Hotmail Doesn't Deliver Mail

Rant, not news. WYPIWYG.

Hotmail has a system for rejecting mail/spam, it's not perfect, and I don't expect it to be. I as a Hotmail user cannot check my spam, though, because Hotmail isn't 'marking' mail as spam - they just do not deliver those messages to me at all. So Hotmail incorrectly marks something as spam, flat out rejects it, and I have no clue.

I don't believe it is fair for Hotmail to conveniently "ignore the mailbox owner" when mail is intentionally blocked from getting to them. This hurts both ways.

When it's not spam and its sent to my Hotmail account, it's stuff I expect to get. Hotmail interrupts and rejects it as spam, but doesn't tell me. I am led to believe that a legit sender never sent that message. I look impatient, sender looks disorganized, Hotmail looks like a meddler. I'm upset.

Equal problem when I send an email to Hotmail, and Hotmail intentionally blocks that mail. Hotmail informs me (the sender) the mail was rejected, but the intended recipient never even knows I even bothered to try. Same problem as above - all frowns. I have tried emailing my own Hotmail account from gmail, from dentonlt.com, from another XXX.org.au, and from Hotmail back to Hotmail. It all gets blocked. I am -very- upset.

What about when Hotmail is where that recipient -wants- to receive their mail? What does the sender say? "Sorry, I can't email you, Hotmail is rejecting my mail and says I'm spamming you?" What part of "Dear wife, can we meet for lunch?" looks like spam?

Hotmail does its best to filter out junk/spam, just like every other mail service. Junk filters are never perfect, and I don't expect them to be. The spam folder saves the spam filter, though. I can go and clean the folder of 'not spam', or chuck back into that folder anything 'spam'. The system learns, doesn't block that next time, etc.

Funny enough, this looks like a non-issue with any provider but Hotmail, and it is very old news. Google "Hotmail Rejects Vodafone".

I once had a Hotmail account that I used a lot. I didn't know my mail wasn't arriving, though, didn't know Hotmail wasn't delivering messages that were actually legit. Along the way, I honestly wonder who had tried to send me mail that they dumped/blocked/rejected/neglected on my behalf?

Hotmail says that the way to solve this is to email Windows Live, request a fix, escalate to a manager, blah blah blah. You can guess how that has turned up so far. Thread below goes nowhere. They said (twice? I think just once) that they have contacted my mail administrator, and they haven't. Not cool. Intentionally neglectful.

Maybe they tried to email him at a Hotmail account. (Sorry, couldn't help it.)

Yes, Hotmail is free, but come on. Just because your service is free doesn't mean you can ignore the primary product - delivering mail. Google shows 805 million links for free email.

Insert foul language.

====

from Andrew
to XXX
date Tue, Jun 29, 2010 at 1:09 AM
subject RE: SRX1134082827ID - Sender Information for Hotmail Delivery

hide details 1:09 AM (10 hours ago)

To let you know, I have nor received anything at all re this, and I have
checked further up the line and neither have they

----------------------------------
XXX
Design & Web Director
XXX
XXX
XXX
----------------------------------

-----Original Message-----
From: XXX
Sent: Tuesday, 29 June 2010 11:00 AM
To: Microsoft Customer Support
Cc: XXX; XXX; XXX
Subject: RE: SRX1134082827ID - Sender Information for Hotmail Delivery

- Hide quoted text -
[ Andrew / Andrew: just FYI that this project is still
rolling ]

Hello now: Carlo, Marianna, Manny, Farley:

This is already getting out of hand. I imagine that whoever reads this
next will be another newcomer to the situation, and I am sorry that
you are picking up the unfinished work of others.

The short story:

This is basically a variation on "Hotmail does not accept any mail
from Vodafone.net".

I am sending mail to officers for/to/from a volunteer/nonprofit
organization at XXX. Those officers have asked me, in
person, to send XXX mail to those hotmail accounts.
XXX incoming mail is being rejected by hotmail, however.

I understand 500+ errors, spam controls/policies, the whitepapers
sent, etc. This is a volunteer/nonprofit org, however, so we cannot
afford a dedicated private server to make significant changes.

I am most surprised and disappointed that it is not possible for
officers who use hotmail to send messages to other officers who use
hotmail. I am increasingly vexed that my non-spamlike-mail is being
being identified as spam, completely blocked rather than filed as
spam, and offered solutions to make it look less spam-like.

Re the most recent message from Win Live: I have not received any
message from an individual named Marianna. I will appreciate that
being resent, yes, but I am first and foremost concerned with non-list
members: officers on hotmail sending mail to other officers on hotmail.

