I don't mean to dissect your use of the English language, but do you mean to say that your system sends the messages but they don't arrive? Also, I assume that ordinary email messages created within your LAN and sent via the same SMTP sender are successful in being delivered.
In that case it is possible that something in your message is attracting the attention of a SPAM filter at the destination. Do you have a return address on your emails? Are you getting any rejection messages?
Believe it or not, Hotmail does very little to prevent SPAM from reaching the mailboxes of subscribers to their free service. Their desire is that these subscribers get fed up with the SPAM and subscribe to their paid service, which has a very effective SPAM filtering system.
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