diff --git a/src/win/error.c b/src/win/error.c
index 3f6615f5..5d695696 100644
--- a/src/win/error.c
+++ b/src/win/error.c
@@ -91,6 +91,8 @@ uv_err_code uv_translate_sys_error(int sys_errno) {
     case WSAEFAULT:                         return UV_EFAULT;
     case ERROR_HOST_UNREACHABLE:            return UV_EHOSTUNREACH;
     case WSAEHOSTUNREACH:                   return UV_EHOSTUNREACH;
+    case ERROR_OPERATION_ABORTED:           return UV_EINTR;
+    case WSAEINTR:                          return UV_EINTR;
     case ERROR_INVALID_DATA:                return UV_EINVAL;
     case WSAEINVAL:                         return UV_EINVAL;
     case ERROR_CANT_RESOLVE_FILENAME:       return UV_ELOOP;
diff --git a/src/win/handle.c b/src/win/handle.c
index a4eadbdd..a1ff7275 100644
--- a/src/win/handle.c
+++ b/src/win/handle.c
@@ -91,9 +91,10 @@ void uv_close(uv_handle_t* handle, uv_close_cb cb) {
       tcp = (uv_tcp_t*)handle;
       /* If we don't shutdown before calling closesocket, windows will */
       /* silently discard the kernel send buffer and reset the connection. */
-      if (!(tcp->flags & UV_HANDLE_SHUT)) {
+      if ((tcp->flags & UV_HANDLE_CONNECTION) &&
+          !(tcp->flags & UV_HANDLE_SHUT)) {
         shutdown(tcp->socket, SD_SEND);
-        tcp->flags |= UV_HANDLE_SHUT;
+        tcp->flags |= UV_HANDLE_SHUTTING | UV_HANDLE_SHUT;
       }
       tcp->flags &= ~(UV_HANDLE_READING | UV_HANDLE_LISTENING);
       closesocket(tcp->socket);
diff --git a/src/win/pipe.c b/src/win/pipe.c
index ab86018d..f99a32a9 100644
--- a/src/win/pipe.c
+++ b/src/win/pipe.c
@@ -281,11 +281,25 @@ void uv_pipe_endgame(uv_loop_t* loop, uv_pipe_t* handle) {
   IO_STATUS_BLOCK io_status;
   FILE_PIPE_LOCAL_INFORMATION pipe_info;
 
-  if (handle->flags & UV_HANDLE_SHUTTING &&
-      !(handle->flags & UV_HANDLE_SHUT) &&
+  if ((handle->flags & UV_HANDLE_CONNECTION) &&
+      handle->shutdown_req != NULL &&
       handle->write_reqs_pending == 0) {
     req = handle->shutdown_req;
 
+    /* Clear the shutdown_req field so we don't go here again. */
+    handle->shutdown_req = NULL;
+
+    if (handle->flags & UV_HANDLE_CLOSING) {
+      /* Already closing. Cancel the shutdown. */
+      if (req->cb) {
+        uv__set_sys_error(loop, WSAEINTR);
+        req->cb(req, -1);
+      }
+      uv_unref(loop);
+      DECREASE_PENDING_REQ_COUNT(handle);
+      return;
+    }
+
     /* Try to avoid flushing the pipe buffer in the thread pool. */
     nt_status = pNtQueryInformationFile(handle->handle,
                                         &io_status,
@@ -306,8 +320,6 @@ void uv_pipe_endgame(uv_loop_t* loop, uv_pipe_t* handle) {
     }
 
     if (pipe_info.OutboundQuota == pipe_info.WriteQuotaAvailable) {
-      handle->flags |= UV_HANDLE_SHUT;
-
       /* Short-circuit, no need to call FlushFileBuffers. */
       uv_insert_pending_req(loop, (uv_req_t*) req);
       return;
@@ -318,8 +330,6 @@ void uv_pipe_endgame(uv_loop_t* loop, uv_pipe_t* handle) {
                                req,
                                WT_EXECUTELONGFUNCTION);
     if (result) {
-      /* Mark the handle as shut now to avoid going through this again. */
-      handle->flags |= UV_HANDLE_SHUT;
       return;
 
