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Hotmail blocking legit email

Posted by Michael Bloch in web marketing (Saturday May 5, 2007 )

If you’re having trouble sending mail to Hotmail users, i.e. the emails you send out aren’t bounced, don’t wind up in junk folders but just seem to be black-holed.. you’re not alone.

Out of the 5 billion messages sent to Hotmail addresses daily, as much as 4.5 billion are spam. These mind boggling statistics have led Hotmail to turn up the dials on their SmartScreen filtering technology with the effect of also routinely blocking legitimate email, according to this article on The Register.

A Senior Microsoft employee stated that email filtering is no longer just based on content, a sender’s email address, reputation and sender domain; thrown into the mix is the reputation of the hosting service. If your host has sites that are sending junk, your campaigns could also be affected. While this really isn’t all that new and many ISP’s also work on host reputation, what is missing from Hotmail’s approach it would seem is the generation of bounce messages that can alert a hosting company to a blacklisting.

For one sender, back and forth with Hotmail shed no light on the issues he was experiencing, even though his emails totally complied with Hotmail Technical Standards. He was told it was something in their secret sauce that they couldn’t reveal.

As a result of this kind of rabid filtering, some list owners who refuse to allow subscribers to use a Hotmail or AOL address to sign up; but I haven’t seen any data as to how this affects their subscription rates.

For some list owners, it makes more sense to use a 3rd party mailing list service who have agreements with major ISP’s whereby email sent via their services doesn’t undergo such high levels of scrutiny.

Spam filtering is a very tricky business – I know this from my work as a manager of a web hosting company. It’s such a fine line between effective filtering and too many false positives. Back things off just a tad too far and your users inboxes are inundated with spam. Added to this, spammers never rest and are constantly poking around looking for weak spots in your systems; making tweaking an ongoing task and distracting system administrators from attending to other issues.

If you’re looking for a 3rd party mailing list service that has whitelist agreements with national ISPs, consider IntelliContact – they also offer a free trial.

Is your host or ISP’s spam filtering insufficient? Getting flooded with spam? Try a free trial of an anti-spam service that will work with your existing email addresses.


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6 comments for Hotmail blocking legit email
  1. I have been having a lot of hassles with Hotmail users not receiving their confirmation emails when signing up.

    This information was very timely, thank you.

    Comment by Andrew Cullen — May 8, 2007 @ 3:52 am

  2. I’ve seen this exact same thing. I support Microsoft’s firm stand on spam, but I wish they gave options for proving legitimacy. We’ve been working with them for a couple of months now, and our email is still not getting through to Hotmail users.

    Comment by Chris Leonard — May 9, 2007 @ 2:16 pm

  3. Thanks for the good article.

    Years ago I decided that anyone who uses spam filters doesn’t really understand what they are doing.

    ISPs that use spam filters are engaging in what I would call unconscionable conduct.


    OK, spam is a problem. Spammers can make life miserable for everyone.

    BUT, an inappropriate response to spam is even worse.

    We are now getting to the stage where email can no longer be used for business communication.

    I’m not talking about mail outs. I’m talking one-to-one communications.

    I’ve never used a spam filter because I am in business – I cannot afford for a prospect’s or customer’s email to get lost.

    If spam filters worked – and by that I mean zero false positives (i.e. no legitimate email gets block) – they would be great.

    But they don’t work!

    Even though I don’t use spam filters, I don’t get spam.


    Because I use challenge-response.

    IMHO, challenge-response is the *only* valid way of stopping spam.

    Spam filters are destructive.

    Challenge-response is pretty much perfect.

    Sure, each spam generates a challenge email. Sure, ISPs might not like that.

    But ask yourself this….which is more expensive? A few more bytes across the internet or the wasting of people’s time.

    If idiots like Hotmail continue with this stupid approach, I can see the day where email is just no longer used by anyone.

    That’s one hell of a cost for all of us to pay!

    Comment by Russell Robinson — October 9, 2007 @ 2:02 am

  4. Russel, thanks for your input. I agree that challenge/response is really useful; I published an article on a service people can trial for free here:

    I guess one of the few disadvantages of it is the sender having to jump through a hoop to get their email through; but if it’s important enough, they will.. bit like double-opt-in subscriptions; if the subscriber really wants it, they’ll click the link in the confirmation email. I do see challenge/response being somewhat of an issue in a pre-sales scenario though.. that’s the time that we don’t want people having to jump through hoops. Still, there’s a way around everything.

    Comment by Michael Bloch — October 9, 2007 @ 6:14 am

  5. Good luck trying to resolve this with Hotmail. Once you submit a support ticket, trying to reply to the e-mail response you receive from them conveniently bounces back. Chat with their “Chat Support” and they’ll give you direct contacts to e-mail which ALSO bounce back. Finally, Chat Support will ask you to fill out a form, which happens to be the same exact form you already filled out and received a ticket number for. Explaining this to a chat support rep being paid $7 an hour named “Miller” or “Murray” is futile. I think the idea is that you will give up out of frustration. Awesome business model.

    I realize that I could pay for a service to have my mail delivered to Hotmail and if that’s the solution then Microsoft needs to just broadcast that to the Web community and say “If you want mail delivered here, you have to pay for an approved 3rd party service. We’re sorry we have to resort to this but it’s the only way to effectively control SPAM”. You can explain *that* to a client. Explaining mystery mail that neither gets delivered nor bounces back doesn’t sit well with paying clients.

    Google gets it right. My G-Mail is better than 99% SPAM free on the inbox, less than .1% legitimate mail in the junk folder and I have yet to have any mailed blocked from domains and clients I work with. I don’t even check the junk folder any more because of its accuracy.

    At this point I have no choice but to tell people to convert to G-Mail and then send them an invite.

    Comment by Dave Fore — May 30, 2008 @ 7:49 am

  6. Hi Dave:

    That is exactly what I am doing. When people register on my sites, I have a pop up telling them to avoid using any email account has to do with Microsoft.
    So far, no complains. I am waiting for the day Google kick them in their asses.

    Comment by Andres Perera — October 26, 2008 @ 3:15 pm

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