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Sending Mail to Hotmail Users? 126

Posted by Cliff from the ham-not-spam dept.
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?"
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Sending Mail to Hotmail Users? More

Sending Mail to Hotmail Users?

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  • See slashdot article... (Score:3, Informative)

    by crazyjeremy ( 857410 ) * on Thursday June 22, 2006 @09:38PM (#15586689) Homepage Journal
    Did you see this article? http://yro.slashdot.org/yro/04/05/05/1237245.shtml [slashdot.org]?
    Also, have you tried sending the email spoofing the receivers email address? You can set the "from" header to their own address. Of course, this won't help ip based whitelists, but it will help many emails make it through for some mail hosts (few users block their own email address)

    • Re:See slashdot article... (Score:5, Informative)

      by Spazmania ( 174582 ) on Thursday June 22, 2006 @09:40PM (#15586696) Homepage
      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.

      • (a) IN GENERAL- Whoever, in or affecting interstate or foreign commerce, knowingly--
        ...
        (3) materially falsifies header information in multiple commercial electronic mail messages and intentionally initiates the transmission of such messages,

        So, it's only illegal if it's for commercial purposes, and unless I'm reading it wrong, you're fine even then as long as it's within your state and the affected business is also within state.

        • IANAL and I'm betting YANAL either, so I would hesitate to take any advice such as this from someone of our ilk (non-lawyers). I wouldn't be willing to bet against an argument that the sending server and the receiving server were in different states, therefore it's interstate traffic. Given that Hotmail's servers could be just about anywhere, well...
        • unless I'm reading it wrong

          You're reading it wrong.

          "Whoever, in or affecting interstate or foreign commerce, knowingly" is pretty close to boilerplate. Judicial precedent has interpreted it to mean "virtually everything except for very rare circumstances where there is no possible tangential connection that pushes it over state lines." A grain of sand is covered in this language because it could reasonably be caught in someone's shoe and carried to another state. No, really, how do you think the EPA gets it
        • I think the "materially" part could be an excuse in this situation. It seems immaterial if an email to someone who asked for it, has the from header changed. But then the word "materially" probably has a precise legal definition. If you're not doing anything crooked I don't think a prosecutor would waste time on it. I don't think a jury would find against you either.

          As for the interstate commerce part, some courts have basically found that when you thought about the act, your brain waves may have bounced

      • Automatic death sentence (Score:5, Interesting)

        by coyote-san ( 38515 ) on Friday June 23, 2006 @12:00AM (#15587256)
        Falsifying headers is illegal, but I doubt anyone will actually pursue a small-time website operator who's sending otherwise legitimate traffic.

        But for many of us forging headers is an automatic death sentence. I've walked away from existing business relationships where I had non-refundable credits because a customer support request was answered with a forged header.

        On the other side of the table, it's one of the few actions where I would not hestiate to recommend immediate termination for cause if I caught a member of our staff pulling that stunt. (The other actions are using the computers to perform illegal acts or to distribute pr0n/warez.)

        The reason it's so serious? It shows a culture that has a casual disregard to the consequences of identity fraud. If you forge mail that appears to come from me, then who else are you sending those forged messages to? Why should I believe your answer? Trust, once lost, is not easily recovered.

        (BTW this doesn't even address the original point of getting past spam filters. Like many sites I have my MTA set up to reject incoming messages that claim (in the envelope) to come from my own domains. I know who I am and anyone claiming to be 'me' is, prima facie, making fradulent claims and should be treated accordingly. The last time I checked that test, by itself, was blocking about a third of inbound traffic.)
        • 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.
        • I have my MTA set up to reject incoming messages that claim (in the envelope) to come from my own domains. I know who I am and anyone claiming to be 'me' is, prima facie, making fradulent claims and should be treated accordingly.

          Maybe I'm not understanding the level this occurs at, but doesn't that lock out any of your employees sending work email from a home account using their work return address? Or an employee without VPN access emailing the company from the road?

          • Maybe I'm not understanding the level this occurs at, but doesn't that lock out any of your employees sending work email from a home account using their work return address? Or an employee without VPN access emailing the company from the road?

            Why are employees sending work emails from a home account? Offer them a HTTPS webmail server to deal with those cases. (IOW, there are technical fixes for the border cases such as webmail, VPN, 800 number dial-up access or using a dial-up ISP account.)

