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Why is Windows Live Hotmail rejecting email I send my friend?

Every e-mail that I have sent today to friends with a Hotmail
account has been returned saying “550 REPLY: 550 SC-004 Mail rejected
by Windows Live Hotmail for policy reasons. A block has been placed
against your IP address because we have received complaints concerning
mail coming from that IP address. If you are not an email/network admin
please contact your …” or something similar. What do I do?

Sadly, the error message is pretty self explanatory: Hotmail thinks
you are a spammer.

We’ll look at why this might be, and what steps you might take to
avoid the problem.

Note that I didn’t say “fix” the problem.

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Most email services, including Hotmail, are very secretive about the tools and rules that they use to determine what is and is not spam. While we might not like that secrecy, it’s on purpose and very important. The reason is simple: if they went public with the rules, spammers could then use that knowledge to work around those rules.

“… people have been hitting the Junk button …”

The result? More spam.

So all we can do is make some semi-educated guesses about what’s going on.

… we have received complaints …” tells me that people have been hitting the Junk button in response to email that originated at your IP address:

Windows Live Hotmail Junk Button

… mail coming from that IP address …” tells me that Windows Live Hotmail has gotten several complaints, and all of those complaints are about email that originated at your IP address. That can happen for a number of reasons:

  • You actually are sending spam.

  • You may not think what you are sending is spam, but the people you’re sending it to do. Do you forward a lot of urban legends and other “forward to all your friends” kinds of emails? That’s easily considered spam, or at least “junk” by many people.

  • Your computer might be infected with a virus that’s turning it into a spam-sending bot on a zombie network. It could be sending thousands of spam emails without you even knowing about it.

  • Your computer gets a dynamic IP address via DHCP, and a previous owner of that IP was a spammer. By randomly getting that IP address you “inherited” that spammer’s reputation.

Some of these you can control, some you cannot. Taking that same list, we can turn each into a remedy, of sorts, to avoid being flagged as a spammer:

  • Don’t send spam.

  • Don’t send email that people could reasonably flag as junk. Quit forwarding urban legends and the like.

  • Take all the steps necessary to keep your computer from being infected with malware.

  • Consider discussing IP assignment alternatives with your ISP.

Those are typically preventative measures, though, and not always something that will help you once your IP address has been blocked or other problems arisen.

One additional source of assistance and information is the “postmaster” domain on many popular email services. For example postmaster.hotmail.com is the “Windows Live Hotmail Postmaster Services”. There you’ll find topics such as “My e-mail is being blocked by Windows Live Hotmail or is being sent directly to the junk e-mail folder”. While much of the information there is technical in nature, it may be of additional help.

Not all email services have “postmaster” domains set up, but if they do it can be a quick place to get additional information for mail related issues.

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20 comments on “Why is Windows Live Hotmail rejecting email I send my friend?”

  1. I think that there might be a bug in the Hotmail Spam system. Yesterday I tried sending an email to 2 friends with hotmail accts. and I got that same message. I went to the hotmail support page to see what the problem might be and there were several people with the same problem. If M$ were really competent in their Spam filter design, they wouldn’d block all mail from an email provider.

    My email address is @gmx.net>. I’m writing that to see if others among your readers have the same email provider and hopefully all who respond to this can maybe we can all find a pattern in this.

    On the upside there is a solution, or rather a workaround. Open another freemail account and use that to send mail to your hotmail friends. And switch to Linux as Micro$oft is notorious for thinking thay know what you want better than you do. (Only kidding. As bad as M$ is, I still use it as it is the most cost effective way to get my work done.)

    Reply
  2. A friend last week sent me mail from her gmx.net account. It was rejected.

    I have tried to send mail to a hotmail account from my telkomsa.net account. These attempts have failed for some time now. This always fails when sending mail using telkomsa.net’s webmail service. It does not fail when using the same account via Outlook.

    I am becoming hesitant to use my hotmail account in case recipients are unable to reply to me.

    Reply
  3. It may not do the trick in all cases but, if you have a fixed IP address and subject to how friendly your ISP is, you may care to ask them to change it.

    Reply
  4. I had the same problem. All my e-nails were blocked by MSN, Hotmail, and Live. My server got it straightened out somehow.I now have a separate address book for those using those systems.Using Mozilla Seamonkey this is easy to do.

    Reply
  5. It seems that Hotmail finally fixed the GMX problem today after @ 10 days of complaints. Imagine, Hotmail blacklisting the largest email domain in Germany, Switzerland and Austria (if not all of Europe) and taking 10 days to fix it? MS is becomig a dinosaur.

    Reply
  6. I have problem too on Hotmail and to my frustration, Yahoo too. Have been contacting my provider but they just couldn’t provide a satisfactory solution. So I now turned to webmails.

