Code Crafters

If I connect to the SMTP server with authentication on. (It is fine without any authentication.) If I turn it on I get the following problems.

Outlook:
If I select "use same setting as my incoming mail server" or "Log on using" with or without requrie SPA, I get the following message: "None of the authentication methods supported by this client are supported by your server".

If I choose 'Log on to the incoming mail server before sending mail" (which I have activated on the server), it works fine.

Iphone: I get "'mail.insureyoutoo.com' doesn't support Password authentication. Please check your account settings and try again."

Any thoughts on what is going on?

You need to enable SMTP authentication in your mail server or you're an open relay and SPAM can be relayed via your mail server causing your IP to be blocked pretty quickly!

In your mail client do not tick SPA or SASL authentication. Just enter your username / password in your incoming mail server then in the outgoing mail server enter the same information (as long as you set AMS to allow any user account credentials with SMTP auth). In outlook, press the More Settings button then on the Outgoing Server tab tick to use the same credentials as for the incoming mail server.

Once set up, try relaying to an external email address and this should work fine. If it doesn't check the SMTP logs on AMS and tell me the error and I'll explain what this probably means.

I'm not sure you read my email correctly. Yes, I need SMTP auth, that's why this is a problem

I don't have any SPA, SASL, SSl or any other encription/auth checked. (otherwise pop before send wouldn't work either)

Yes, I know about the more settings. and I described that I did use same credentials as incoming mail server, which didn't work. That's the whole point of this post.

I've attached screenshots and logs to this post. The logs include.... ( OK,this systems is limited so I only got some of them. Will send more on request)

1) the log of the error when I use same credentials as incoming server.
2) PDF of my email setup, the server setup, and the error messages so you can see I'm not nuts.
3) A log of connecting with the iphone. The IPhone tries SSL, the non-SSL once it fails. It has no ability to do pop before incoming

Any update?

Here is a new log file for the SMTP. It has full debug turned on

The email2 attachment shows that the client wants to use some kind of authentication method (secure login) but none of the ones it supports are supported by AMS. The debug log also shows a successful EHLO SMTP authentication and POP before SMTP relaying authentication but then after showing the feature list the client then disconnects.

You must have either selected some security option other than the defaults for the outlook account or something in the SMTP settings such as Disable AUTH Reporting in the security tab.

Thanks it was the Disable AUTH. I don't know how that got checked.

No problem. Glad that solved the issue.