            Don't some

            • Why are employees sending work emails from a home account? Offer them a HTTPS webmail server to deal with those cases.

              There's plenty of small businesses that can't afford a HTTPS webmail server, or even an authenticated SMTP server. It's not that uncommon for these businesses to have people working from home, so there's a legitimate need to have the from: address be the business address, even though the email wasn't sent from the business, or one of the businesses computers.

              Is that "forgery"? Frankly I do
              • I dunno, I'd consider $10/mo for 30 accounts (JTL [jtlnet.com]) plus web space with POP/IMAP access in addition to the webmail client to be pretty cheap. Or the Small Business package at A2 [a2hosting.com] which is only $8/mo for web space, IMAP/POP3/SMTP. Or FuseMail [fusemail.com] which is a little more expensive but has a nicer web interface.

                Heck, one of the A2 plans is only $3/mo.

                Some hosting companies even thrown in spam/virus filtering for free.
                • That's certainly a solution, but there's a lot of small businesses that're using Exchange or similar on-site email. IMAP/pop/SMTP doesn't provide the same functionality as Exchange. Even if it did, transitioning isn't free and certainly wouldn't be warranted just to solve the non-problem of employees changing the from: header on their home computer.

            • Offer them a HTTPS webmail server to deal with those cases.

              This kind of "medicine" is worse, than the decease. There are two modern e-mail protocols: IMAP for reading, and SMTP for sending.

              Various "Webmail" implemements are nothing but either excuses for advertisers (like Google, MSN, Yahoo! "e-mail" services), or hacks and works around moronic firewall policies.

              As I say in the subject, there is no "Mail" in Hyper Text Transfer Protocol...

              What you wanted to write, was something like:

              Tell them to u

      • Haha really? I do that all the time... well, sometimes.

        It's easy with PHP mail() because it's just one parameter
      • Never do this. Forging the return address is one of the few things that actually is illegal.

        Regardless of the legality of it, most people with spam filters have them configured to block email that comes from an external source using an internal address, so I doubt that would help any. I know that everywhere I have ever worked had such messages blocked.

    • Re:See slashdot article... (Score:5, Informative)

      by Violet Null ( 452694 ) on Thursday June 22, 2006 @09:41PM (#15586700)
      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.
      • 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 certainl
        • Actually I have encoutered one example: emails to colleagues at the government research laboratory where I work are sometimes rejected, depending on which server they happen to go through, if I use my laboratory email address in my From: header but am mailing from outside the lab (the server's error message complains about "spoof" email and specifically mentions the From: header). I don't know if they are using a custom made system here or (more likely) it's some off-the-shelf server product.
    • As far as I know, hotmail has 2 options for filtering your mail. You can either have them filter it with the spam filters, or you can have it set up to only receive mail from people in your address book. I currently use the first option, as I don't like unexpected email going in my junkbox. The result is hundreds of spam messages that get through the filter. I don't know why they can't get it right. My yahoo mail account doesn't use a white list, and blocks 99.9% of spam. I get maybe 1 spam message ev
      • Yahoo spam filter is not that great. I use my account for everything I sign up for since I know that my email addresses will get sold out by sites anyways. Looking right now I have 1310 spam in my yahoo junk mail folder, and usually get 10-20 in my inbox every few days. No matter where you go you will always get spam.
        • Well, it keeps your junk mail around for 1 month, assuming 30 days in a month, you get 43 messages blocked every day. And if you get 5 spam messages in you inbox (15 every 3 days) then I would say that Yahoo isn't doing too good a job. Hotmail on the other hand is much worse. 75% of it gets to your inbox. The only thing even resembling spam that shows up in my yahoo inbox is product announcements that I signed up for a long time ago, and don't bother to unsubscribe from. You will always get spam, but

    • Re:See slashdot article... (Score:3, Informative)

      by kv9 ( 697238 )
      i had the exact same problem with yahoo mail ending up in the bulk folder (mailserver ip was X-YahooFilteredBulk). it was easily fixed by contacting support and filling out a hefty form. so, your best bet is (surprisingly enough) tech support. i'm sure even MS has people that can help you with that.
    • I'm one of those Hotmail users that's filtered his own email address, filtering it into my Suspicious emails folder.