     } else {
@@ -625,6 +635,7 @@ void close_pipe(uv_pipe_t* handle, int* status, uv_err_t* err) {
   }
 
   if (handle->flags & UV_HANDLE_CONNECTION) {
+    handle->flags |= UV_HANDLE_SHUTTING;
     eof_timer_destroy(handle);
   }
 
@@ -633,8 +644,6 @@ void close_pipe(uv_pipe_t* handle, int* status, uv_err_t* err) {
     CloseHandle(handle->handle);
     handle->handle = INVALID_HANDLE_VALUE;
   }
-
-  handle->flags |= UV_HANDLE_SHUT;
 }
 
 
diff --git a/src/win/stream.c b/src/win/stream.c
index 53c4d9ec..d36bc682 100644
--- a/src/win/stream.c
+++ b/src/win/stream.c
@@ -47,6 +47,8 @@ void uv_connection_init(uv_stream_t* handle) {
   handle->read_req.wait_handle = INVALID_HANDLE_VALUE;
   handle->read_req.type = UV_READ;
   handle->read_req.data = handle;
+
+  handle->shutdown_req = NULL;
 }
 
 
diff --git a/src/win/tcp.c b/src/win/tcp.c
index 31de8448..25ca26bd 100644
--- a/src/win/tcp.c
+++ b/src/win/tcp.c
@@ -171,11 +171,13 @@ void uv_tcp_endgame(uv_loop_t* loop, uv_tcp_t* handle) {
   uv_tcp_accept_t* req;
 
   if (handle->flags & UV_HANDLE_CONNECTION &&
-      handle->flags & UV_HANDLE_SHUTTING &&
-      !(handle->flags & UV_HANDLE_SHUT) &&
+      handle->shutdown_req != NULL &&
       handle->write_reqs_pending == 0) {
 
-    if (shutdown(handle->socket, SD_SEND) != SOCKET_ERROR) {
+    if (handle->flags & UV_HANDLE_CLOSING) {
+      status = -1;
+      sys_error = WSAEINTR;
+    } else if (shutdown(handle->socket, SD_SEND) != SOCKET_ERROR) {
       status = 0;
       handle->flags |= UV_HANDLE_SHUT;
     } else {
@@ -189,6 +191,8 @@ void uv_tcp_endgame(uv_loop_t* loop, uv_tcp_t* handle) {
       handle->shutdown_req->cb(handle->shutdown_req, status);
     }
 
+    handle->shutdown_req = NULL;
+
     uv_unref(loop);
     DECREASE_PENDING_REQ_COUNT(handle);
     return;
diff --git a/src/win/tty.c b/src/win/tty.c
index 2a696c89..601bf5ed 100644
--- a/src/win/tty.c
+++ b/src/win/tty.c
@@ -1721,6 +1721,8 @@ void uv_process_tty_write_req(uv_loop_t* loop, uv_tty_t* handle,
 
 
 void uv_tty_close(uv_tty_t* handle) {
+  handle->flags |= UV_HANDLE_SHUTTING;
+
   uv_tty_read_stop(handle);
   CloseHandle(handle->handle);
 
@@ -1731,17 +1733,21 @@ void uv_tty_close(uv_tty_t* handle) {
 
 
 void uv_tty_endgame(uv_loop_t* loop, uv_tty_t* handle) {
-  if (handle->flags & UV_HANDLE_CONNECTION &&
-      handle->flags & UV_HANDLE_SHUTTING &&
-      !(handle->flags & UV_HANDLE_SHUT) &&
+  if ((handle->flags && UV_HANDLE_CONNECTION) &&
+      handle->shutdown_req != NULL &&
       handle->write_reqs_pending == 0) {
-    handle->flags |= UV_HANDLE_SHUT;
-
     /* TTY shutdown is really just a no-op */
     if (handle->shutdown_req->cb) {
-      handle->shutdown_req->cb(handle->shutdown_req, 0);
+      if (handle->flags & UV_HANDLE_CLOSING) {
+        uv__set_sys_error(loop, WSAEINTR);
+        handle->shutdown_req->cb(handle->shutdown_req, -1);
+      } else {
+        handle->shutdown_req->cb(handle->shutdown_req, 0);
+      }
     }
 
+    handle->shutdown_req = NULL;
+
     uv_unref(loop);
     DECREASE_PENDING_REQ_COUNT(handle);
     return;