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

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Summary: Spam prevention methods can often lead to legitimate mail being blocked by mistake. We'll look at some of the ways to avoid it.

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.

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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Article C3696 - April 9, 2009

Recent Comments
11 Comments

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.

Posted by: MarkB at April 14, 2009 8:35 AM

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.

Posted by: Bill Chubb at April 14, 2009 10:14 AM

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.

Posted by: Gene at April 14, 2009 11:30 AM

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.

Posted by: Mark at April 14, 2009 2:17 PM

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.

Posted by: TY Tom at April 14, 2009 6:45 PM

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.

Posted by: Janice Darr at April 16, 2009 5:05 AM

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.

Posted by: Ashraf Sabry at April 17, 2009 8:32 AM

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.

Posted by: Mark at April 26, 2009 1:08 AM

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!

Posted by: Carol Hemming at April 27, 2009 3:06 AM

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.

Posted by: Jeff Epstein at October 8, 2009 12:35 PM

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