  • Tools are available (Score:5, Informative)

    by Anonymous Coward on Thursday June 22, 2006 @09:41PM (#15586698)
    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/ [msn.com]
    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/ [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.

  • Do yourself a favour (Score:5, Informative)

    by Bogtha ( 906264 ) on Thursday June 22, 2006 @09:47PM (#15586723)

    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.

    • Why bother? I mean, what user is worth keeping who isn't "computer-savvy" enough to understand what a Junk Mail folder is?

      While you're at it, send them all Gmail invites, and explain to them that it's Hotmail's fault for treating their mail as spam. Tell them how to give feedback to Hotmail about that particular mail. It's a lot easier to let your shock troops^W^Wusers complain for you than it is to try to deal with Microsoft.

      • Re:Do yourself a favour (Score:4, Insightful)

        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?

        • 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.

          How about this;

          You know how some people have a sign on their letterbox saying 'no circulars'?

          Well imagine if the people who delivered 'circulars' actually respected this.

          Now imagine having two letterboxes, one labelled 'circulars only'.

          So if you ask someone to send you a newsletter and you don't find it
          delivered in your regular mailbox, where would you look

  • Add a SPF record. (Score:5, Informative)

    by Utopia ( 149375 ) on Thursday June 22, 2006 @09:47PM (#15586729)
    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/ [microsoft.com]

    &
    http://openspf.org/wizard.html [openspf.org]

    • Re:Add a SPF record. (Score:2, Informative)

      by Keeper ( 56691 )
      I'll second that. Awhile back there was a big broohaha about how Hotmail was going to crank up the sensativity of spam filters run on mail from domains without SPF records.
    • My domain has a SPF record but my emails are still being marked as spam.
    • Same here, I publish a very restricted SPF record for my personal domains and a more relaxed one for the work domains. Some of the work domains have very strict options though (since they're used by more technical users).

      As long as you control the mail servers for your domain, why not publish SPF records? (Note that SPF is about anti-forgery, not anti-spam.)
  • Punch them in the face for using hotmail and get them a REAL email account. No, but seriously... I don't know if there's any (reasonable) way you're going to easily get around hotmail's "security". You could try contacting hotmail support about the problem... lord knows how much good that will do you :D. You could find a trusted host that it accepts links from, set up a mail account there, and have the mail automatically forwarded (though if you don't want it to be a mass [i.e. all the same] email you wo
    • `A REAL email account'... what's that? Are you just Microsoft bashing again, or do you think that everybody should have a proper POP3/IMAP account with their ISP? Webmail is unavoidable these days; I personally use my gmail account exclusively. If your problem is with Hotmail specifically, then I'm not sure why. Hotmail is one of the more old-fashioned webmail systems (Yahoo and gmail are much nicer in terms of UI) but there are far far more dodgy and poor webmail systems out there. I'm sure somebody w
      • I myself use yahoomail (was going gmail but my yahoo account is 11 years old so everyone knows it -- plus I have no need for the gmail amounts of storage) and I have no problems with webmail (not even hotmail, except when MS was a bag of douche and routed gmail invites to the spam folder) -- I was jokingly referring to getting them all SMTP/POP3/etc server/accounts of their own.
        • > Punch them in the face for using hotmail and get them a REAL email account.

          Yeah, right. I've had a Hotmail Plus account ($20/yr for a 2GB Inbox, no ads, offline access) for some time now (before Gmail was launched), and I must say bar some real idiocy on the part of MS I'm going to keep renewing, primarily for the spam protection (2-3 a day) and good customer service.

          > I myself use yahoomail

          Right now Yahoo's name == mud with me because they deactivated my Yahoo Mail account for 'non-use' (and delet
          • they deactivated my Yahoo Mail account for 'non-use' (and deleted all my email).

            If you pick a category of ads for Yahoo to send you, they will also let you use then POP3 to retrieve your email, which counts as a login. I haven't actually logged into my Yahoo webmail account for years but daily connections from my email client keep it from being deleted.
      • https://www.fastmail.fm/ [fastmail.fm]

        SSL { Webmail / IMAP / POP3 }

  • if they're producing false positives, they're doing a disservice to their customers. Their problem, not yours. Eventually their customers will figure it out and leave.
    • I don't really agree. many of the non-technical people I have dealt with are so afraid of trying anything new that they will deal with somthing even as extreme as this. If you cannot check your spam folder, I doubt you can set up another email account (as a son/ daughter probly set this one up for them). Why do you think AOL still has coustomers when you can get almost everything they offer for free elsewhere? because they got people hooked early on, when there was not many choices. Prehaps if enough peo
    • no they won't, they'll leave his company because they have an un-natural level of trust in MS. Some people think that MS can do no wrong, and they are the majority of computer users...

