External SMTP server, From address

I have googled a good number of postings about this but just couldn't quite find the right solution. Surely this can't be that hard. Running Leopard, here's what I'm trying to do:
Use Mail to read & send emails from my work server as well as my .Mac account.
Easy enough, you would think. Sorry if this is too obvious but I'm a new Mac devotee (though this has rocked my boat a bit!). So, here are the problems I've encountered:
1) Tried to add an External Server to MobileMe. Problem: Can't my external address as reply-to
2) Tried to add the account to Mail. The SMTP server doesn't seem to want to take the password that I know works for Outlook and keeps the account "Offline". When I try to send an email using this in the From, it gives me the outgoing email error, allows me to edit or select servers. Selecting it again gives the same erorr.
3) Tried to just use the default Mac SMTP server for this external account, but still get an error when trying to send.
Please help me get the right solution!
Thanks,
R

The MobileMe .mac/.me smtp can only be used when sending from a MobileMe address, and not any others.
What is the source of the SMTP you are trying to use with the other account? What Port are you presenting that SMTP on, and how have you selected to authenticate it?
Ernie

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