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Anyone using Outlook.com SMTP service and having issues?

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.

Server Error
fwrite() [function.fwrite]: SSL operation failed with code 1. OpenSSL Error messages: error:1409F07F:SSL routines:SSL3_WRITE_PENDING:bad write retry
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?


Jake Bunce

XenForo moderator
Staff member
This might help:


Screen shot 2013-01-03 at 2.22.35 PM.png

There are also reports of this being caused by a faulty OpenSSL library in PHP. Your host or server person should try patching that library. Example:


Comment 2 by fidojo...@gmail.com, Mar 23, 2010

Ok I upgrade the php to the last version from branch 5.2 and same result. So I repack
openssl package 0.9.8g for debian lenny applying the patch and now works perfect. I
don't understand why this patch itsn't applyed in official openssl package. Thanks
for the tip.