  • Very big assumptions. (Score:5, Insightful)

    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.
    • Ditto. For one example, if your MTA does not have correct delivery retry settings you'll get "blocked" by certain anti-spam methods. I've run into the issue several times where someone thought it was a good idea to set their retry interval to under *five minutes* even though their delay notification was still set to four hours! It tried delivery twice in five minute then gave up. Heck, forget anti-Spam, that might not even get you into a heavily loaded server. Obviously they didn't really know what they we

    • Exactly. When I need to do a mass-mailing from my PHP apps, I use a custom class that emulates some of the sendmail interface by opening a socket to a SMTP host. See 'fsockopen' in the PHP docs -- SMTP is super-simple, and if you want, I'll share my class source with you.

      You just have to make sure that your production server has a trusted connection to the MTA, or write a few lines of code to authenticate against the server. Also remember that one thing that really pisses SPAM filters off is when you tr

    • They won't tell you. Like so much else at Microsoft, they use security-through-obscurity for their spam filter too. Pretty much all they do is suggest paying money and screwing around with your DNS [tesco.net].
    • A big one that a lot of sites miss is mismatch between what the IP address reverses to, what the hostname resolves to, and what hostname the MTA says it is. If my MTA says 'Hey, I'm foo.example.com', but my IP address reverses to jack.hostingcompany.com and jack.hostingcompany.com resolves to a different IP address, then some servers are going to say 'yeah right' and either reject messages outright, or flag them as high-risk for spam. I've seen issues with mail servers I've set up where mail was getting rej

  • Trial and error works. (Score:5, Insightful)

    by The MAZZTer ( 911996 ) <(megazzt) (at) (gmail.com)> 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.
    • I don't know a great deal about how various filtering algorithms work, and even less about the filtering that hotmail has in place, so if I'm completely on the wrong track on this, then someone more in the know please set me strait
      That said, I think that if you do this, you should be aware that I think that if you send out emails marked as junk, then future emails are more likely to be marked as junk. As I understand it, a lot of spam filters work by assigning various point values to different things in t
    • I did. I created two Hotmail accounts for testing. I tried sending mails from PHP using the mail() function and through the PHPMailer library (http://phpmailer.sf.net/ [sf.net]). I also tried sending mails through Thunderbird and through my hosting service's webmail interface. My messages always have been marked as spam.

  • It's Probably Your Headers (Score:3, Informative)

    by Anonymous Coward on Thursday June 22, 2006 @10:14PM (#15586839)
    I've noticed that Hotmail is very particular about the headers you send along with the message. If you send the message as a content-type: text/plain and specify a valid Message-ID, it should get through. Here is what I use for extra headers:

    $PlainMailHeaders= "MIME-Version: 1.0\r\n"
    . "Content-Type: text/plain\r\n"
    . "Content-Transfer-Encoding: 7bit\r\n" ."Message-ID: \r\n";

    Hope it helps.

  • Helpful suggestions (Score:3, Informative)

    by Spazmania ( 174582 ) on Thursday June 22, 2006 @10:21PM (#15586862) Homepage
    1. Publish an SPF record. For a custom setup like yours, you can choose a subdomain just for your application and publish a record just for it, even if you don't want to use SPF for the main domain.

    2. Process the bounces. Hotmail notices and ranks the source accordingly.

    3. Make sure the reverse DNS for your server matches the forward DNS and that both resolve to a server name that is not obviously a dynamic IP address. Mail from a machine named customer43.dsl.bigisp.com tends to get weighted as spam for reasons which should be obvious.
  • 1. Obtain a Hotmail, Gmail, or Yahoo! email account.
    2. Code PHP to send emails through it to your Hotmail customers.
  • Anyone else ever find themselves without a route to any of hotmail's MXes? Once or twice per month, my mail server can't make a connection to any of the hotmail MXes. The outage typically lasts 12-72 hours, but never long enough to cause a bounce (5 days). I run tcptraceroute to port 25, and it dies at a msn.net router (the last hop that responds is 207.46.37.161). I'm on a Tier-1 ISP (Internap) sending 500-1500 messages daily to hotmail (and another 10-15k to other ISPs, with no problem). I submit to Hotma
    • I bet they happen after MS releases a patch. The servers are rebooting! Come on, we all know the drill!
    • Aha! It started happening this morning! What the hell!?!?

