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m (3 Sep 2006 11:19): Since I don't have a net connection at home, these days I write emails offline to send when I periodically visit the local cafe with wireless access. But I write them in vim, and there's no good way to grab the text from the file into my gmail message text box (there's almost certainly a good way) so I've been mailing the files to my gmail address from my machine just by piping the file to mail -a from:[my_address] my_address. Only gmail thinks that because the file is from itself, but originates at the domain "localhost" at some strange ip address that the message is spam. Which, you know, is what I'd want it to do. I don't want some fucker with a linux connection at a net cafe sending me junk emails. So I've been adding a strange header line to these emails and marking all of them "not spam" when they end up in the spam folder with the hope of training my gmail to treat the ones with this particular header line as good, even though the header address stuff is clearly junk.

so far it hasn't been working. I'm hopeful.
Paul (3 Sep 2006 17:14): I'm also just starting to dabble in SMTP-from-my-machine. Sometimes yahoo marks it as spam, and sometimes not. I haven't experimented enough to tell their criteria. I think they should allow any message with valid hashcash, but I don't know if they do. One major experimenting problem is that maybe they "learn" every time I send a message what to think about my IP.
Grant (4 Sep 2006 0:02): Back when I went on a email spoofing kick to see how this stuff worked in college, I noticed that whether my fake emails would be marked as spam depended mostly on what headers it had. When I gave my email a full set of normal headers, it would get through to my hotmail account, but if I left out any of them, it wouldn't.

I'd assume that they've gotten better than that by now, but it'd be the first place I checked, if it were me. Write a message to yourself from hotmail or something, and check what all the headers are, and start putting them in your own email.
m (7 Sep 2006 2:17): Mine seems to say "Return-Path: mike@localhost" regardless. I think I need to change some exim setting to fix this. Only, what would I change it to? mike@localhost is pretty accurate (i.e. anonymous connection from some internet cafe somewhere) -- what I want is to have some header field that will tell gmail "hey, I'm okay" like, by a manual setting or something. The mail I sent from yahoo to my gmail has a DomainKey-Signature field that's long and interesting. But I bet you need a domain for that to work.

Looking at Hashcash now.
Grant (7 Sep 2006 16:59): When I was doing it, I just used PHP to do the dirty work:
mail($to, $subject, $body, $headers)
Alternatively, try specifying a different from address? Gmail might specifically mark messages that claim to be from Gmail but obviously aren't as spam.
I can't check email at work, or else I'd try this stuff myself. I never seem to remember when I get home.
m (19 Nov 2006 8:01): my account's been down for the past hour. error code 766.