Use the syntax:

 # For plain SMTP, use:
 #     $msg->send("my.name@my.domain.com"); 
 #
 #For Mime::LITE, use this syntax to create the object:

    my $msg = MIME::Lite->new(
           From     =>'my.name@myhost.com',
         ....
[download]

MIME::Lite->send('smtp','some.host',Debug=>1);
[download]

Thanks for your help, the weird part is if I switch the From -> and To -> email addresses, it sends.

Could be there is nothing weird about that. Most SMTP servers are configured to accept mail to the local domain from anywhere and to send mail only from the local domain. This prevents some unauthorised machine (eg outside your local network) from using your mail server to spam mail to the world in general.

If your "From" address is somewhere inside your network and your "To" address is outside then the mail server should refuse to accept mail to the "To" address without authentication, while it may be happy to accept any message to the "From" address since that is a local delivery.

'Relaying Denied' is a message from the SMTP server you are contacting that says its not going to send outgoing mail to other domains from servers other than itself. This is to protect it from spam, so that a rogue PC on your network can't call up the SMTP server and start spamming the internet. Those same servers often have it setup so that if you authenticate with the server (showing that you are legit hopefully) you can then relay email to the outside world through that server.

How do I run tcpdump?

See http://www.wireshark.org/. Wireshark does what tcpdump does, but also displays the captured packets nicely. For tcpdump see its manual page (if available).

--shmem

_($_=" "x(1<<5)."?\n".q·/)Oo.  G°\        /
                              /\_¯/(q    /
----------------------------  \__(m.====·.(_("always off the crowd"))."·
");sub _{s./.($e="'Itrs `mnsgdq Gdbj O`qkdq")=~y/"-y/#-z/;$e.e && print}

The web server I am using now requires authentication when sending out emails. I am sending out mass emails

The picture that comes to mind immediately is that of a clueless spammer.

What the heck are you doing? Why don't you send your mails over a proper Mail Transport Agent, administered by somebody who got the basics?

_($_=" "x(1<<5)."?\n".q·/)Oo.  G°\        /
                              /\_¯/(q    /
----------------------------  \__(m.====·.(_("always off the crowd"))."·
");sub _{s./.($e="'Itrs `mnsgdq Gdbj O`qkdq")=~y/"-y/#-z/;$e.e && print}

Perhaps not so clueless ..

M$ Internet Information Server (IIS) has 3 services built-in:

• HTTP
• FTP
• SMTP
So, typically, in a small MS environment, the web server IS the SMTP server. More typically, since servers are administered via the IIS console, which is thought of as the "web server".

     "As you get older three things happen. The first is your memory goes, and I can't remember the other two... " - Sir Norman Wisdom

I'm not sending spam. I created an email program that attaches local files on my hard drive and sends them to perspective clients daily. It's easier than uploading the files daily to the web server.