Are Hotmail cutting their own throat

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Just recently I decided to do a bit of house work on my website hosting 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.

Comments

Anonymous's picture

Same problem...

I cant send emails to any hotmail account...
I figured out that hotmail blacklisted my ip, domain, and/or email...

The thing that allows the replies to work is a header in the response mail taken from the original mail that is:
References:

If this reference is equal to the email previous send it passes with out problems...

If you are blacklisted and you have to send a email to a hotmail account the only way is opening a hotmail account and send the email.

If you want that your email appears from your usually email you can change the "Reply-To Address" in the options (Message Replies)

Well, my conclusion, hotmail SUCKS.
Octavio.

Anonymous's picture

Same Problem with my accounts also

I am hosting provider, and my setup is the same, I loose a lot of time in reading their troubleshootings, and submiting them tickets, and finally there is no result.

If you create an account:

xxxxxx@mail.iis-aid.com
Hotmail will receive it without problem, because of existing PTR (reverse DNS)

But it is impossible to configureall virtual server domains that are hosted from one IP with PTR (reverse DNS),bBecause for one IP there is one domain name, so all Virtual Architectires will be silently not deleivered by Hotmail.
So Hotmail really SUCKS.

Brashquido's picture

Yeah, I think before too

Yeah, I think before too long Microsoft will have take a step back from this or it will hurt them. Non delivered mail with and NDR is one thing, but when a considerable amount of email disappears into the ether it will damage users trust in their services, and when they lose that custom it will be very hard to get it back. Since writing this article I've done some poking around the web, and it is amazing just how many other people are having issues with Hotmail since late last year.

Anonymous's picture

Absurd

I just experienced the same issue you described. I own a personal domain, to help keep my skills in check, and use it to maintain contact with friends and family. My SPF record is rock-solid, and no one has any issues receiving mail from my domain except Hotmail/MSN.

I jumped through the same hoops, and received the identical canned response from Microsoft support, recommending I spend the up to $1400 to be Sender Score certified.

Why would this "SmartScreen" consider any messages from a personal domain, with no signatures containing hyperlinks or images, spam? I look at my test Hotmail account, and see the dozens of spam received in the INBOX every day. How is it that SmartScreen doesn't filter out that garbage? I'll tell you why, because the spammers themselves are probably Sender Score certified. Nice. They make millions a year, what's $400 to them?

I'm beginning to think that this Sender Score certified idea is a racket. "Hey, pal. Would be a shame if something happened to yous nice little domain, wouldn't it? You need protection - pony up!"

What a damn shame. I'm telling everyone I know to move to Yahoo or Gmail. I'm disgusted by Microsoft's IdiotScreen technology. BOOOOOOO!

Anonymous's picture

Problem goes back longer than last year....

The problems you are describing go back further than last year. More like 2 to 3 years ago.

Bell Canada operates an Internet service called Sympatico. A couple of years ago they teamed up with Microsoft and are doing some co-branding. The Sympatico email accounts are now hosted on a server that uses the Hotmail system. You can log into it through your browser and it looks exactly like Hotmail, however Sympatico is the logo they use of course. You can also set up your email client if you prefer using it. The SMTP server is called smtphm.sympatico.ca. (the "hm" is for Hotmail). I found out that if you send email to a Hotmail account through this SMTP server, your email will almost never arrive. This is kind of ridiculous when you think about it. I haven't tried it from the Webmail interface yet. Nevertheless, this is basically a complete stupidity. I kept sending emails to people and they never received them. I was also using a non "sympatico.ca" email address as the sender. Perhaps if I had used the email address it might have worked. I guess their stupid SmartScreen technology flagged my emails as spam. I then found out that Bell Canada was still using their former SMTP server smtp1.sympatico.ca, so I switched to that and now approximately half of the emails arrive in Hotmail accounts. Still not great of course.

The other stupidity with Hotmail is that you cannot send people most types of attachments (especially EXE files). The attachment arrives and is displayed, but it's greyed out and you cannot open or download it. You can't even open something as simple as JPG's much of the time.

I tell people to use Yahoo instead, because Yahoo accepts all attachments and the email almost always arrive. Their spam filter seems to work better! I've been told that even the Gmail spam filter works better than Hotmail.

You know, the bottom line is that Microsoft is a crappy software company and almost anything they touch or do has enormous problems. When Hotmail was stilled owned by the original founders it functioned much better. I used to have an account and it was a real pleasure to use. It was even possible to use a 3rd-party software to download emails into your email client. Since Microsoft took over it's become another crappy, bug-infested behemoth like their operating systems and other products.

Anonymous's picture

i have the same problem!

Thanks for the article, it's nice to know there are (many) other people out there having this issue. We have tried everything to fix this issue and it now seems there is no fix.

As a webmaster it looks like I have no option but to prevent anyone one with a hotmail address from joining our site and instead promote other free email services.

Anonymous's picture

Puzzling

Quote:
"I can send to Hotmail without a problem using Outlook 2003, but no cigar with Mozilla Thunderbird. "

What, Microsoft block email sent via a competitors product? Surely not! Why, that would make their competitors product look unreliable, so I can't see why they would want to do that.....

Anonymous's picture

I also having the same

I also having the same trouble and now have a policy of warning all hotmail user that my CMS will not accept them on hotmail accounts and that they should use gmail or yahoo. In some cases I have issued mail accounts to some of my users (critical) to ensure they get any email I send out.

Anonymous's picture

Nice to see that it wasnt' just me

I've been configuring our email server recently trying to get our emails to Hotmail accounts to work and also discovered that we can send a message using Outlook with no problems at all, but the identical message sent from Thunderbird or Eudora is silently eaten by the Hotmail mail server.

I too also noticed that Bell Sympatico uses Hotmail under the covers recently as I've been looking more closely at email headers in messages I received and discovered hotmail lurking in the headers of a message sent to me from a bell sympatico email account.

I've suggested this issue as a story to BBC's Click Online program and I recommend that anyone else that comes across this repeat it elsewhere prominently as well, people really need to be aware of this problem.

In the meantime I will do as this author has done and warn people away from it on our web page and provide links back to this and the "The Register" article that brought me here:
http://www.theregister.com/2007/05/01/hotmail_friendly_fire/

Anonymous's picture

Bell-Sympatico users suffering as well.

Sympatico users suffer from this as well since Bell-Sympatico "upgraded" its Email platform to hotmail/MSN. Now there are a whole variety of problems with disappearing Emails.

You might as well ban the "Sympatico.ca" domain as well since it it now hotmail.