I have an instance setup on wildpony.net, seems to be working fine email and all. I set up a parent portal from here (jacksonnjgop.com) and I sent out email from the ADMIN-->Newsletters section. I got the email (because I'm on the same server) but anyone on an outside account didn't. Here is the error message I got.

Bulkmail Report

Operation started at: 1/30/2009 10:41:35 AM

EmailRecipients: 17

EmailMessages: 2

Operation completed: 1/30/2009 10:41:36 AM

Number of errors:15

Status Report:

Bad sequence of commands. The server response was: This mail server requires authentication when attempting to send to a non-local e-mail address. Please check your mail client settings or contact your administrator to verify that the domain or address is defined for this server.

Here is what I got from my technical support.
This error is because you are attempting to relay through the server wtihout authentication to a remote address. By default we have this disabled due to spam and security issues this can cause. Please just authenticate your sessions, so that you do not receive this error.
 and
Login as the DNN administrator

Go to Host > Host Settings

Scroll Down and Expand SMTP

Select Normal as the authentication type

Input a username and password that is local on the server



This should now allow you to send messages from that email account to remote accounts.

Is this a question, or an answer?

If it is a question, the answer is in the response you got from your tech support.

If it is an answer, thanks for the information!

Both a question and an answer, however, one that doesn't seem to work. That's why I thought I would post here for any further comments. The SMTP seems to work when I "test" but when I actually do the email, I get the error. Any suggestions? Is the SMTP setup per instance or does it change on every portal (parent or child)?

Peter

It's really NOT a DotNetNuke issue, but is an issue with the way that SMTP server is configured.

Presumably you get the test email because your address is within the domain to which the SMTP server can send.

The problem occurs when you try to send a message to an address outside of the SMTP server's comfort zone. You are going to have to work with your tech support staff to have this fixed. The SMTP server needs to recognize that mail sent through it by DotNetNuke is legitimate, and not an attempt to send spam through it.

If you did configure DotNetNuke to use an authenticated username and password, the SMTP server is not recognizing it. That's an SMTP server configuration issues.

Just as a resolution to this thread, I enabled Relaying on the mail server and that resolved the issue.

Peter

Yep.  Glad you sorted it out.

Ok one last thing for everyones edification. if you enable relaying, as previously stated, you may have spam and security issues. So the recommended practice is to set up SMTP authentication. I have modified the configuration to use the localhost and only the server IP to send from. This should help secure the relaying as well as still providing the ability to send the messages via DNN. If anyone has a different way, I'd love to hear it.

Thanks
Peter

This really is an issue of SMTP server configuration.  It's not really at DotNetNuke issue.

If you configure the SMTP server for relaying, as you noted, then anyone can use the SMTP server.  That's the spam issue.  Also, if you use an open SMTP server to send email, you stand the chance of this being discovered by the systems that look for spam.  You SMTP server could end up on a "blacklist" and many email systems will refuse to accept incoming mail from you.

Authentication requires that you use a username/password when you go to use the SMTP server.  As you noted, this is much more secure.  It's also less of a hassle regarding the blacklist issues.

Be aware, though, that if you send lots of email this way, you might still end up on a blacklist ... just for sending lots of email.  Most of the blacklist maintainers provide methods by which you can get your site on their "white lists."

Yes and thanks Joe, Is there a better way to email from DotNetNuke or is this pretty much it? I know this was a server issue , but I think it needs to be said because it's all related to setting up DNN sites and services.

Peter

Sending email is always going to rely on an SMTP server.  So, this is something that you can't avoid.

Besides the built-in Newsletter module, there are third party modules for sending emails.  If you plan to send a lot of "bulk" email, you'll have to deal with the opt-out issue and give recipients a method to unsubscribe.

There are third-party modules that do this.  Check Snowcovered or Google to find them.

You might also want to deal with a third-party email service.  Constant Contact is one.  There are others.

I believe that I also saw one module for DotNetNuke that integrates with a third-party service.

We have this post to help people understand SMTP in DNN.

We have also built custom SMTP options into our DNN email module to allow people to use services like gmail and hotmail.