      Tracing the path to 65.54.245.72 on TCP port 25 (smtp), 20 hops max ...
      3 core2.ge0-0-0-bbnet1.sef.pnap.net (63.251.160.2) 0.583 ms 0.609 ms 0.741 ms
      4 10ge-3-3.r01.sttlwa01.us.bb.verio.net (209.168.94.241) 0.627 ms 0.560 ms 0.574 ms
      5 129.250.8.66 176.046 ms 1.564 ms 0.629 ms
      6 ten8-3.wst-76cb-1a.ntwk.msn.net (207.46.35.105) 171.988 ms 0.891 ms 200.322 ms
      7 pos4-1.pax-76cb-1a.ntwk.msn.net (207.46.33

  • My inbox (Score:5, Funny)

    by Anonymous Coward on Thursday June 22, 2006 @10:31PM (#15586907)
    My hotmail inbox seems to only get mail about c14lis and v14gra. Perhaps you should use these keywords in your mail to help it get through?
  • A site I developed was having similar problems. In the end we had a confimation page that said that a reply was being sent automatically, and if they didn't receive a message, then to add the site address to their contact list and try again.
  • Why not just let them enter another, in addition to Hotmail? Maybe Google could set you up with infinite invites. I bet losing traffic to Google would get them to whitelist you post-haste.
  • I have never had a problem getting an automated response for a sign up verification. I get maybe 5-10 unsolicited spams a day (all of which go directly to a junk mail folder) and 20+ solicited spams (email lists, tech groups, companies I deal with, etc...) emails a day (once again, it all goes to junk mail).

    So while other user's may have problems, I guess I'm just lucky and I've never really had a problem with Hotmail. To the extent that it has been my primary email provider since '97 (pre-MS days).

    -Rick

  • From someone who knows... (Score:1, Insightful)

    by Anonymous Coward
    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: http://postmaster.msn.com/Services.aspx#JMRPP [msn.com]

    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 d
  • You can do what FEMA does on their Independent Study Program - after you sumbit information, they display on the confirmation page something to the effect of "Users of Hotmail, Yahoo... please add the following address to your whitelist."
  • I've noticed a lot of signups don't allow you to use free email services like Hotmail, GMail, Yahoo, etc for your email address. Force them to use their ISPs' address.
    • The only problem with this is that I don't have an ISP address. I buy my internet access as a 'business' account from my telco, which includes JUST the DSL signal, an IP address, and usage of their DNS for lookup purposes.

      I have my own personal domain, as well as owning a small business, and having a domain for it.

      Most sites that block free email also block my domains, since they don't recognize them as belonging to an ISP. Both domains are hosted by other companies, neither one a 'free email' domain. So
    • 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.
      • From what I've seen, nearly everyone has a real email account. I ran an ecommerce site for a while where I blacklisted all free email accounts as well as any email account or purchase that routed back to AOL. Those two restrictions cut the fraud down to almost nothing. I can't remember a single case where someone complained about the restriction and found they had no "real" email account they could use. A lot of people would use their work email. I did wonder if banning AOL entirely was a bit much, but
        • Ditto here, we blocked all the free email providers once we realized pretty much all our fraud orders were using them and few if any legit signups used them. Gave up forwarding to the free providers abuse departments as well.
  • I've been using a Hotmail account for about 9 years now... things were okay until Microsoft took over control. My experiences have varied after MS came in:
    1. For the first year, 90% junk mails, only 10% proper mails.
    2. For the second to fourth years, 50 - 50.
    3. Three years back, proper mails got landed in the Junk mail folder, and junk mail in the Inbox... that's when David Coursey's (Chief Microsoft aplogist, then at ZDNet Anchordesk) mail got delivered in the Junk folder.... on second thoughts it seems sorta right now!
    4. I lost interest a year ago, just 2MB box-size.. didn't check my account - and boom! all mails lost.
    5. NOW: There's more than 25 MB, but it's been months since I checked my hotmail. Not much spam, but I've lost interest after getting a gmail account.

