I was wondering. I have a site which redirects incoming mail to my normal e-mail address. But when I reply to those mails, the from field off course shows my personal e-mail address. Is it possible to send mails with a different from address? I know you can add reply-to to make sure any replied messages are again sent to the site mail, but that still shows your own address in the from field.

Don't know if this will be much help but I use this functionality in Outlook at work.

I created a mailbox for my 2nd email account (2nd work email that is) by specifying the mailbox name. I then activated the From field in the View settings. In order to send/receive I need to be set as the owner of that mailbox.

I do the same via gmail. You have to set it up in the settings, which involves gmail sending an email to the address you want to send from. You then have to click a link in the email to validate you really own the address and from then on, it's selectable in gmail.

It's also possible to manually specify the from address in any code I've ever seen that sends email (C#, php...yea, ok, I haven't seen much code). It's also possible to specify the from address if you manually send an email via telnet to an SMTP server, though in both of these cases, the mail server can be configured to not allow addresses that it doesn't control.

I try to keep my personal and work e-mail separated, so I can't help you there. God forbid one of my colleagues found out my personal e-mail...I have a long and strict selection process for colleagues who may become friends. Of course, this rule makes me very popular as these conversations take place:

Colleague: Wow I got this awesome thing you gotta see!
Me: Cool, send it to me.
Colleague: K, what's your e-mail address?
Me: What? Just look it up on the outlook address list, you know my name.
Colleague: No I mean your own e-mail address.
Me: Oh. Yeah....can't you just send it to my work address?
Colleague: *glares*

heh... I've had friends at work accidentally leak my personall address in emails cc'd to other people, which cascades into a rash of work emails going to my personal account. which pisses me off. I typically just ignore the emails, and gave the leakers some serious shit.