I have spent the last couple hours trying to get my DNN portal setup with Google Apps, but with no luck.  I have tried all the combinations I could think of (Authentication: basic, NTLM) Req SSL but the error below keeps happening.

I can connect to my Google apps account via Outlook and SMTP works.  I tried to telnet to gmail:587 and that works, but I keep getting the error:

System.Net.Mail.SmtpException: The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.5.1 Authentication Required n5sm2316268rnf 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 DotNetNuke.Services.Mail.Mail.SendMail(String MailFrom, String MailTo, String Cc, String Bcc, MailPriority Priority, String Subject, MailFormat BodyFormat, Encoding BodyEncoding, String Body, String[] Attachment, String SMTPServer, String SMTPAuthentication, String SMTPUsername, String SMTPPassword, Boolean SMTPEnableSSL)

Yes, you are correct and it is ridiculous in a multi-portal system to have to use the same server for all portals. This is the primary cause of bounced emails when it doesn't resolve backawards. I have some portal owners set up with Google Apps and others with my main host, but their portal notifications all have to go through a generic smtp designed for forms and scripts and it regularly loses emails.

The issue is a fundamental one that affects several other options as well and has been brought up many times for years now. My most recent attempt was rejected just a week or two ago: http://support.dotnetnuke.com/issue/ViewIssue.aspx?id=6805&PROJID=23

Perhaps make another post in Gemini.. if you bring it up as a single issue about the smtp server rather than as the broader issue I did, then it might be easier for the gatekeeper to understand and pass on appropriately?

It'd certainly be better than wating another years.

Rob