sometimes sharepoint email alerts are not properly working, and its very difficult to find actual error cause.
I also faced lots of problem with same issue, on development server alerts works like charm but on installable server, email alerts not working..
I searched for solution but didn't get anything, all outgoing email configuration in Central Admin correct.
So i checked email error from following utility, you can download from
http://www.codeplex.com/rodneyviana/Release/ProjectReleases.aspx?ReleaseId=19103
you can extract only the .exe file (SendMail\bin\Debug\SendMail.exe) and run it without any installation. This application will send an e-mail. Enter the url of a valid sharepoint site and a valid user login name for that site which will be the recipient of the test email message. The application will display the e-mail information from the sharepoint site user login name.
for more information please have a look at
http://blogs.msdn.com/rodneyviana/archive/2008/11/06/how-to-test-the-mail-settings-for-a-sharepoint-web-application.aspx
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