diff --git a/src/core/iomgr/socket_windows.c b/src/core/iomgr/socket_windows.c
index 91268c0..a622da9 100644
--- a/src/core/iomgr/socket_windows.c
+++ b/src/core/iomgr/socket_windows.c
@@ -32,11 +32,12 @@
  */
 
 #include <grpc/support/port_platform.h>
-#include <grpc/support/alloc.h>
-#include <grpc/support/log.h>
 
 #ifdef GPR_WINSOCK_SOCKET
 
+#include <grpc/support/alloc.h>
+#include <grpc/support/log.h>
+
 #include "src/core/iomgr/iocp_windows.h"
 #include "src/core/iomgr/iomgr.h"
 #include "src/core/iomgr/iomgr_internal.h"
@@ -64,16 +65,22 @@
   shutdown_op(&socket->write_info);
 }
 
-void grpc_winsocket_orphan(grpc_winsocket *socket) {
-  grpc_iocp_socket_orphan(socket);
-  socket->orphan = 1;
+void grpc_winsocket_orphan(grpc_winsocket *winsocket) {
+  SOCKET socket = winsocket->socket;
+  if (!winsocket->closed_early) {
+    grpc_iocp_socket_orphan(winsocket);
+    winsocket->orphan = 1;
+  }
   grpc_iomgr_unref();
-  closesocket(socket->socket);
+  if (winsocket->closed_early) {
+    grpc_winsocket_destroy(winsocket);
+  }
+  closesocket(socket);
 }
 
-void grpc_winsocket_destroy(grpc_winsocket *socket) {
-  gpr_mu_destroy(&socket->state_mu);
-  gpr_free(socket);
+void grpc_winsocket_destroy(grpc_winsocket *winsocket) {
+  gpr_mu_destroy(&winsocket->state_mu);
+  gpr_free(winsocket);
 }
 
 #endif  /* GPR_WINSOCK_SOCKET */
diff --git a/src/core/iomgr/socket_windows.h b/src/core/iomgr/socket_windows.h
index cbae916..ee09066 100644
--- a/src/core/iomgr/socket_windows.h
+++ b/src/core/iomgr/socket_windows.h
@@ -64,6 +64,7 @@
 
   int added_to_iocp;
   int orphan;
+  int closed_early;
 } grpc_winsocket;
 
 /* Create a wrapped windows handle.
diff --git a/src/core/iomgr/tcp_client_windows.c b/src/core/iomgr/tcp_client_windows.c
index 00c8da6..eee6320 100644
--- a/src/core/iomgr/tcp_client_windows.c
+++ b/src/core/iomgr/tcp_client_windows.c
@@ -115,6 +115,9 @@
 finish:
   gpr_mu_lock(&ac->mu);
   if (!ep) {
+    if (success) {
+      ac->socket->closed_early = 1;
+    }
     grpc_winsocket_orphan(ac->socket);
   }
   async_connect_cleanup(ac);
@@ -202,6 +205,7 @@
   gpr_log(GPR_ERROR, message, utf8_message);
   gpr_free(utf8_message);
   if (socket) {
+    socket->closed_early = 1;
     grpc_winsocket_orphan(socket);
   } else if (sock != INVALID_SOCKET) {
     closesocket(sock);
diff --git a/src/core/iomgr/tcp_server_windows.c b/src/core/iomgr/tcp_server_windows.c
index fe92846..a09c1ae 100644
--- a/src/core/iomgr/tcp_server_windows.c
+++ b/src/core/iomgr/tcp_server_windows.c
@@ -60,6 +60,7 @@
   grpc_winsocket *socket;
   grpc_tcp_server *server;
   LPFN_ACCEPTEX AcceptEx;
+  int shutting_down;
 } server_port;
 
 /* the overall server */
@@ -110,6 +111,7 @@
   /* delete ALL the things */
   for (i = 0; i < s->nports; i++) {
     server_port *sp = &s->ports[i];
+    sp->socket->closed_early = 1;
     grpc_winsocket_orphan(sp->socket);
   }
   gpr_free(s->ports);
@@ -191,8 +193,6 @@
     goto failure;
   }
 
-  /* TODO(jtattermusch): probably a race here, we regularly get use-after-free on server shutdown */
-  GPR_ASSERT(port->socket != (grpc_winsocket*)0xfeeefeee);
   success = port->AcceptEx(port->socket->socket, sock, port->addresses, 0,
                            addrlen, addrlen, &bytes_received,
                            &port->socket->read_info.overlapped);
@@ -223,6 +223,16 @@
   grpc_winsocket_callback_info *info = &sp->socket->read_info;
   grpc_endpoint *ep = NULL;
 
+  if (sp->shutting_down) {
+    sp->shutting_down = 0;
+    gpr_mu_lock(&sp->server->mu);
+    if (0 == --sp->server->active_ports) {
+      gpr_cv_broadcast(&sp->server->cv);
+    }
+    gpr_mu_unlock(&sp->server->mu);
+    return;
+  }
+
   if (success) {
     DWORD transfered_bytes = 0;
     DWORD flags;
@@ -237,12 +247,9 @@
       ep = grpc_tcp_create(grpc_winsocket_create(sock));
     }
   } else {
+    sp->shutting_down = 1;
+    sp->new_socket = INVALID_SOCKET;
     closesocket(sock);
-    gpr_mu_lock(&sp->server->mu);
-    if (0 == --sp->server->active_ports) {
-      gpr_cv_broadcast(&sp->server->cv);
-    }
-    gpr_mu_unlock(&sp->server->mu);
   }
 
   if (ep) sp->server->cb(sp->server->cb_arg, ep);
@@ -286,6 +293,7 @@
     sp = &s->ports[s->nports++];
     sp->server = s;
     sp->socket = grpc_winsocket_create(sock);
+    sp->shutting_down = 0;
     sp->AcceptEx = AcceptEx;
     GPR_ASSERT(sp->socket);
     gpr_mu_unlock(&s->mu);
diff --git a/src/core/iomgr/tcp_windows.c b/src/core/iomgr/tcp_windows.c
index 940cd5b..d5b06e7 100644
--- a/src/core/iomgr/tcp_windows.c
+++ b/src/core/iomgr/tcp_windows.c
@@ -130,6 +130,7 @@
     gpr_log(GPR_ERROR, "ReadFile overlapped error: %s", utf8_message);
     gpr_free(utf8_message);
     status = GRPC_ENDPOINT_CB_ERROR;
+    socket->closed_early = 1;
   } else {
     if (info->bytes_transfered != 0) {
       sub = gpr_slice_sub(tcp->read_slice, 0, info->bytes_transfered);
@@ -225,6 +226,7 @@
     gpr_log(GPR_ERROR, "WSASend overlapped error: %s", utf8_message);
     gpr_free(utf8_message);
     status = GRPC_ENDPOINT_CB_ERROR;
+    tcp->socket->closed_early = 1;
   } else {
     GPR_ASSERT(info->bytes_transfered == tcp->write_slices.length);
   }