Since this problem started, I have set up -my own- hotmail account to
test the problem. I am upset that there is no obvious way to whitelist
mail from XXX directed to my own hotmail acocunt, and that I
flat out cannot receive my mail there.

Before suggesting I read more papers, or put you in contact with more
webmasters and administrators, please read the complete service
thread. I have already:

* used proper channels, filing a report with Win Live
* received multiple messages about escalation, solutions, etc.
* read the online docs for server admins
* read the enhancement papers (that have been sent more than once)
* searched for local solutions, and found that this is not a unique
problem to the XXX server.
* am still waiting to hear whether MSN Live has actually contacted
-the correct- server admin / ISP. I do not know who has been
contacted, so I assume Win Live has contacted the wrong person.
* have been told more than once that this has a reasonable resolution

I have -not-:
* been told that this has no solution at the -hotmail- end
* been clearly informed as to why XXX mail is being rejected.
Is it our senders? Is it our server settings? Is it our mail content?
* been told a solution that will work. I -have- been told to do things
that will make our mail look less spam like. Since our mail is not
treated as spam by the hotmail servers, however, I am uninterested.
Spam gets junk filed. Our mail gets flat our rejected.

May I suggest that some just whitelist our server so that we can all
move on.

If this is NOT going to be resolved, just tell me that so that I can
get on with our organization's business. These are volunteer hours and
this is not the best use of my time, our officers, or yours. I do not
have time or money to invest in changing server settings, software,
registrations, etc when this is a problem unique to hotmail.

Denton Thomas
XXX
National Secretary
XXX

Alt contact: denton@dentonlt.com

Quoting Microsoft Customer Support
:

> Hi Denton,
>
>
>
> This is Manny from the Windows Live Hotmail Domain Support team. Thank

> you for writing back.
>
>
>
> My colleague, Marianne, just replied to your issue and has listed
> troubleshooting steps that you can consider. Just to be sure, I will
> be highlighting the important steps that you can follow:
>
>
>
> -Clean up your lists. Remove those who do not want to receive the
> emails. Make the unsubscribe process more visible. Hotmail also has a
> sender complaint feedback loop program called the Junk Email Reporting

> Program (JMRP). Enrollment in this free program will benefit you as a
> sender as it will keep your email lists updated and populated with
> interested Windows Live Hotmail Customers. This program will help you
> to remove those Windows Live Hotmail Customers who do not want to
> receive emails from your company. If you are interested in joining
> this program, please visit
- Hide quoted text -
> http://support.msn.com/eform.aspx?productKey=edfsjmrpp&page=support_ho
> me
> _options_form_byemail&ct=eformts
>
> e_options_form_byemail&ct=eformts>
>
>
>
> For more detailed information about best practices delivering to Live
> Hotmail, please review the following white paper:
> http://download.microsoft.com/download/e/3/3/e3397e7c-17a6-497d-9693-7
> 8f
> 80be272fb/enhance_deliver.pd
>
> f80be272fb/enhance_deliver.pd>
>
>
>
> Please verify if you have received the reply of Marianne. If not, I
> will be more than happy to resend it to you.
>
>
>
> The troubleshooting steps in this email are recommendations only.
> Microsoft makes no guarantees that following these steps will
> guarantee deliverability to MSN, Windows Live Hotmail, or Live.com
> customers.
>
>
>
> Thank you.
>
>
>
> Manny
>
> Windows Live Hotmail Domain Support
>
>
> _____
>
>
>
> --- Original Message ---
> From : "XXX"
> Sent : Monday, June 28, 2010 11:56:27 AM UTC
> To : "Microsoft Customer Support"
> Subject : RE: SRX1134082827ID - Sender Information for Hotmail
> Delivery
>
> Hello, Farley/Carlo et al.
>
> Do you mind my asking who you have contacted? I had provided our
> server admin / ISP:
>
> XXX, (XXX; Australia)
> attn: Andrew XXX
> XXX
>
> Just want to be sure you're inquiring with the right person.
>
> Denton Thomas
>
>
>
> Quoting Microsoft Customer Support
> :
>
>> Hello Denton,
>>
>>
>>
>> My name is Farley from the Windows Live Hotmail Domain Support.
>>
>>
>>
>> We tried to contact your domain administrator and are still waiting
> for
>> a response. I'm following up with our request to get additional
>> information from them and once we get the information that we need,
>> we will look into your IP's deliverability issue immediately and
>> you'll receive an email from us.
>>
>>
>>
>> Warm Regards,
>>
>>
>>
>> Farley
>>
>> Windows Live Hotmail Domain Support
>>
>>
>> _____
>>
>>
>>
>> --- Original Message ---
>> From : "XXX"
>> Sent : Sunday, June 27, 2010 6:41:22 AM UTC
>> To : "Microsoft Customer Support"
>> Cc : "XXX" , "denton@dentonlt.com" Subject : RE:
>> SRX1134082827ID - Sender Information for Hotmail
> Delivery
>>
>> Hello, Carlo.
>>
>> Thanks for the update. Up front, I'll let you know that I am
>> pessimistic! Too much bad press online, I am afraid. Unfortunately,
>> it is a timely/important issue for us.
>>
>> A relatively small percentage of our organization is online right
>> now, only ~ 20 officers of 400 active members nationally. As we
>> activate member services/access online, I expect the problem will
>> expand. The current 2-3 people I can persuade ... but 30-40
>> people/accounts I can't, and I can't predict how big we will be in 5
>> years.
>>
>> I've looked through the MS spec sheets, and I understand there are
>> methods to register mail servers, provide identification, etc. In any

