diff --git a/src/core/iomgr/iocp_windows.c b/src/core/iomgr/iocp_windows.c
index 8b019e80496..aec626509aa 100644
--- a/src/core/iomgr/iocp_windows.c
+++ b/src/core/iomgr/iocp_windows.c
@@ -52,10 +52,11 @@ static OVERLAPPED g_iocp_custom_overlap;
 
 static gpr_event g_shutdown_iocp;
 static gpr_event g_iocp_done;
+static gpr_atm g_orphans = 0;
 
 static HANDLE g_iocp;
 
-static int do_iocp_work() {
+static void do_iocp_work() {
   BOOL success;
   DWORD bytes = 0;
   DWORD flags = 0;
@@ -71,14 +72,14 @@ static int do_iocp_work() {
                                       gpr_time_to_millis(wait_time));
   if (!success && !overlapped) {
     /* The deadline got attained. */
-    return 0;
+    return;
   }
   GPR_ASSERT(completion_key && overlapped);
   if (overlapped == &g_iocp_custom_overlap) {
     if (completion_key == (ULONG_PTR) &g_iocp_kick_token) {
       /* We were awoken from a kick. */
       gpr_log(GPR_DEBUG, "do_iocp_work - got a kick");
-      return 1;
+      return;
     }
     gpr_log(GPR_ERROR, "Unknown custom completion key.");
     abort();
@@ -97,8 +98,13 @@ static int do_iocp_work() {
   }
   success = WSAGetOverlappedResult(socket->socket, &info->overlapped, &bytes,
                                    FALSE, &flags);
-  gpr_log(GPR_DEBUG, "bytes: %u, flags: %u - op %s", bytes, flags,
-          success ? "succeeded" : "failed");
+  gpr_log(GPR_DEBUG, "bytes: %u, flags: %u - op %s %s", bytes, flags,
+          success ? "succeeded" : "failed", socket->orphan ? "orphan" : "");
+  if (socket->orphan) {
+    grpc_winsocket_destroy(socket);
+    gpr_atm_full_fetch_add(&g_orphans, -1);
+    return;
+  }
   info->bytes_transfered = bytes;
   info->wsa_error = success ? 0 : WSAGetLastError();
   GPR_ASSERT(overlapped == &info->overlapped);
@@ -113,12 +119,10 @@ static int do_iocp_work() {
   }
   gpr_mu_unlock(&socket->state_mu);
   if (f) f(opaque, 1);
-
-  return 1;
 }
 
 static void iocp_loop(void *p) {
-  while (!gpr_event_get(&g_shutdown_iocp)) {
+  while (gpr_atm_acq_load(&g_orphans) || !gpr_event_get(&g_shutdown_iocp)) {
     grpc_maybe_call_delayed_callbacks(NULL, 1);
     do_iocp_work();
   }
@@ -138,13 +142,19 @@ void grpc_iocp_init(void) {
   gpr_thd_new(&id, iocp_loop, NULL, NULL);
 }
 
-void grpc_iocp_shutdown(void) {
+void grpc_iocp_kick(void) {
   BOOL success;
-  gpr_event_set(&g_shutdown_iocp, (void *)1);
+
   success = PostQueuedCompletionStatus(g_iocp, 0,
                                        (ULONG_PTR) &g_iocp_kick_token,
                                        &g_iocp_custom_overlap);
   GPR_ASSERT(success);
+}
+
+void grpc_iocp_shutdown(void) {
+  BOOL success;
+  gpr_event_set(&g_shutdown_iocp, (void *)1);
+  grpc_iocp_kick();
   gpr_event_wait(&g_iocp_done, gpr_inf_future);
   success = CloseHandle(g_iocp);
   GPR_ASSERT(success);
@@ -166,6 +176,10 @@ void grpc_iocp_add_socket(grpc_winsocket *socket) {
   GPR_ASSERT(ret == g_iocp);
 }
 
