Are Hotmail cutting their own throat

http://www.iis-aid.com/articles/iis_aid_news/are_hotmail_cut ting_their_own_throat


Are Hotmail cutting their own throat



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.


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.
How do I fare with other free email providers
This explanation did not sit right with me as I knew I had a
reasonably tight email setup, plus the fact that I still get half a
dozen or so emails a week in my Hotmail account that are obviously
spam which go directly to my inbox. As a test I decided I would sign
up with several other free email service providers and see what
happened to my email when sending to those accounts. I did a quick
search on the most popular free email services in use today, and found
this article. I went ahead and signed up an account with each of the
following providers leaving the spam filtering in each of them to the
default settings, and sent each of them an identical email;

* Gmail
* Inbox
* FastMail
* Yahoo
* AOL Mail
* HotPOP
* Groowy Email
* MSN Hotmail
* BigString
* My Way Mail

How did it turn out? Well, after testing all ten accounts I can say
that Hotmail was the only provider that did not deliver my mail. Not
only that, but my email went straight to the inbox with 8 of those
providers. The mail I sent to my Inbox account arrived, but was
directed to the spam folder. I raised three support tickets with Inbox
support asking why my mail was sent to the spam folder, but the only
reply I ever got was to loosen my spam filtering or add my address to
the whitelist. I tried to explaining that wasn't the point, but could
never get my message through. I took some solace in the fact that mail
sent from my Googlemail and Yahoo accounts to my Inbox account were
also sent to the spam folder.


UPDATE: Email clients play a role too
While reading back through this article I noticed that it was totally
server centric, with no consideration of what an individual email
client might be doing to effect an emails deliverability to Hotmail.
Email clients are responsible for adding header information which is
widely used for aiding in anti spam purposes.
I started playing around with clients rather than concentrating on
server setup, and I've had some interesting results. I can send to
Hotmail without a problem using Outlook 2003, but no cigar with
Mozilla Thunderbird. I haven't tested other email clients yet, but I
think that this suggests that the headers the email clients add to an
email also play a crucial role in determining if the mail gets through
or not. This is BAD news because as a system admin there is generally
very little you can do about this. I'll be interested to continue
testing, especially with the user-agent and x-mailer headers.
Conclusion
This one should not be a hard one to come to. If people are not able
to be confident that mail sent to Hotmail will get there, then why use
their services? Especially when there are so many other players in the
field. I have now configured rules for this website that ban the use
of Hotmail addresses during signup, and have configured my email
server to send a message to any of my users sending to a Hotmail
account informing them that their email is unlikely to get through. I
realise that me banning Hotmail is not going to make any difference,
but get 1000, then 10,000 the 100,000 other webmasters just like me
doing the same thing and you really have to ask yourself. Are Hotmail
cutting their own throat?
Vote Result

Bookmark/Search this post with:
| | | | | |
IIS-Aid News | My Word | email this page | 3397 reads
Submitted by Dominic Ryan on Thu, 2007-03-22 12:25.



Same problem...
Anonymous | Fri, 2007-03-30 18:36
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.

reply | email this page

Same Problem with my accounts also
Anonymous | Wed, 2007-04-04 13:30
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.

reply | email this page

Yeah, I think before too
Brashquido | Wed, 2007-04-04 17:17
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.

reply | email this page

Absurd
Anonymous | Thu, 2007-04-26 03:30
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!

reply | email this page

Problem goes back longer than last year....
Anonymous | Thu, 2007-04-26 04:56
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 name@sympatico.ca 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.

reply | email this page

i have the same problem!
Anonymous | Thu, 2007-04-26 12:25
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.

reply | email this page

Puzzling
Anonymous | Tue, 2007-05-01 08:21
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.....

reply | email this page

I also having the same
Anonymous | Tue, 2007-05-01 09:51
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.

reply | email this page

Nice to see that it wasnt' just me
Anonymous | Tue, 2007-05-01 16:36
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/

reply | email this page

Bell-Sympatico users suffering as well.
Anonymous | Wed, 2007-05-02 15:12
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.

reply | email this page

Sign the Petition to remove SmartScreen technology
Anonymous | Mon, 2007-05-07 04:59
Remove SmartScreen technology from Hotmail & Windows Live Mail.
Sign the petition right here:
http://www.petitiononline.com/notsmart/

reply | email this page

Try to fight with hotmail support
Anonymous | Tue, 2007-05-08 02:49
I have had same issue with hotmail. After weeks of negotiations with
the hotmail technical support, problem has been solved.
But, in any case, I do not recommend to "communicate" with them.
Always inform users about possible disruptions in sending mail from
your servers to hotmail accounts (through hotmail faults).

reply | email this page

So glad I found this article
Anonymous | Thu, 2007-05-10 04:17
I'm no sysadmin but I fill the shoes at our office and at home. I had
come to the conclusion that it wasn't my relative lack of knowledge
but actually hotmail blocking my messages. Now all is confirmed.
Outlook & Outlook expr, both work to hotmail, but no-go with T-bird. I
finally dumped that waste of money ISP Sympatico also. Went with
Velcom and a static IP for $20 bucks less a month than Sympatico. Symp
want (I think) around $90 cdn a month for a static IP!!!! Down with
the big boys!

reply | email this page

Careful With Accusations
Anonymous | Thu, 2007-05-10 22:15
Sender Score Certified is an independent 3rd part that maintains the
whitelist that is used by 100's of other ISP's. I would not be
surprised if you start seeing the other big boys behaving like this as
well.

reply | email this page

Sender Score Certified might
Brashquido | Fri, 2007-05-11 23:28
Sender Score Certified might be an independent 3rd party, but
regardless of how it is put forward it still spells trouble for small/
medium business with their own messaging infrastructure who cannot
afford to pay upwards of $1000USD a year to maintain membership. I'd
also be hesitant to use such as system as it bypasses your SPAM
filters, especially when commercial entities can still send unlimited
and unsolicited emails for $20,000 a year. Just sounds like it is a
lot more about making money than stopping spam, especially with
comments such as this in their FAQ;
Quote:
If you are sending legitimate email with a negligible complaint rate
AND you want to ensure your email isn't blocked or put into the bulk
folder, Sender Score Certified is for you.

Define legitimate email, and what is a negligible complaint rate? This
description is a little bit too loose I think, especially when Return
Path stand to make a lot of money by letting their certified customers
send more email.

reply | email this page

Lost files and Folders
Anonymous | Thu, 2007-05-17 12:58
Hi Everyone,
Can you pls help. I a have a Hotmail account but had not accesed it
for some time. Last night I wanted to have a look at my previously
save folders and I was asked to re-activate the account, which I did
but WHERE is my important folders and files gone? Can I ever recover
these?
Pls help.
Thanks
Korehan

reply | email this page

That's happened to me a few
Brashquido | Thu, 2007-05-17 19:03
That's happened to me a few times in the 8 years I've hat my hotmail
account Korehan, and another reason not to use Hotmail for important
communications. Unfortunately I would say that all your data is gone.
You could try contacting Hotmail support, but I don't like your
chances of being able to get anything back from one of their free
accounts.

reply | email this page
Post new comment

Subject:


Comment: *

* You may link to webpages through the weblinks registry
* Lines and paragraphs break automatically.
* Images can be added to this post.
* You can use BBCode tags in the text, URLs will be automatically
converted to links
* Use the special tag [adsense:format:group:channel] or
[adsense:flexiblock:location] to display Google AdSense Ads.
More information about formatting options

Captcha Validation: *

Please type in the letters/numbers that are shown in the image above.

Preview comment Post comment