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I'm working with SmarterMail 5.0 and having problems sending email from Outlook to external email accounts through my SmarterMail server. I'm just getting started with the product and only have one domain setup. I've seen quite a number of posts for this issue on the forum and have tried to follow the remedies without success.

1. I have Outlook setup to expect authetication is required for SMTP. I'm using the same account information for SMTP authorization as for POP retrevial.

2. My domain is setup with "Require SMTP Authetication" turned on under the Manage, Domain, Technical tab.

3. My mail server is setup with Allow Relay is set to "Nobody" and "Disable relay settings when using SMTP authentication" is checked on the Protocol Settings's SMTP IN tab.

 When I review the SMTP related log file after an unsuccessful send attempt I see the 550 error message.

 If I turn off the Require SMTP Authetication and set the Allow Relay setting to "Only Local Users" I can send out emails from Outlook just fine.

I've tried this both from Vista and XP. I've tried using Windows Mail, Outlook 2007 and Outlook Express. 

I'm running the email server on Windows Server 2003 R2 SP2 under IIS 6.

Any help would be appreciated.

Here is a Knowledge base article on how Outlook should be configured https://www.smartertools.com/portal/KB/a28/how-to-setting-up-pop-in-outlook.aspx?KBSearchID=8235  The last step are very important in configuring Outlook to send mail as an authenticated user.

Also, log in as the sysadmin go to Settings, Protocol Settings, SMTP IN and check Disable relay settings when using SMTP authentication then click Save.

Hope this helps.

Yes as I mentioned above, my Outlook is setup to send mail as an authenticated user. I tell Outlook to use the same username and password that works to retreive email through POP. It seems like the Auth info isn't getting to the mail server. As I mentioned I've tried the on a number of different email client besides Outlook. I've fiddled with every setting in Outlook related to specifying that SMTP has to be authorized and setting the username and password. Also, I have, the disable relay setting when using SMTP authentication checked as well.

 --Mark