Are Hotmail cutting their own throat

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Just recently I decided to do a bit of house work on my server and DNS, and one of the things I did was do some research on SPF (Sender Policy Framework) and publish an SPF policy for my domains. However, after doing this I noticed something strange in that no emails I sent to family and friends using a Hotmail account ever received them. Nothing in their inbox or even their junk email folder, and no NDR (Non Delivery Report) was ever returned to my server. The emails just disappeared without a trace.

I scanned my email server logs and found that all the email destined for Hotmail had been successfully sent and had been queued by the Hotmail email servers, so the email was definitely disappearing at the Hotmail end of the line. After having buried myself in the problem for a good week reading every Hotmail postmaster FAQ and guideline I could find, and even contacting Hotmail support several times I still had no solution to the problem. I could not send email to any Hotmail account unless it was a reply. This got me thinking; are all free email services this hard to deal with, or is there something seriously wrong with my email environment that I have somehow missed. So I did a quick search to find the top ten free email services and proceeded to register an account with all of them to see if I could send mail to them. The results were quite surprising.

My Email Environment

Before we continue, lets step back a couple of paces and take a quick look at my email setup. For any domain this is essentially broken up into two parts, your DNS and IP settings, and then your email server itself. First, let’s look at my DNS and IP settings;

DNS & IP

  • Static IP address for my email server
  • A record of mail.iis-aid.com pointing to the IP of my email server
  • PTR (reverse DNS) record of mail.iis-aid.com for my email server IP
  • MX record pointing to the mail.iis-aid.com A record with a preference of 5
  • SPF V1 policy (TXT record) that strictly specifies which servers should be sending email from my domain
  • SPF V2/PRA policy (TXT record)

Now let’s take a look at my email server;

Email Server

  • Mail server displays host name in greeting
  • Acceptance of null sender address
  • Acceptance of postmaster address
  • Acceptance of abuse address
  • Mail server is not open relay
About the only thing my email server doesn’t do is the acceptance of domain literals (x@123.123.123.123), but very few email servers do these days since virtual domains have become so popular. For a more complete run down you can see how my email environment checks out using DNS Report. Why not check your own while there. You can also check your SPF polices are valid using Open SPF and SEO Consultants, and check for open relay at Abuse.net and Aupads.org.

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Comments

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.

Anyways:

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 = "me@mydomain.com"
objMail.To = "you@hotmail.com"

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"

SmtpMail.Send(objMail)
-----------------------------------------------------------------

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.

insane!

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!

--Dave

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:
To:
-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 Hotmail...my 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

Commas

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 -
see http://postmaster.msn.com/Guidelines.aspx

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.