I am having a terrible time trying to troubleshoot an SMTP issue with ActiveSocial on our site. Regulard DotNetNuke notification emails - new users, role assignments, etc. - work. However, all the ActiveSocial email attempts generate exceptions. The exception below is copied from the Log Viewer after I attempted to send a private message to myself with email notifications turned on.

AssemblyVersion: 5.1.4
PortalID: 0
PortalName: Issaquah Soccer Club
UserID: 3
UserName: ray
ActiveTabID: 305
ActiveTabName: Messaging
RawURL: /Messaging/tabid/305/aspm/compose/Default.aspx
AbsoluteURL: /Default.aspx
AbsoluteURLReferrer: http://issaquahsoccerclub.org/Messa...fault.aspx
UserAgent: Mozilla/4.0 (compatible; MSIE 8.0; Windows NT 6.1; Trident/4.0; SLCC2; .NET CLR 2.0.50727; .NET CLR 3.5.30729; .NET CLR 3.0.30729; Media Center PC 6.0; Tablet PC 2.0; Zune 4.0; InfoPath.3; MS-RTC LM 8)
DefaultDataProvider: DotNetNuke.Data.SqlDataProvider, DotNetNuke.SqlDataProvider
ExceptionGUID: 64d59079-1dcb-46cc-958b-8b1acbd29d90
InnerException: The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.1 Client was not authenticated
FileName:
FileLineNumber: 0
FileColumnNumber: 0
Method: System.Net.Mail.MailCommand.CheckResponse
StackTrace:
Message: System.Net.Mail.SmtpException: The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.1 Client was not authenticated at System.Net.Mail.MailCommand.CheckResponse(SmtpStatusCode statusCode, String response) at System.Net.Mail.MailCommand.Send(SmtpConnection conn, Byte[] command, String from) at System.Net.Mail.SmtpTransport.SendMail(MailAddress sender, MailAddressCollection recipients, String deliveryNotify, SmtpFailedRecipientException& exception) at System.Net.Mail.SmtpClient.Send(MailMessage message) at Active.Modules.Social.Email.SendNotification(String FromEmail, String ToEmail, String Subject, String BodyText, String BodyHTML)
Source:
Server Name: CLE02WEB06

The exception shown above is typical of all the attempts to send notification emails from ActiveSocial. I have tried setting and emptying the email address field in the ActiveSocial settings.

This is running on DotNetNuke 5.1.4 and, as I mentioned, all the regular SMTP is working, including test messages from Host Settings. It's as if ActiveSocial isn't attempting to log in to the SMTP server or it is attempting to log in using different credentials than those specified in the Host Settings.

Has anyone else experienced something like this? Can anyone suggest a way to troubleshoot this?

Thanks,
Ray

I know there have been issues with sending messages to yourself. Really not a good way to test. Can you try sending to another account?

I have sent several messages to other accounts, including regular messages and friend requests, and all of the attempts generate exceptions displayed by Event Viewer that are similar to the one I posted.

ActiveSocial isn't attempting to send the SMTP message as the DNN user is it?

The error above isn't that authentication is failing, it's that "secure" authentication is failing. I can't remember right now, but does 5.1.4 include an option to enable secure smtp? If so, do you have it enabled?

Yes, 5.1.4 has the secure SMTP setting and it's enabled. Itls required for our SMTP server.

Is Active Forums sending email fine? What kind of Authentication are you using?

I just checked and forum notifications are not working, either. We are using Basic authentication with secure connections enabled for our SMTP settings.

My last post hasn't been approved yet and I wrote too soon.Forum notification emails are working. I didn't get notification messages for posts needing moderation, but I did get emails after I approved them.