For completeness, I researched how to configure Hotmail to use custom From addresses. Hotmail's implementation has gaps that make it the least desirable of the three email services I reviewed so far (Gmail and Yahoo Mail being the other two).
Hotmail has instructions on how to use custom From addresses but I was unable to find instructions on how to set it up. Turns out, the usage instructions were incomplete. In addition to selecting a predefined custom From address during composition, Hotmail offers "Add an email address" in the From dropdown. Choosing "Add" brings you to the setup page.
Several things I found glaringly missing or undesirable: you can't edit the alternate addresses once configured. Also, Hotmail's help (linked above) WILL add the Sender header to your mail, making your From field look like:
From: yourname@hotmail.com on behalf of custom@otherdomain.com
I was unable to find a way to suppress the Sender header and Hotmail does not offer use of external SMTP servers. I confirmed through several test messages that Hotmail does indeed add the Sender header, which MS Outlook and even Hotmail itself will interpret as "on behalf of".
On the mobile side, I found no way to originate mail from a custom address. I did not try the Gmail-style forwarding workaround as I don't use Hotmail. Any readers who test this, please comment on your experience.
2010-05-02
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I am unable to test this on platforms other than my Android phone as I don't have access to other phones. If you try this on a Blackberry, iphone, Maemo, PalmOS, Symbian (is this still around?), webOS, other mail clients, please comment on your experience. Did it work, did you need to change the procedure some, share please and help all our readers. Thanks!
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