Hi,
Please note my comments below
When you send an email it lists 2 different From: addresses?-- NO, it shows up only one address in the FROM field for each email. Two emails with two different FROM: i.e. my yahoo & hotmail ids in the "sent items of HOTMAIL ID." Sometimes, i receive reply on yahoo instead of hotmail though i have intended to use hotmail id for sending. It happens because email has been sent via yahoo id as well unknowingly.
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Is the problem that you are trying to send as Yahoo through Hotmail or as Hotmail through Yahoo services?-- NO
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Some email services rewrite the From: based on the username you use to authenticate as to use their SMTP relay (outgoing mail server) service.
What From: are you trying to use and what is the SMTP server setting associated with that account?-- Hotmail ID, Setting is- smtp-mail.outlook.com, Port- 587