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

I can send now

After 3 months sending emails to microsoft's support, they finally removed my IP from their black list.
I did all the steps suggested in this pdf http://download.microsoft.com/download/e/3/3/e3397e7c-17a6-497d-9693-78f80be272fb/enhance_deliver.pdf
except pay for third part white list, and they finally answered me with this:

"I am pleased to inform you that we have taken steps to implement a temporary mitigation to your mail delivery problem. The mitigation will take 24-48 hours to fully reflect in our system.

During the mitigation period your emails should not experience any issues arriving in Hotmail customer's inboxes. This period will also give our filters sufficient time to learn enough about your mailing practices that after the mitigation expires your mails shouldn't any issues with arriving in our Hotmail customer's inboxes. Hotmail has created group of programs that should benefit your mailings during this time. To help avoid future issues I would strongly suggest enrolling-in or implementing these if you have not already. "

So, never quit!

Anonymous's picture

Why doesn't Microsoft take this problem seriously?

I have several websites at different hosting companies. For the last two years I have gotten complaints from new users signing up who says they never receive verification e-mail (I use that to verify that the e-mail address is valid) and thus can't login for the first time. Everyone who has problems was using hotmail.
I haven't spent much time trying to get it working since the majority of users still have other e-mail providers.
But recently I set up two sites at the same hosting, therefore using the same mail server although different domains. One of them works without problems, even hotmail users recive notifications by mail.
But on the other mails disappear into the Hotmail Black Hole. No bouncing, no errors. Irony - all my websites run on Microsoft software...

I found this story and everything made sense. What strikes me is that these problems were reported to Microsoft early 2007 - and still almost a year later they have done NOTHING to take care of it?
I think that to few end users have been informed. To few website owners have started blocking hotmail users from signing up. Probably because MS help the bigger ones out and ignores the small.

Hosting companies have more or less given up since Microsoft only provide useless support as reported by many people on these forums. Even when supplied with sufficient evidence the support staff sends back "have you looked in the Junk folder?"-kind of replies.

What if all affected by this set up auto-replies "Unfortunately we cannot accept e-mail from hotmail.com-domain until Microsoft accepts the e-mails we send out. Please contact Microsoft support. If they can't help you, here is a list of other great mail services that are free as well:"

Anonymous's picture

Why even honour them with

Why even honour them with specific mention of their name.
it'll only boost up their search engine results and make that retarded #opps#s look important.

back in the days, whenever there was a 'well known' problem with one of the crappy free mailers we just put them into the enemy list in the signup thing going 'we don't accept e-mail addresses from this country/company for technical reasons' or something like that, you don't specifically mention 'hotmail' on your sites, that will only give them a hard one.

as for the rest of it, we can pull m$ tricks as well but having sites going 'this site won't display unless you upgrade to a real operating system with a real browser' doesn't exactly help the cashflow process :P

although you could try to get microsoft to pay $1400 to be 'approved' to 'fix' the problems with their browsers/e-mail users/clients/etc :P

clearly these people still don't have any understanding about the concept 'internet' which includes that i allow you to transfer your data over my network and you allow me to transfer my data over yours, also on higher levels such as e-mail exchange.

oh well, in the end, most people using m$ crap are low-budget customers anyway, we don't really miss out on a lot of money if we would just block them all artificially (ip fingerprinting or useragent or mailheaders wise).

but #opps# it, they're a has-been anyway.

Anonymous's picture

Sending POP mail using hotmail

I collect all my POP3 mail using Windows Live Mail. Two of the sources do not allow sending so I want to set Hotmail as the sending server.

Is this possible? What are the encantations needed? Thanks

Anonymous's picture

Want to get your rivals website banned?

Here is the most ludicrous thing about Hotmail.

Set up a new Hotmail account, import about 100 hotmail addresses into the contact list and then send a message to all of them using BCC

In the message put your rival websites address. The idiot Hotmail program will then pick up the URL and do a reverse ip check and ban the ip address.

How do I know this? Well, I was stupid enough to send an email to all my contacts informing them that our domain name had changed. Hotmail decided I was spamming and banned the new domain's server ip address.

To this day I still can't send an email from the server to any hotmail address. They just vanish.

So if you really want to get rid of all your web rivals just do the same thing. If enough people do it then maybe Hotmail will wake up and realize how stupid it is to ban a site based on a single URL in an email sent to multiple users. (I could understand this if I sent it to like 2 or 3 thousand, but just a hundred users? Wake up Hotmail)

Anonymous's picture

No hotmail is allowed

I am going to prevent users to sign up with hotmail account at my site, and I will force existing members to change their email address

Anonymous's picture

Ban the Hotmail

In my opinion - Microsoft cashing in and will end up loosing out end of day

i have many servers, some work fine some get blackholed

Keith

Anonymous's picture

Stupid workaround

I've been plagued with the same issue since relocating to a new dedicated hosting provider. The company is reputable, more so than the last, and RDNS is setup. SPF isn't configured, but wasn't before either. Nothing has changed except the IP, which was not black listed, yet mails vanished into the ether. Hotmail happily accepts the email with a 250 return code but decides not to actually deliver it.

A simple Perl script is used to email users on signup, and also for password retrieval. Troubleshooting from my home DSL account showed the problem not to be with the IP, but the format of the email. Send the exact same text through a simple text email and it works, sending it via telnet (trying to put in all the correct "Reply-To" and "X-Mailer" headers) did not work.

While playing around I found out two things made the mail suddenly work.

Firstly, send it to more than one recipient. Whilst I think this makes it look more like spam, Hotmail likes it. I have the sendmail "To:" line have the user's email address and also the mail-out accounts address.

Secondly, don't make the sender's name look pretty. No "From: Firstname Lastname ", just "From: ". Again I think it makes the email more spam-like, but both of these were necessary to make the emails work.

For reference the sendmail mail commands look like:

To: <user@hotmail.com>, <my-mailer@domain.com>
From: <my-mailer@domain.com>
Reply-To:
X-Mailer: My.TAG
Subject: Welcome to domain.com!

I've stopped new users signing up with hotmail accounts, but at least this precarious workaround lets existing hotmail users manage their accounts.

HTH

Anonymous's picture

Hotmail and Sympatico.ca

No, don't block Sympatico users as well!
I have a Hotmail and a Sympatico account and have the same problem with Hotmail - however, the same person who didn't receive my Hotmail messages, received the message when I sent it through Sympatico!
So, although these two email services are in kahoots, so to speak, the problem seems to be soley with Hotmail, not with Sympatico.
G.R.

Anonymous's picture

Re MSN HOT MAIL ACCOUNTS

I was so disappointed I have had the same MSN account & Password for years.Allof a suden nothing.I had several pages of e-mails were very valuable to me as I had cancer & they were sentimental & never cancelled them out & a lot of others also I lost all my contacts & everything.I think for a company to do such a horrible thing to people shows us what they are made of without letting us no they were going to do it & somehow we could have saved them
I AM WITH EVERYONE ELSE & IT SHOULD BE TAKEN TO FACE BOOK & EVERYONE SIGN IT THERE THEN MAYBE WE MIGHT GET SOMEWHERE.I AM NOT REAL GOOD ON THE COMPUTER SO MAKES IT HARD TO DO MOST THINGS.I HAVE HEARD SOME PEOPLE HAVE GONE TO GMAIL & LIKE IT MAYBE WE CAN FIND SOMEONE OUT THERE WHO WANTS EVERYONE & LEAVE THE ONES PLAYING WITH OUR LIVES TO DIE OUT