>> case where XXX is required to hire significant time changing server

>> software or settings, however, it probably won't be a valid solution
>> at our end. We're financially quite small, and don't have resources
>> for it.
>>
>> Despite any worries I have, I do look forward to hearing from you in
>> the week ahead. Let me know if I can be of any more assistance.
>>
>> Denton Thomas
>> XXX
>> National Secretary
>> XXX
>> Alt contact: denton@dentonlt.com
>>
>> Quoting Microsoft Customer Support
>> :
>>
>>> Hello Denton,
>>>
>>>
>>>
>>> This is Carlo with Windows Live Hotmail Domain Support.
>>>
>>>
>>>
>>> Our goal in Windows Live Mail is to make sure that every wanted
>> message
>>> sent to Hotmail customers arrive in their inbox, and I know how
>>> frustrating it is when this does not happen. It appears that your
>> domain
>>> is being affected by one of our anti-spam or bulk message filters.
>>> As
>> a
>>> part of the Sender Escalations Team, I work with directly with
>> senders,
>>> domains, other ISPs to resolve mail delivery failures.
>>>
>>>
>>>
>>> While I cannot resolve this for you immediately, I will attempt to
>>> contact the administrator of "XXX". It may take a few days
> to
>>> resolve this issue and for your sent mail to arrive as you intended.
>>>
>>>
>>>
>>> For more detailed information about best practices delivering to
>>> Live Hotmail, please review the following white paper:
>>>
>>
> http://download.microsoft.com/download/e/3/3/e3397e7c-17a6-497d-9693-7
> 8f
>>> 80be272fb/enhance_deliver.pdf
>>>
>>
> > 78
>>> f80be272fb/enhance_deliver.pdf>
>>>
>>>
>>>
>>> Thank you and have a great day.
>>>
>>>
>>>
>>> Best regards,
>>>
>>>
>>>
>>> Carlo
>>>
>>> Windows Live Hotmail Domain Support
>>>
>>>
>>> _____
>>>
>>>
>>>
>>> --- Original Message ---
>>> From : XXX
>>> Sent : Friday, June 25, 2010 12:11:33 PM UTC
>>> To : 7cc61df2-a4df-477a-8f5c-92f4549b368e
>>> Subject : Sender Information for Hotmail Delivery
>>>
>>> Service:
>>> Sender Information for Hotmail Delivery
>>>
>>> What type of problem do you have?
>>> Primary company contact name
>>> Denton Thomas
>>>
>>> Primary company contact email address
>>> XXX
>>>
>>> What domain are you sending from?
>>> XXX.org.au
>>>
>>> How would you describe your company or yourself?
>>> Customer of an ISP other than Windows Live Hotmail [Customer of
>>> an ISP other than Windows Live Hotmail]
>>>
>>> What are the IP addresses of your outbound mail server (as seen by
> the
>>> receiving mail server)?
>>> Frankly, I'm not the server admin! Best guesses from headers:
>>> 202.125.33.7; 202.125.33.80; 114.78.167.38
>>>
>>> Is your server dedicated or shared?
>>> Shared [Shared]
>>>
>>> Be specific when describing your problem. The details that you
> include
>>> enable us to promptly send you the most likely solution to your
> issue.
>>> The XXX
>>> is
>> a
>>> non-profit organization in Australia. Members/officers are primarily

