diff --git a/src/tls_wrap.cc b/src/tls_wrap.cc
index 803bc4edcf7..c01b320343d 100644
--- a/src/tls_wrap.cc
+++ b/src/tls_wrap.cc
@@ -473,6 +473,11 @@ void TLSCallbacks::ClearOut() {
     Local<Value> arg = GetSSLError(read, &err, NULL);
 
     if (!arg.IsEmpty()) {
+      // When TLS Alert are stored in wbio,
+      // it should be flushed to socket before destroyed.
+      if (BIO_pending(enc_out_) != 0)
+        EncOut();
+
       MakeCallback(env()->onerror_string(), 1, &arg);
     }
   }
diff --git a/test/simple/test-tls-alert.js b/test/simple/test-tls-alert.js
new file mode 100644
index 00000000000..f26b496f9df
--- /dev/null
+++ b/test/simple/test-tls-alert.js
@@ -0,0 +1,63 @@
+// Copyright Joyent, Inc. and other Node contributors.
+//
+// Permission is hereby granted, free of charge, to any person obtaining a
+// copy of this software and associated documentation files (the
+// "Software"), to deal in the Software without restriction, including
+// without limitation the rights to use, copy, modify, merge, publish,
+// distribute, sublicense, and/or sell copies of the Software, and to permit
+// persons to whom the Software is furnished to do so, subject to the
+// following conditions:
+//
+// The above copyright notice and this permission notice shall be included
+// in all copies or substantial portions of the Software.
+//
+// THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS
+// OR IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF
+// MERCHANTABILITY, FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN
+// NO EVENT SHALL THE AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM,
+// DAMAGES OR OTHER LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR
+// OTHERWISE, ARISING FROM, OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE
+// USE OR OTHER DEALINGS IN THE SOFTWARE.
+
+var common = require('../common');
+
+if (!common.opensslCli) {
+  console.error('Skipping because node compiled without OpenSSL CLI.');
+  process.exit(0);
+}
+
+var assert = require('assert');
+var fs = require('fs');
+var tls = require('tls');
+var spawn = require('child_process').spawn;
+
+var success = false;
+
+function filenamePEM(n) {
+  return require('path').join(common.fixturesDir, 'keys', n + '.pem');
+}
+
+function loadPEM(n) {
+  return fs.readFileSync(filenamePEM(n));
+}
+
+var server = tls.Server({
+  secureProtocol: 'TLSv1_2_server_method',
+  key: loadPEM('agent2-key'),
+  cert:loadPEM('agent2-cert')
+}, null).listen(common.PORT, function() {
+  var args = ['s_client', '-quiet', '-tls1_1','-connect', '127.0.0.1:' + common.PORT];
+  var client = spawn(common.opensslCli, args);
+  var out = '';
+  client.stderr.setEncoding('utf8');
+  client.stderr.on('data', function(d) {
+    out += d;
+    if (/SSL alert number 70/.test(out)) {
+      success = true;
+      server.close();
+    }
+  });
+});
+process.on('exit', function() {
+  assert(success);
+});