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Sending Mail to Hotmail Users?

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 hotmail.com itself, gmail.com, yahoo.com, msn.com, 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?"

6 of 126 comments (clear)

  1. Re:See slashdot article... by Spazmania · · Score: 5, Informative

    Also, have you tried sending the email spoofing the receivers email address?

    Never do this. Forging the return address is one of the few things that actually is illegal.

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    Moderating "-1, Disagree" is simple censorship. Have the guts to post your opinion.
  2. Tools are available by Anonymous Coward · · Score: 5, Informative

    Welcome to my world. I work on email deliverability for a financial services company, so no, I'm not a spammer. Hotmail makes two tools available to you to help you get your email delivered:

    MSN Smart Network Data Services: http://postmaster.msn.com/snds/
    This will let you put in your SMTP's IP address and it will give you consolidated stats on how much mail was received, and how much was filtered as spam.

    Sender Score Certified: http://www.senderscorecertified.com/
    This company will "certify" you as a safe sender, and Hotmail will let your emails in unfiltered. The catch is you have to pay for this.

    Good luck. It isn't easy, but at least there are some tools at your use.

  3. Re:See slashdot article... by Violet+Null · · Score: 4, Informative

    I've run into this same sort of problem, and I've discovered that spoofing the from address is a really, really bad idea; there's a sizable chunk of mailservers that will reverse DNS the IP address they're receiving the email from, and if it doesn't match the domain in the from address, they'll reject it.

  4. Do yourself a favour by Bogtha · · Score: 4, Informative

    Grab something like SpamAssassin, and set it up to add headers telling you what rules have been triggered. Then send an email from your web application to that account, and examine the headers. While Hotmail probably don't use the exact same rules as SpamAssassin, it's an easy way to spot obvious stuff for you to fix. For example, using too much HTML, particular phrases, too many capital letters, being on blacklists, etc, can all be remedied by you without Microsoft's involvement.

    I also seem to remember that Hotmail strongly discriminates against senders who don't have SPF set up, so it's probably a good idea to enable that for your domain.

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    Bogtha Bogtha Bogtha
  5. Add a SPF record. by Utopia · · Score: 4, Informative

    My domain has a SPF record and I never had issues sending email to anyone on hotmail or other services.

    See:
    http://www.microsoft.com/mscorp/safety/content/tec hnologies/senderid/wizard/

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    http://openspf.org/wizard.html