>>> professional XXX. Personnel communicate via
>> emails,
>>> some aliased/redirected through XXX
>>> (XXX, for example, redirects mail to a personal
>>> account). This provides
>> stable
>>> addresses despite regular changes of personnel. Currently,
> MSN/Hotmail
>>> accounts are irregularly rejecting emails which originate from the
>> XXX
>>> site - XXX. XXX, for example,
>> reroutes
>>> to an individual officer's hotmail account as below. That account
>>> rejects XXX mail, however (550). Non-officer members pay
>>> for
>> a
>>> membership which includes State and National email lists. These are
>>> typical, Mailman-managed lists that include opt in/out details on
>> every
>>> email.
>>>
>>> Copy and paste any error messages:
>>> Sample of typical 550 bounce from hotmail:
>>> ====
>>> Hi. This is the qmail-send program at specialmail.hostname.net.au.
>>> I'm afraid I wasn't able to deliver your message to the following
>>> addresses. This is a permanent error; I've given up. Sorry it didn't

>>> work out.
>>>
>>> XXX:
>>> Connected to 65.55.37.88 but sender was rejected.
>>> Remote host said: 550 SC-001 Mail rejected by Windows Live Hotmail
> for
>>> policy reasons. Reasons for rejection may be related to content with

>>> spam-like characteristics or IP/domain reputation problems. If you
> are
>>> not an email/network admin please contact your E-mail/Internet
> Service
>>> Provider for help. Email/network admins, please visit
>>> http://postmaster.live.com for email delivery information and
>>> support
>>>
>>> --- Below this line is a copy of the message.
>>>
>>> Return-Path: XXX
>>> Received: (qmail 13542 invoked from network); 25 Jun 2010 11:19:25
>> -0000
>>> Received: from unknown (HELO mail3.sslaccess.com) (202.125.33.7) by
>>> specialmail.sslaccess.com with SMTP; 25 Jun 2010 11:19:25 -0000
>>> Received: (qmail 2553 invoked from network); 25 Jun 2010 11:33:41
>> -0000
>>> Received: from unknown (HELO mx3.sslaccess.com) (202.125.33.80) by
>>> titan.ozservers.com.au with SMTP; 25 Jun 2010 11:33:41 -0000
>>> Received: (qmail 29934 invoked by uid 110); 25 Jun 2010 21:33:47
> +1000
>>> Delivered-To: 613-XXX
>>> Received: (qmail 29920 invoked by uid 33); 25 Jun 2010 21:33:47
>>> +1000
>>> Received: from d114-78-167-38.meb801.vic.optusnet.com.au
>>> (d114-78-167-38.meb801.vic.optusnet.com.au [114.78.167.38]) by
>>> XXX (Horde MIME library) with HTTP; Fri, 25
> Jun
>>> 2010
>>> 21:33:47 +1000
>>> Message-ID: 20100625213347.g7jnztx8qo80oggc@XXX
>>> Date: Fri, 25 Jun 2010 21:33:47 +1000
>>> From: XXX
>>> Cc: XXX
>>> Subject: XXX - rejection test
>>>
>>> Amy -
>>>
>>> Some mail from XXX is getting rejected by your hotmail
>>> account. Specifically, if I send from dentonlt.com -
>>> XXX.
>>>
>>> In hotmail, can you whitelist the XXX email
>> address?
>>>
>>> Also, do you mind checking your spam filter to see if any
> XXX
>>> email has gone there? If so, it would help if you mark any of it as
>>> 'not spam.'
>>>
>>> Sorry for the problems - can't do anything about it from my end :/
>>>
>>> DLT
>>>
>>> What ISP are you using?
>>> XXX hosted by XXX (XXX);
>>> organizational users have private accounts that send/receive mail
>>> through XXX aliases/redirects
>>>
>>> What OS are you using?
>>> Server: Linux/apache; Email clients: cross-platform
>>> (Mac/PC/Linux)
>>>
>>> What mail transport software are you using?
>>> GNU mail (?)
>>>
>>> What mailing list management software are you using?
>>> GNU Mailman; Plesk/Groups (not managed as lists)
>>>
>>> How are bounce messages (non-delivery reports) handled by your
> system?
>>> All bounces relayed to list administrator for handling. Mailman
>> uses
>>> default config/settings for bounce handling, excepting bounce
>> threshold
>>> is lowered (3.0).
>>>
>>> How frequent are your mailings?
>>> ~ 1 per 30 days
>>>
>>> What are the volume of your mailings?
>>> 150 recipients
>>>
>>> What are some of the accounts on Microsoft's systems that you are
>>> attempting to send mail to?
>>> XXX@hotmail.com; XXX@hotmail.com;
> XXX@hotmail.com;
>>> XXX@hotmail.com; XXX@hotmail.com
>>>
>>> Do your SMTP logs show any failed transactions when attempting to
> send
>>> to addresses at MSN, Windows Live Hotmail or other MSN Services? If
>> so,
>>> include those entries here.
>>> XXX server administration outsourced/hired by our
>>> organization (from XXX). Unfortunately, that means
>> officers
>>> (me!) do not have access to SMTP logs for our domain. This also
>>> keeps officers (me) from personally checking telnet/traceroute from
>>> our
> mail
>>> server - I have no SSH access. Our IP is static, however, I have no
>>> information regarding whether our mail servers/services are
> registered
>>> with any of the services below: Return Path, Sender Score,
>>> SPF/Sender ID, Junk Mail, Smart Network Data.
>>>
>>> Can you telnet to port25 of mx1.hotmail.com from your mail
server(s)?
>>> No [No]
>>>
>>> Can you traceroute to 216.32.183.201 from your mail server(s)?
>>> No [No]
>>>
>>> Please copy/paste samples of a few of the messages you're sending -
>>> including full headers - as seen by your recipients.
>>> Typical officer-to-officer message. Gmail to XXX to
>> hotmail.
>>> Hotmail rejects message (550 reply above).
>>> =====
>>> Received: (qmail 29920 invoked by uid 33); 25 Jun 2010 21:33:47
>>> +1000
>>> Received: from d114-78-167-38.meb801.vic.optusnet.com.au
>>> (d114-78-167-38.meb801.vic.optusnet.com.au [114.78.167.38]) by
>>> XXX (Horde MIME library) with HTTP; Fri, 25 Jun
>> 2010
>>> 21:33:47 +1000
>>> Message-ID: 20100625213347.g7jnztx8qo80oggc@XXX
>>> Date: Fri, 25 Jun 2010 21:33:47 +1000
>>> From: XXX
>>> To: XXX
>>> Cc: XXX
>>> Subject: XXX - rejection test
>>> MIME-Version: 1.0
>>> Content-Type: text/plain;
>>> charset=ISO-8859-1;
>>> DelSp=Yes;
>>> format=flowed
>>> Content-Disposition: inline
>>> Content-Transfer-Encoding: 7bit
>>> User-Agent: Internet Messaging Program (IMP) H3 (4.1.6)
>>>
>>> Amy -
>>>
>>> Some mail from XXX is getting rejected by your hotmail
>>> account. Specifically, if I send from dentonlt.com -
>>> XXX.
>>>
>>> In hotmail, can you whitelist the XXX email
>> address?
>>>
>>> Also, do you mind checking your spam filter to see if any
> XXX
>>> email has gone there? If so, it would help if you mark any of it as
>>> 'not spam.'
>>>
>>> Sorry for the problems - can't do anything about it from my end :/
>>>
>>> DLT
>>>
>>> In what manner(s) are recipients added to your mailing list(s)?
>>> Recipients are fee-paying organization members; manually added in