    Reply
  7. as of april 14th I can not reply to my emails in windows live hotmail.
    It’s also not allowing me to report a problem. There is no way to contact support to solve the problem. What do I do, I have had this account for over 6 years without any problems like this.

    Reply
  8. Greetings,

    I suffer the same problem with my paid email account. I suspect that my host hosts “some” spammers who use the same IP I use.

    You can ask the windows live support team to remove your IP from their black list, I did this here and they responded with an inquiry to answer some questions about the service I use.

    Try it, this may solve your problem.

    Reply
  9. The problem came back for at least the 4 th time this month. The Window$ Deadmail people always respond that they are working on the problem, but they don’t seem very competent. GMX.net is the biggest freemail provider in Germany, Switzerland and Austria, ranked the 140th website in the world according to Alexa.

    A workaround is to open another freemail account from which you can send emails to Hotmail addresses. The solution is to have all of your friends stop using Hotmail and use a more reliable provider such as Gmail.

    Reply
  10. I am the one with the MSN hotmail account and it is my friend who has a yahoo account whose emails with attachments and even those without attachments have for the past week or so not been getting to me even though it’s been telling here her stuffhas been sent to my address. I have never experienced that problem before and she has sent me lots of stuff. HELP!

    Reply
  11. 10/08/2009 – For about a week, thru 10/06, I had ALOT of trouble with MS suddenly rejecting emails to anyone with hotmail or MSN addresses.

    I advised all those people using MSN/Hotmail that they ought to dump MS’s email system. They could lose their business relationships and clients. I wouldn’t even own an MS email address since its bound to be a source of big trouble.

    Reply
  12. My friends send email articles with multiple pictures. I go to forward those same articles on to other friends and am rejected with a note saying, “You can only have 5 attachments. Please remove some files and try again.”

    Comment: if they are signed with email suppliers that enable them to forward multiple files, I am learning which email suppliers they use, and I will sign up with those suppliers and not with you. Please change your policy.

    Sincerely,

    John O’Dell

    Reply
  13. Sorry Leo. I think you’re being a little too protective of Hotmail. I just sent an email to my grandaughter. I can assure you, I don’t send junk to her or anyone else for that matter. It was rejected. I sent her another. It contained one word “Test.” It was rejected. The email I sent her two days ago went through.
    This evening I sent out a newsletter to our club members, about 75 people. It got through to all except the four who use Hotmail. I’m sure the other 71 recipients have anti-virus scanners as well as their mail service providers.
    I have carefully read your article and have taken every precaution you mention, and have done so for years. In addition, my son is a software analyst and teacher and has written many applications. He ensures my computer is always clean. I also think you have to admit Hotmail has had serious problems in the past. A quick engine search will prove that.
    So please stop making excuses, lest people think you’re on their payroll.
    Ed

    Reply
  14. I work with this college as system admin and mails going out to hotmail.com from our domains are getting nowhere. We don’t get any NDR nor our mails reach hotmail.com. Can you assist as to what may be going wrong?

    Thanks

    Not really. This happens a lot with Hotmail. You can try the Hotmail postmaster.

    Leo
    19-Jun-2010

    Reply
  15. Hotmail sucks.

    I get e-mails to friends’ hotmail accounts blocked all the time. There is no recourse. There is nothing they can do on their end to stop this. It’s a pain in the arse to have to keep forwarding e-mails again and then have to find another way to send details and attachments to people you know.

    I hate how hotmail wastes so much of my time.

    NOBODY should use hotmail.

    Reply
  16. I use a business email account – and hotmail SUDDENLY began rejecting my emails. I am working with programmers and multiple other doctors, etc and a lot of them have hotmail. I have had to copy the emails to my PERSONAL account and they go thru. Maybe hotmail should send something to the administrator of a providor vs just cutting them off w/no notice!

    Reply
  17. when i try to send an email the top tool bar disapear an replaced with a message saying windows live hot mail was not able to complete this request

    Reply
  18. how do you solve such a problem I would like to send my emails out once again should I change my email address like hotmail trouble i understand what is going on can you rectify for me

    Reply
  19. @Gail
    Hotmail often blocks all emails coming from a particular email company. You could try contacting Hotmail’s support page, but this usually leads nowhere. One workaround, as you suggested, would be to open up a new account (I recommend GMail) to be able to email people with Hotmail accounts. Hotmail doesn’t indiscriminately reject GMail Perhaps not a clean solution, but it should work.

    Reply
  20. when is send email through my hotmail id,it is rejected . message displayed is ” Hotmail was not able to complete this request. Microsoft may contact you about any issues you report.”

    Reply

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