Unable to Send Email Notification for Alerts

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You setup email notification for alerts and configure the setting for "This server requires a secure connection (SSL)" but the email notifications fail to be sent.


One of the possible causes could be the type of secure connection the SMTP mail server requires. The SSL configuration of Email notficiation of alerts uses the .Net Framework 4 SmtpClient.EnableSsl Property as defined at http://msdn.microsoft.com/en-us/library/system.net.mail.smtpclient.enablessl.aspxsupport . The EnableSsl property supports the SMTP Service Extension for Secure SMTP over Transport Layer Security (TLS) as defined in RFC 3207. In this mode, the SMTP session begins on an unencrypted channel, then a STARTTLS command is issued by the client to the server to switch to secure communication using SSL. See RFC 3207 published by the Internet Engineering Task Force (IETF) for more information. An alternate connection method is where an SSL session is established up front before any protocol commands are sent. This connection method is sometimes called SMTP/SSL, SMTP over SSL, or SMTPS and by default uses port 465. This alternate connection method using SSL is not currently supported. 


You must work with the mail server administrator to determine the proper settings for the email notifications.


You can determine if the email server supports SMTP over TLS by using the telnet client. The telnet client is not installed by default on the Server. You can install it by using Server Manager and going to features and choosing to add the telnet client or you can perform the test from a client machine. From a command prompt you would enter:

Telnet<mailservername><port number>where mailservername and portnumber are the name of the mail server and the port number. For example, telnet smtp.live.com 587

You will see a connection header similar to the following:

220 BLU0-SMTP39.blu0.hotmail.com Microsoft ESMTP MAIL Service, Version: 6.0.3790.4675 ready at  Mon, 7 Mar 2011 11:35:40 -0800


The mail server will return the SMTP commands it supports. For example you will see a list similar to this:

250-BLU0-SMTP39.blu0.hotmail.com Hello
250-SIZE 41943040
250 OK

If the command STARTTLS is in the list, then the mail server supports SMTP over TLS and we can check the box for the server requires a secure connection (SSL).

Note This is a "FAST PUBLISH" article created directly from within the Microsoft support organization. The information contained herein is provided as-is in response to emerging issues. As a result of the speed in making it available, the materials may include typographical errors and may be revised at any time without notice. See Terms of Use for other considerations.


Article ID: 2519903 - Last Review: March 28, 2011 - Revision: 3.0
  • Windows Home Server 2011
  • Windows Storage Server 2008 R2 Essentials
  • Windows Small Business Server 2011 Essentials

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