Its not cloudstack related error. There is some problem with your smtp server. 
See if this link can help you 
http://www.carehart.org/blog/client/index.cfm/2009/4/18/cfmail_530_error. Try 
googling with the same error.

From: zcsu [mailto:szc...@hotmail.com]
Sent: Thursday, March 27, 2014 12:22 PM
To: dev@cloudstack.apache.org; Anshul Gangwar
Subject: RE: Alert Email must be SSL?

Thanks anshul

The others global setting is the same

if alert.smtp.useAuth   is default value,
Error Log is:

2014-03-27 14:48:29,819 ERROR [cloud.alert.AlertManagerImpl] 
(Email-Alerts-Sender-1:null)  Failed to send email alert 
com.sun.mail.smtp.SMTPSendFailedException: 530 5.7.3 Client was not 
authenticated

if alert.smtp.useAuth is true

 2014-03-27 13:31:45,687 ERROR [cloud.alert.AlertManagerImpl] 
(Email-Alerts-Sender-1:null) Failed to send email alert 
javax.mail.MessagingException: Exception reading response 
(javax.net.ssl.SSLException: Unrecognized SSL message, plaintext connection?)


> From: anshul.gang...@citrix.com
> To: dev@cloudstack.apache.org
> Subject: RE: Alert Email must be SSL?
> Date: Thu, 27 Mar 2014 06:38:25 +0000
>
> Have you configured your smtp host and port correctly?
>
> If there is authentication enabled then you have set the appropriate global 
> setting alert.smtp.useAuth etc.
>
> Regards,
> Anshul
>
> -----Original Message-----
> From: zcsu [mailto:szc...@hotmail.com]<mailto:[mailto:szc...@hotmail.com]>
> Sent: Thursday, March 27, 2014 11:20 AM
> To: dev@cloudstack.apache.org<mailto:dev@cloudstack.apache.org>
> Subject: Alert Email must be SSL?
>
> Hi
>
> I configured Alert Email in Global Setting, but i don't receive any alert, I 
> find ERROR info in management-server.log as below,
>
> 2014-03-27 13:31:45,687 ERROR [cloud.alert.AlertManagerImpl] 
> (Email-Alerts-Sender-1:null) Failed to send email alert 
> javax.mail.MessagingException: Exception reading response 
> (javax.net.ssl.SSLException: Unrecognized SSL message, plaintext connection?)
>
>
> CloudStack 4.2 +CentOS 6.4
>
> [Question] How to correctly Alert Email? Anybody answer me, thank a million.
>
>

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