diff --git a/src/core/iomgr/iocp_windows.c b/src/core/iomgr/iocp_windows.c
index 807729708ea..fa87e5246b0 100644
--- a/src/core/iomgr/iocp_windows.c
+++ b/src/core/iomgr/iocp_windows.c
@@ -71,7 +71,8 @@ static DWORD deadline_to_millis_timeout(gpr_timespec deadline,
       timeout, gpr_time_from_nanos(GPR_NS_PER_MS - 1, GPR_TIMESPAN)));
 }
 
-void grpc_iocp_work(grpc_exec_ctx *exec_ctx, gpr_timespec deadline) {
+grpc_iocp_work_status grpc_iocp_work(grpc_exec_ctx *exec_ctx,
+                                     gpr_timespec deadline) {
   BOOL success;
   DWORD bytes = 0;
   DWORD flags = 0;
@@ -84,14 +85,14 @@ void grpc_iocp_work(grpc_exec_ctx *exec_ctx, gpr_timespec deadline) {
       g_iocp, &bytes, &completion_key, &overlapped,
       deadline_to_millis_timeout(deadline, gpr_now(deadline.clock_type)));
   if (success == 0 && overlapped == NULL) {
-    return;
+    return GRPC_IOCP_WORK_TIMEOUT;
   }
   GPR_ASSERT(completion_key && overlapped);
   if (overlapped == &g_iocp_custom_overlap) {
     gpr_atm_full_fetch_add(&g_custom_events, -1);
     if (completion_key == (ULONG_PTR)&g_iocp_kick_token) {
       /* We were awoken from a kick. */
-      return;
+      return GRPC_IOCP_WORK_KICK;
     }
     gpr_log(GPR_ERROR, "Unknown custom completion key.");
     abort();
@@ -121,6 +122,7 @@ void grpc_iocp_work(grpc_exec_ctx *exec_ctx, gpr_timespec deadline) {
   }
   gpr_mu_unlock(&socket->state_mu);
   grpc_exec_ctx_enqueue(exec_ctx, closure, true, NULL);
+  return GRPC_IOCP_WORK_WORK;
 }
 
 void grpc_iocp_init(void) {
@@ -140,10 +142,12 @@ void grpc_iocp_kick(void) {
 
 void grpc_iocp_flush(void) {
   grpc_exec_ctx exec_ctx = GRPC_EXEC_CTX_INIT;
+  grpc_iocp_work_status work_status;
 
   do {
-    grpc_iocp_work(&exec_ctx, gpr_inf_past(GPR_CLOCK_MONOTONIC));
-  } while (grpc_exec_ctx_flush(&exec_ctx));
+    work_status = grpc_iocp_work(&exec_ctx, gpr_inf_past(GPR_CLOCK_MONOTONIC));
+  } while (work_status == GRPC_IOCP_WORK_KICK ||
+           grpc_exec_ctx_flush(&exec_ctx));
 }
 
 void grpc_iocp_shutdown(void) {
diff --git a/src/core/iomgr/iocp_windows.h b/src/core/iomgr/iocp_windows.h
index 75f3ba84770..8b2b1aeb5c2 100644
--- a/src/core/iomgr/iocp_windows.h
+++ b/src/core/iomgr/iocp_windows.h
@@ -1,6 +1,6 @@
 /*
  *
- * Copyright 2015, Google Inc.
+ * Copyright 2015-2016, Google Inc.
  * All rights reserved.
  *
  * Redistribution and use in source and binary forms, with or without
@@ -38,7 +38,14 @@
 
 #include "src/core/iomgr/socket_windows.h"
 
-void grpc_iocp_work(grpc_exec_ctx *exec_ctx, gpr_timespec deadline);
+typedef enum {
+  GRPC_IOCP_WORK_WORK,
+  GRPC_IOCP_WORK_TIMEOUT,
+  GRPC_IOCP_WORK_KICK
+} grpc_iocp_work_status;
+
+grpc_iocp_work_status grpc_iocp_work(grpc_exec_ctx *exec_ctx,
+                                     gpr_timespec deadline);
 void grpc_iocp_init(void);
 void grpc_iocp_kick(void);
 void grpc_iocp_flush(void);
diff --git a/src/core/iomgr/tcp_server_windows.c b/src/core/iomgr/tcp_server_windows.c
index ce930b8f41d..a4abc5b9743 100644
--- a/src/core/iomgr/tcp_server_windows.c
+++ b/src/core/iomgr/tcp_server_windows.c
@@ -240,8 +240,7 @@ static void decrement_active_ports_and_notify(grpc_exec_ctx *exec_ctx,
   sp->shutting_down = 0;
   gpr_mu_lock(&sp->server->mu);
   GPR_ASSERT(sp->server->active_ports > 0);
-  if (0 == --sp->server->active_ports &&
-      sp->server->shutdown_complete != NULL) {
+  if (0 == --sp->server->active_ports) {
     notify = 1;
   }
   gpr_mu_unlock(&sp->server->mu);