    Short answer to your question: You're better off writing a utility that swaps Junk mail and the Inbox for hotmail users. Microsoft doesn't like PHP. Open up PHP and email in google, you'll find 100s of pages of Vulnerabilities, BEFORE coming to the functionality.
    • > 4. I lost interest a year ago, just 2MB box-size.. didn't check my account - and boom! all mails
      > lost.
      > 5. NOW: There's more than 25 MB, but it's been months since I checked my hotmail. Not much spam,
      > but I've lost interest after getting a gmail account.

      Keep checking your Gmail account if you don't want to lose everything. Once every 9 months, I think it is.

      OH, and spam filtering in Gmail has got a *lot* worse in the last couple of months. It used to be faultless, but now I get 5 or 10 spam
  • Two things :

    - Make sure you have a PTR record correctly set to your hostname so that reverse lookup work. Whoever have been assigned the block from which your IP is taken (most likely, your ISP) is the one to contact for that.

    - Make sure the HELO/EHLO greeting of your MTA match the FQDN in the PTR record for the IP your mail appear to be coming from. In other words, make sure the hostname is set correctly on your mail server.

    Sorry for the elitism, but if you don't quite understand the above, maybe you sho

  • simple (Score:2, Insightful)

    by firebus ( 49468 )
    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
    • don't require users to activate the account via email. 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.

      I disagree! Activation is very important! With

  • Comment removed (Score:3, Informative)

    by account_deleted ( 4530225 ) on Friday June 23, 2006 @02:44AM (#15587802)
    Comment removed based on user account deletion
  • It has a user registration system that sends a link via email to activate new accounts.

    Some ways of flagging spam involve analysing the content to see if it looks like a spam email. Does your email just contain a link, or a link and a very small amount of text? If so this could be one reason it is flagged as junk.

    Try adding some more infromative text (e.g. Welcome text, eplanation, help) and see if this helps any. As the email filter may well score emails to see if they qualify as spam, this may help you

  • Maybe your signup message/test messages look too much like spam? Try to avoid use of exclamation marks, mispellings, ALL CAPS, etc.

    We have an e-commerce package that sends emails to HoTMaiL, AOL mail, yahoo, gmail and lots more fine using nothing more than the PHPMailer class.

    One quick suggestion, do you use PHPMailer with the mail method or with the smtp method? We use smtp as using the PHP mail() function does sometimes end up getting you flagged as spam, no idea why though! PHPMailers SMTP client

  • The situation is actually MUCH worse than that (Score:3, Interesting)

    by robosmurf ( 33876 ) on Friday June 23, 2006 @06:01AM (#15588295)
    Actually, sending mail to Hotmail is much worse than that.

    The Symantec BrightMail filters that Hotmail uses will silently delete mail. The sender will see no indication that the mail failed, but the message will be deleted; it will NOT necessarily appear in the Junk Mail folder.

    I've been using Hotmail for years, but have recently been having terrible trouble with it losing messages from mailing lists that I am on, even with spam protection set at its lowest level.

    Hotmail is NOT a reliable email system.

    As far as I can tell, the only real solution to this is to tell your recipients not to use Hotmail.
  • I expect you're on a shared server.

    Stupid blacklists seem to blacklist by IP (or sometimes IP range!) instead of domain, which means that if one spammer is using your box, then all domains on that box will get blacklisted.

    This is why my Email gets marked as spam by Yahoo. Sometimes it happens due to reverse DNS too (if you don't have complete control of your DNS, your reverse lookup may be a different domain - usually your host or ISP).

    The best option is to colocate your own server, but it's too pricey for
  • I've had this issue with Hotmail and AOL users. Once I put in the SPF record in the DNS, all mail went through.
    http://www.openspf.org/ [openspf.org]
  • I get several emails from "University of Phoenix" a week, always mark them as junk, but Hotmail's filter never seems to learn how to recognize them. Makes me wonder what do they actually do with the messages flagged as junk? Seems like all they do is move them into your junk folder, and do not update any recognition capabilities based on that... In fact, I get dozens of repeat spams a week that I all mark as junk and the filter never gets any better. I've concluded that the Hotmail spam filter is next to

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