I think I am facing the same problem here, but the messages are different. My configurations are:
- From Email: site@mydomain.com
- From Name: My Site
- [Checked] Send all WordPress emails via SMTP.
- [Checked] Set the return-path to match the From Email
- SMTP Host: smtp.gmail.com
- SMTP Port: 587
- Encryption: Use TLS encryption.
- Authentication: Yes: Use SMTP authentication.
- Username: site@mydomain.com
- Password: <myPassword>
The SMTP debugging output is shown below:
SMTP -> ERROR: Failed to connect to server: Connection timed out (110)My Wordpress Version: 4.0.1
Plugin Version: 0.9.5
PHP Version: 5.4