Are Hotmail cutting their own throat


Hotmail says I send Spam

Spam is a big problem for everyone. Postini estimate that spam now accounts for approximately 87% of all email on the Internet. There are several technologies that greatly reduce its penetration though, especially when used in combination. The exact technologies used by Hotmail are not clear, but if you’re having problems sending to Hotmail it might be worth having a look through their various FAQ’s, guidelines, anti-spam policies, and services aimed towards the sender. If you wade through all this and are confident your environment checks out but are still having no success sending to Hotmail, you can always contact their support staff, which is exactly what I did.

The response I got from Hotmail support was that their SmartScreen technology had identified email coming from my domain as being spam and had blocked my email server IP. Now, even if I was sending spam, somehow blacklisting the IP regardless of what other domains are sending email through that server does not seem especially “smart” to me. Hotmail support would not tell me why my domain was being flagged for spam, and when asked what the possible solutions were I was told I could sign up for 3rd party accreditation through Sender Score Certified (at a cost of $400USD start up, and $1000USD each year) who maintain the only whitelist service Hotmail use, and was also advised I could try tightening my SPF policy. Just to be especially vague the footer on the email also stated that there were no guarantees that any of the solutions offered would work. Great! So I could end up paying $1400USD to be accredited by a 3rd party whitelist just so I can send to Hotmail, and there is still no guarantee that if I get accreditation that my mail will get through.

I took the other option and tightened my SPF policy so that it explicitly stated what servers were able to send email on behalf of my domain using the “-all” option. I waited 72 hours as the hotmail support said it would take to update Hotmail’s various caches, but still I could not send emails to Hotmail. I then came across this article on openspf which pointed out that in fact the SenderID technology which Microsoft had championed (and Hotmail use) as another anti spam technology was in fact highly incompatible with SPF policies. Microsoft were apparently even made aware of this prior to the final release, but did not do anything to correct it despite there being hundreds of thousands of domains with active SPF policies in effect at the time. I updated my domain with a SenderID policy and waited another 72 hours but still the problem persisted. I contacted hotmail support again who informed me that if SmartScreen was flagging my email server IP due to a reputation issue (or lack of it) then it might take longer than 72 hours for the problem to rectify itself.


Anonymous's picture

I found a solution: :) hope it works for you

I tried to find solution on IIS part, and read the article on this page. Honestly it helped a lot.

The problem is not IIS SMTP settings. After I read here, I tried my IIS with my outlook, and hotmail received my messages. But hotmail doesn't receive messages from WEB application which is ASP.NET. God sake it is a Microsoft product.


After I added headers to my message from my ASP.Net application, hotmail started to receive my emails. I don't know how long it will continue. I just post here immediatelly, so you guys don't have to struggle like me any more.

Here is How I added headers to my outgoing email:

Dim objMail As New System.Web.Mail.MailMessage

objMail.From = ""
objMail.To = ""

objMail.Subject = "Subject line comes here"
objMail.Body = "Message body goes here"

objMail.BodyFormat = Mail.MailFormat.Text

objMail.Headers.Add("X-Mailer", "ASP.NET")
SmtpMail.SmtpServer = "My Local SMTP Server Address"


Hope it helps;

Emin Pala

Anonymous's picture

Hotmail also suddenly deletes Mac Outlook Express 5 mail !

Not only is the client the main error in hotmail's pathetic SILENT deletion of incoming mail, such as the thunderbird version you tested, but my own tests show that emial sent from an equally non-spamming small server 100% configured correctly also is lost, so long as the CLIENT email program used to create the mail is Microsofts own Mac version of the older Outlook Express 5.0

So the client creates the spam score. The same exact email sent other ways goes through.


I will direct everyone to this page to now say goodbye to hotmail.

Hotmail (which microsoft paid nearly a billion dollars for I think) is as of this month, a dead service.

Long live Yahoo (gmail is better but archives your emails).

CRAZY microsoft! What were they thinking?

I might consider trying to add a different X-Mailer header as suggested on the email server to overcome microsofts retardation.

Anonymous's picture

Me too (yes, another one)

I have what appears to be the exact same problem. Thanks for the write up!


Anonymous's picture

our hotmail experience

I've been embroiled in this hotmail cr*p for the past month.
Countless hours lost. And still no resolution.
Here are some things we've discovered:

-If a hotmail users sends an email, and the recepient replies, the email will make it through.
-There was some success with the following header:
To: "Test User{or the actual display name of the user}"
versus the usual:
-Someone in the company discovered that sending as html (Content-Type: multipart/alternative) was successful 70% of the time. Sending as text/plain went to spam folder everytime.

Anonymous's picture

My Hotmail Account

Interesting comments ab't service has been nil for weeks...while looking into the problelm, I stumbled on your site...I am an illiterate ludite..what can i do? I am taking my hard drive to an"expert" and seeing if there is any hope for me and my "toweer of power"!!!! Moreabout this later... if me and my computer survive...or it will be an Apple for me!! dont know how to sign off, except :
Hoping to communicate with you soon. BP Canada

Anonymous's picture

HotPOP Account

E-mail sent from a HotPOP account to Hotmail are also lost into oblivion.

Hotmail also stoped working with Entourage 2001and OE5 Mac. I can get e-mails but not send.

Anonymous's picture

I am having exactly the same

I am having exactly the same problem. Outlooks arrives, mutt arrives, CLI arrives, thunderbird, evolution, squirrel mail don't.

But, if I send the same email to a gmail account and hotmail account at the same time (by filling out 2 to: fields) it gets through!

Also, as you said, replying to a hotmail message also gets through.

Anonymous's picture

Same problem here...

Two months ago, i've started a few sites. Sometimes i would send out a few emails not only to test the server, but also to test some site features (formmails, newsletters,...). Those emails were sent to Hotmail and other email services (only to accounts owned by me).

Even though some mail was being marked as spam, all messages were arriving without any issues. But since September 1st, email sent to Hotmail accounts, doesn't arrive or bounces back. It simply vanishes !

All email sent to other services arrives, even though sometimes is filtered as spam.

I've asked for support from my host and they were very helpful. I really don't see any problem from their end. My SPF records are ok and my DNS report is similar to the one from the IIS Aid (everything is ok with just a few warnings).

At this time, if i send any mail from Outlook or Webmail (Squirrelmail), it simply vanishes. But if the email sent is generated by the server (from a formmail or a maillist) it's delivered... weird...

I can also confirm what other posters said, that if you send a message from Hotmail to the mail at your domain and the reply... the message is received at Hotmail without any problems.

Anonymous's picture


If you currently have commas, try removing all commas from your SPF record, especially if you have more than one domain. Then wait 3-6 hrs and then notify Hotmail of the change -

Sounds strange, but it worked for me.

Anonymous's picture

same problem here

We've got the same problem. Mail sent from TBird to msn is dropped without any bounced message eventhough the outgoing mail server identifies the messages as queued for delivery. However if the exact same message is sent with Outlook, the outgoing mail server has the exact same "message queued for delivery" message but the mail goes through no problem.