I am helping someone migrate to an Outlook.com account from an ISP-provided POP3-enabled account. I've set up forwarding from the old account and imported their address book into their contacts list, but I can't figure out how to go about doing the last thing I'd like to do: taking a set of archived emails and getting them into a folder in the Outlook.com account, preserving the original sender name.
They have a small set of emails saved locally (a few hundred) in their mail client (Windows Live Mail) that they refer to occasionally, and I'd like to preserve that experience in their new account. Obviously, simply forwarding the email would work, but the name of the original sender wouldn't be preserved. I don't care about any of the other headers, I just want them to be able to see the original email with the correct From address, subject and text.
I have all of the saved emails as .eml files. How can I get these into Outlook.com with the sender address intact? Right now my best idea is to write a script that will pull out the text and the From address from each .eml and send them via SMTP using that From address, but I haven't fiddled with mail scripts in a while and I'm not sure if SMTP servers that let you send "as anyone" are something that exist anymore.