I used to use Google Apps for all of my domains, but they don't offer the free service any more, so I switched to outlook for my newest forum project. I'm trying to send mail by connecting to smtp.live.com, tls, 587 and I'm getting the errors below. This config was working before, but recently stopped. I tried ssl/465 also and it gives me the same errors. When I send a "test" email to myself, it says it sends, but I don't get anything in my inbox. Also, I am sending mail through this account just fine via gmail with an smtp connection to this live.com account, so it doesn't sound like live.com is the problem. I've seen this error talked about a bunch of this board and tried the suggested solutions, but none seem to work. Anyone else have this issue and get it resolved? I'm hosting with Namecheap on a VPS. Code: Server Error fwrite() [function.fwrite]: SSL operation failed with code 1. OpenSSL Error messages: error:1409F07F:SSL routines:SSL3_WRITE_PENDING:bad write retry XenForo_Application::handlePhpError() fwrite() in Zend/Mail/Protocol/Abstract.php at line 324 Zend_Mail_Protocol_Abstract->_send() in Zend/Mail/Protocol/Smtp.php at line 385 Zend_Mail_Protocol_Smtp->quit() in Zend/Mail/Transport/Smtp.php at line 144 Zend_Mail_Transport_Smtp->__destruct() in XenForo/FrontController.php at line 310 XenForo_ControllerAdmin_User->actionEmailSend() in XenForo/FrontController.php at line 310 XenForo_FrontController->dispatch() in XenForo/FrontController.php at line 132 XenForo_FrontController->run() in /home/xyz/public_html/forum/admin.php at line 13 Does this sound like a server issue, or does it have to do with Xenforo? Thanks!