated code: output=8c9bd04d08994f6c input=aa5b03e9897ca074]*/
+{
+    DWORD transferred = 0;
+    BOOL ret;
+
+    if (self->type == TYPE_NONE) {
+        PyErr_SetString(PyExc_ValueError, "operation not yet attempted");
+        return NULL;
+    }
+
+    if (self->type == TYPE_NOT_STARTED) {
+        PyErr_SetString(PyExc_ValueError, "operation failed to start");
+        return NULL;
+    }
+
+    Py_BEGIN_ALLOW_THREADS
+    ret = GetOverlappedResult(self->handle, &self->overlapped, &transferred,
+                              wait);
+    Py_END_ALLOW_THREADS
+
+    self->error = ret ? ERROR_SUCCESS : GetLastError();
+
+    return check_getresult_error(self, transferred);
+}
+
+/*[clinic input]
+_overlapped.Overlapped.getresultex
+
+    milliseconds: DWORD
+    alertable: BOOL
+    /
+
+[clinic start generated code]*/
+
+static PyObject *
+_overlapped_Overlapped_getresultex_impl(OverlappedObject *self,
+                                        DWORD milliseconds, BOOL alertable)
+/*[clinic end generated code: output=ce0eb6ffb9618e54 input=ef4f4cab49ac1d80]*/
+{
+    DWORD transferred = 0;
+    BOOL ret;
+
+    if (self->type == TYPE_NONE) {
+        PyErr_SetString(PyExc_ValueError, "operation not yet attempted");
+        return NULL;
+    }
+
+    if (self->type == TYPE_NOT_STARTED) {
+        PyErr_SetString(PyExc_ValueError, "operation failed to start");
+        return NULL;
+    }
+
+    Py_BEGIN_ALLOW_THREADS
+    ret = GetOverlappedResultEx(self->handle, &self->overlapped, &transferred,
+                                milliseconds, alertable);
+    Py_END_ALLOW_THREADS
+
+    self->error = ret ? ERROR_SUCCESS : GetLastError();
+
+    return check_getresult_error(self, transferred);
+}
+
 static PyObject *
 do_ReadFile(OverlappedObject *self, HANDLE handle,
             char *bufstart, DWORD buflen)
@@ -1950,6 +1995,7 @@ _overlapped_Overlapped_WSARecvFromInto_impl(OverlappedObject *self,
 
 static PyMethodDef Overlapped_methods[] = {
     _OVERLAPPED_OVERLAPPED_GETRESULT_METHODDEF
+    _OVERLAPPED_OVERLAPPED_GETRESULTEX_METHODDEF
     _OVERLAPPED_OVERLAPPED_CANCEL_METHODDEF
     _OVERLAPPED_OVERLAPPED_READFILE_METHODDEF
     _OVERLAPPED_OVERLAPPED_READFILEINTO_METHODDEF