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Sending Mail to Hotmail Users? 126

Cafesolo wonders: "I'm developing a web application using PHP. It has a user registration system that sends a link via email to activate new accounts. I've found that sending mails to Hotmail accounts is very difficult, because the spam filter is very strong and it filters lots of non-junk messages. I think the spam filter blocks any email whose domain isn't in an internal whitelist (which might contain popular domains, like itself,,,, etc). Most of my users have Hotmail emails. I can't simply tell my users to read the junk folder because most of them are not computer-savvy and that seems to be a bit confusing to them. Has anyone managed to solve this problem? Did somebody try to contact Microsoft? Is there any way to get whitelisted? Can an independent programmer get his domain whitelisted?"
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Sending Mail to Hotmail Users?

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  • by Vellmont ( 569020 ) on Thursday June 22, 2006 @10:03PM (#15586797) Homepage
    You sound like you're making some very large assumptions about what's actually triggering the spam filters at hotmail. What makes you think it's your domain, and not the crappy MTA you're using? Spammers often use non-standard MTAs that anti-spam programs have learned to identify through header analysis. Have you tested sending mail from a standard mailer like sendmail or postfix to a hotmail account? You obviously need to confirm what's actually causing hotmail to tag your mail as spam and stop making assumptions.
  • by The MAZZTer ( 911996 ) <<megazzt> <at> <>> on Thursday June 22, 2006 @10:05PM (#15586803) Homepage
    Get yourself a hotmail account and have PHP fire off e-mails to it. Tweak as needed until you get one through that's not marked as spam.
  • by dtdns ( 559328 ) on Thursday June 22, 2006 @10:20PM (#15586857) Homepage
    I agree that there are a lot of mail servers that reverse the IP address, but comparing the domain in the reverse entry to the domain in the SMTP FROM command or the From header doesn't make much sense. Any e-mail coming from a legitimate hosting company (like the one I work for) would be blocked. The reverse DNS entry for our IP address is valid and that host resolves back to the IP address (which is how it's supposed to be), but our e-mail server houses mail for upwards of 400 domain names. We certainly do not have a dedicated IP address and reverse entry for each domain. All outgoing e-mail leaves through the same IP address and I cannot recall a time when mail has ever been rejected because the FROM domin didn't match our reverse DNS entry. Sure, the reverse should resolve back to itself, and it's a good idea to have an MX record for the domain pointing to that host (but not required), but I think you're stretching a bit on that last part of your response. I'm sure there is some dumbass out there doing that, but likely few and far between. I'll bet they don't get a lot of mail, legitimate or otherwise based on that thinking.
  • by Bogtha ( 906264 ) on Thursday June 22, 2006 @10:55PM (#15587019)

    what user is worth keeping who isn't "computer-savvy" enough to understand what a Junk Mail folder is?

    The kind of user that pays you money? And there are a lot of people that don't understand spam filtering. Unlike most other email concepts, this one doesn't really have a snail-mail analogue.

    send them all Gmail invites

    I already do this. Without fail, every single Hotmail user that I have sent an invite to has either signed up and not switched, or not bothered signing up at all. Hotmail users are happy with crap. Think about it - if they weren't, they wouldn't be with Hotmail in the first place, would they?

  • by Anonymous Coward on Thursday June 22, 2006 @11:02PM (#15587045)
    I work for an ESP, and frankly, I spend all day making sure people don't get things they don't want...

    Domain Keys are also an excellent addition to having SPF. Different people trust different technologies, so using both is always a good idea.

    To increase your chances of mail delivery to Hotmail, have a look at this: []

    You'll figure out why your messages are being junked. Most of the biggies have some sort of feedback loop/whitelisting procedure. If you business depends on these people recieving your mail, you're doing stakeholders a terrible disservice in not using them.

  • by TopShelf ( 92521 ) on Thursday June 22, 2006 @11:14PM (#15587093) Homepage Journal
    Hotmail is perfectly fine, it's just that the parent of this thread made it sound like a service could guarantee that this guy's message could get into user's Inboxes. Hotmail has the option of having a whitelist-only Inbox, so I was pointing out that those services won't do.
  • by horn_in_gb ( 856751 ) on Friday June 23, 2006 @12:07AM (#15587277)
    I don't know this guy's target audience, but a whole lot of people don't have an ISP but still get on the net at public terminals (library, school, net cafes). They rely on free email services to have a net presence, and I think it would be sad to discriminate against them for that.
  • simple (Score:2, Insightful)

    by firebus ( 49468 ) on Friday June 23, 2006 @01:28AM (#15587577) Homepage
    don't require users to activate the account via email.

    i work on a medium sized, event driven, community website, and year after year we had the same problem - tons of people signing up at once, and a sizeable percentage of them wouldn't receive an activation email no matter how hard they tried.

    this led to much customer support.

    so we stopped requiring activation.

    and it hasn't been a problem.

    when you think about it, activation is useless. what benefit do you get out of it? you proved that some guy had access to some email account at single point of time in the past. so what? anyone who wants to get an account can sidestep your activation requirement with a throwaway email address. you're putting up a barrier to your less technically inclined customers without providing ANY benefit in return.
  • by takeya ( 825259 ) on Friday June 23, 2006 @07:00AM (#15588424) Journal
    Falsifying headers is illegal, but I doubt anyone will actually pursue a small-time website operator who's sending otherwise legitimate traffic.

    We are talking about microsoft here. The company policy seems to be take out the little guys first.

"The pyramid is opening!" "Which one?" "The one with the ever-widening hole in it!" -- The Firesign Theatre