in reply to Authentication Required

Your SMTP server seems to be demanding that the SENDER be identified as a part of it's domain.

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', ....
Also, TCPDUMP may be overkill, especially if you are not familiar with it. Try DEBUG:
MIME::Lite->send('smtp','some.host',Debug=>1);
.. But I don't think that will help you. Your SMTP server has already told you what it does not like about your message.

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

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Re^2: Authentication Required
by njweatherman (Sexton) on Feb 26, 2008 at 00:57 UTC
    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.