+void grpc_iocp_socket_orphan(grpc_winsocket *socket) {
+  gpr_atm_full_fetch_add(&g_orphans, 1);
+}
+
 static void socket_notify_on_iocp(grpc_winsocket *socket,
                                   void(*cb)(void *, int), void *opaque,
                                   grpc_winsocket_callback_info *info) {
diff --git a/src/core/iomgr/iocp_windows.h b/src/core/iomgr/iocp_windows.h
index 33133193a10..fa3f5eee10e 100644
--- a/src/core/iomgr/iocp_windows.h
+++ b/src/core/iomgr/iocp_windows.h
@@ -42,6 +42,7 @@
 void grpc_iocp_init(void);
 void grpc_iocp_shutdown(void);
 void grpc_iocp_add_socket(grpc_winsocket *);
+void grpc_iocp_socket_orphan(grpc_winsocket *);
 
 void grpc_socket_notify_on_write(grpc_winsocket *, void(*cb)(void *, int success),
                                  void *opaque);
diff --git a/src/core/iomgr/iomgr.c b/src/core/iomgr/iomgr.c
index 058685b295d..d0e6706fbd7 100644
--- a/src/core/iomgr/iomgr.c
+++ b/src/core/iomgr/iomgr.c
@@ -117,7 +117,16 @@ void grpc_iomgr_shutdown(void) {
       gpr_mu_lock(&g_mu);
     }
     if (g_refs) {
-      if (gpr_cv_wait(&g_rcv, &g_mu, shutdown_deadline) && g_cbs_head == NULL) {
+      int timeout = 0;
+      gpr_timespec short_deadline = gpr_time_add(gpr_now(),
+                                                 gpr_time_from_millis(100));
+      while (gpr_cv_wait(&g_rcv, &g_mu, short_deadline) && g_cbs_head == NULL) {
+        if (gpr_time_cmp(gpr_now(), shutdown_deadline) > 0) {
+          timeout = 1;
+          break;
+        }
+      }
+      if (timeout) {
         gpr_log(GPR_DEBUG,
                 "Failed to free %d iomgr objects before shutdown deadline: "
                 "memory leaks are likely",
diff --git a/src/core/iomgr/socket_windows.c b/src/core/iomgr/socket_windows.c
index 99f38b0e032..22dad41783f 100644
--- a/src/core/iomgr/socket_windows.c
+++ b/src/core/iomgr/socket_windows.c
@@ -55,7 +55,7 @@ grpc_winsocket *grpc_winsocket_create(SOCKET socket) {
   return r;
 }
 
-void shutdown_op(grpc_winsocket_callback_info *info) {
+static void shutdown_op(grpc_winsocket_callback_info *info) {
   if (!info->cb) return;
   grpc_iomgr_add_delayed_callback(info->cb, info->opaque, 0);
 }
@@ -68,8 +68,13 @@ void grpc_winsocket_shutdown(grpc_winsocket *socket) {
 
 void grpc_winsocket_orphan(grpc_winsocket *socket) {
   gpr_log(GPR_DEBUG, "grpc_winsocket_orphan");
+  grpc_iocp_socket_orphan(socket);
+  socket->orphan = 1;
   grpc_iomgr_unref();
   closesocket(socket->socket);
+}
+
+void grpc_winsocket_destroy(grpc_winsocket *socket) {
   gpr_mu_destroy(&socket->state_mu);
   gpr_free(socket);
 }
diff --git a/src/core/iomgr/socket_windows.h b/src/core/iomgr/socket_windows.h
index d4776ab10f8..cbae91692cb 100644
--- a/src/core/iomgr/socket_windows.h
+++ b/src/core/iomgr/socket_windows.h
@@ -57,12 +57,13 @@ typedef struct grpc_winsocket_callback_info {
 typedef struct grpc_winsocket {
   SOCKET socket;
 
-  int added_to_iocp;
-
   grpc_winsocket_callback_info write_info;
   grpc_winsocket_callback_info read_info;
 
   gpr_mu state_mu;
+
+  int added_to_iocp;
+  int orphan;
 } grpc_winsocket;
 
 /* Create a wrapped windows handle.
@@ -71,5 +72,6 @@ grpc_winsocket *grpc_winsocket_create(SOCKET socket);
 
 void grpc_winsocket_shutdown(grpc_winsocket *socket);
 void grpc_winsocket_orphan(grpc_winsocket *socket);
+void grpc_winsocket_destroy(grpc_winsocket *socket);
 
 #endif  /* GRPC_INTERNAL_CORE_IOMGR_SOCKET_WINDOWS_H */