>>> Mailman or CiviCRM interfaces.
>>>
>>> Provide the URL of your web site.
>>> XXX
>>>
>>> Provide the URL of your Privacy Policy.
>>> http://XXX
>>>
>>> Provide the URL at which users opt-in to receive your mailings.
>>> n/a - list/alias additions are made/managed by administrator only
>>>
>>> Provide the URL at which users may choose to permanently unsubscribe

>>> from your mailing list.
>>> alias changes are internally handled by webmaster
>>> (Plesk/Parallels interface); mailman lists are handled at
>>> http://XXX
>>>
>>> Are you currently a Return Path client?
>>> No [No]
>>>
>>> Are you Sender Score Certified?
>>> No [No]
>>>
>>> Do you publish Sender Policy Framework (SPF)/Sender ID records for
>> your
>>> IP?
>>> No [No]
>>>
>>> Do you use separate IPs for your transactional vs.
>>> promotional/subscription marketing communications?
>>> No [No]
>>>
>>> Are you in the Junk Mail Reporting Partner Program?
>>> No [No]
>>>
>>> Do you use Smart Network Data Services?
>>> No [No]
>>>
>>>
>>>
>>> Which operating system are you using?: Mozilla/5.0 (X11; U; Linux
>> i686;
>>> en-US; rv:1.9.2.3) Gecko/20100401 Firefox/3.6.3
>>>
>>> Which browser are you using: Firefox3.6.3
>>>
>>> Location: en-us - English (United States)
>>>
>>> Type of Support: E-mail Support