Hi! I'm running an app on ubuntu 12 that is based on CakePHP. I was just migrating the app and everything is working, but i have errors every time I try to send e-mails with my gmail account. This app is totally tested and work 100% but here in DigitalOcean the SMTP connection seems to be impossible.... any idea? My basic config (and i know 100% it's OK because the app is already working on at least 4 servers) is: public $mail = array( 'transport' => 'Smtp', 'host' => 'ssl://smtp.gmail.com', 'from' => array('user@web.com' => 'Pretty Name here'), 'port' => 465, 'timeout' => 30, 'username' => 'myname@mymail.com', 'password' => 'mypass', 'emailFormat' => 'html' ); using CakePHP and CakeEmail function. As I said, everything works perfectly on other servers. And no, it's not a gmail ban, because I tried to install the app on another server after installing it here and everything is still working... Any idea about why is SMTP blocked?? My cake say: Connection timed out and the trace: CORE/Cake/Network/Email/SmtpTransport.php line 99 CakeSocket->connect() protected function _connect(){ $this->_generateSocket() } I've tried lot of thing, but nothing seems to work.. any ideas? it's a little big urgency ^ ^