From: GEST HM Inbox []
To: []
Sent: Wednesday, September 20, 2006 95:37 AM
Subject: RE: Email Delivery Problem Questionnaire SRX060919607709


We have identified that messages from your IP are being filtered based on the recommendations of the SmartScreen filter. SmartScreen is the spam filtering technology developed and operated by Microsoft. SmartScreen is built around the technology of machine learning. SmartScreen’s filters are trained to recognize what is spam and what isn’t spam. In short, we filter incoming emails that look like spam. I am not able to go into any specific details about what these filters specifically entail, as this would render them useless.

However, we also base our spam rating on the reputation of the sender. One way to positively impact the reputation of your IP is to obtain SPF/Sender ID records. This technology allows SmartScreen to better track emails from your IP, weeding out spoofed messages. You can find additional information on creating SPF records at

Please confirm that your emails comply with MSN Hotmail’s technical standards. This information can be found at:

It will also be helpful to send example emails to from your MTA so that we can examine the types of emails that you send. This will help me in our investigation. When you do this please send me the subject lines of emails you have sent. Please make sure that these emails are functionally similar to the types of emails that originate from your system, as any deviation from this may hinder our ability to investigate your problem. Do not use the word, “Test” or anything that would change the email from the original message that was initially sent to Hotmail Customers.

I hope that the information that I have provided to you has been helpful. You may also be able to find additional information on common delivery questions at the Hotmail Postmaster Site found at: I would like to highlight some key areas which I believe are appropriate to your company.

Hotmail has created the Smart Network Data Services program. This is a service that helps legitimate email senders work with their customers and partners to reduce spam originating from their IP. This program allows a sender to monitor the ‘health’ of their IPs.

I would also strongly recommend that you Authenticate your outbound email via Sender ID and publish your SPF records for your outbound email IPs and register with Sender ID. You can find additional information at or you may email for support. Please note that technical standards (RFC 4408) discourage use of "ptr" for performance and reliability reasons.

Monitor user complaints. Hotmail also has a sender complaint feedback loop program Junk Email Reporting Program (JMRP). Enrollment in this, free of charge, program will benefit you as a sender as it will keep your e-mail lists updated and populated with interested MSN Hotmail Customers. Participation in this program will remove those MSN Hotmail Customers who do not want to receive e-mails from your company. If you are interested in joining this program please email

While using the SNDS tool, enrollment in the JMRP or having your IPs registered with Sender ID will not allow emails from your mail servers to bypass our filters, these are in place to help legitimate companies deliver their emails to Hotmail Customers.

SenderScore Certified Mail Program. Many legitimate mailers and marketers have qualified and joined this “white listing” program to improve mail deliverability and decrease email from being filtered to the Junk E-mail Folder. Sender Score is a third party program, administered by Return Path. Sender Score ( is the only White Listing service to which we subscribe.

The troubleshooting steps in this email are recommendations only. Microsoft makes no guarantees that following these steps will guarantee deliverability to MSN, Hotmail, or customers.

Thank you,
MSN Hotmail Domain Support

From: []
Sent: Tuesday, September 19, 2006 3:31 PM
To: Hotmail Unblocking Requests []
Subject: Email Delivery Problem Questionnaire

dear hotmail staff

I am the webmaster of a small picture based community platform called
we run this website as a free service for all people still in love with polaroid pictures.
the website is purely NON-commercial.

lately I get more and more complaints from hotmail users that I dont answer their emails and that they dont receive the automated notification emails (which they can decide to wanna receive in case of a comment being made to one of their images - or in case of a "guestbookmessage")

according to my mailserver logs these mails, as well the ones sent out by me (webmeí as well as the automated notifiaction mails (sent out from are sent out and accepted by the hotmail server.

since our users kept complaining and said they dont even find our mails (sent from in their junkmail folder - I decided to try myself and created an hotmail account (
and I saw that it is indeed true.
I sent a testmail from my normal email client from to, but the mail never showed up in my hotmail inbox - and also didnt bounce back to my sending account.
I generated a couple of "new picture comment" and "new guestbook message" notification mails (which are sent out by our webserver from the address - but only the "guestbook notifications" made it to my hotmail inbox.
the "picturecomment notifications" just were lost.
they didnt bounce back - just vanished.
this was basically the same what I heard from my users who run a hotmail account.
the strange thing is that "new picturecomment" and "new guestbook entry" notification mails are sent from the SAME server, from the SAME sender address and even have very similar subject lines.
so I cant really understand why the ones get delivered while the others just vanish.
and wouldnt it be somehow nice to inform the sender if a message is not deliverd to the receiver?
I think this is really hard...

please help me and tell me what I can do so that also hotmail users can user our website and get the emails they wanna get
and above all can receive the mails I - the webmaster of the site - am sending to them.
it is very unpleasant for me to know that some people dont receive the answers I'm sending in reply to their questions!

please tell me why some of the mails sent from our servers are delivered to hotmail and some are not.
and please tell me what I can do to change this unsatisfying situation.

below are the answers to your questions from

kind regards


ps: attached you find one "personal" email that didnt get delivered to a hotmail user and samples of the "automatic" notification mails that don't (the picture comment) and that do (the guestbook notification) get delivered.


1. What are the IP addresses of your outbound mail servers (as seen by the receiving server)? ( (

2. Is your server a dedicated or shared server?
a dedicated server

3. What ISP, operating system, mail transport software, and/or mailing list management software are you using?
root server at hetzner ag, germany (, linux, Postfix

4. How are "bounce messages" (non-delivery notices) handled by your system?
bounce back to sender - which is me in case of the relevant emails

5. How frequent are your mailings? What are the volumes of these mailings?
on the one hand I'm having problems with some messages from me ( not being delivered to hotmail users
on the other hand some of the automatically generated notification messages sent from ( not being delivered mailings from the webmeister@ account vary in frequency (1-20 per day)
the automatic mailings from schlexi@ depend on the number of these events that trigger them (guestbookmessages and picturecomments) - ranging from one every few weeks to 20 per day depending on the "popularity" of the respective user.

6. What are some of the accounts on Microsoft's systems that you are attempting to send to?
(original mail of course included the real addresses)

7. Do your SMTP logs show any failed transactions when attempting to send to addresses at MSN, MSN Hotmail or other MSN Services? If so, please include them inline in your response.
no error messages at all in mailserver log.
messages are accepted for delivery by hotmail.
Sep 19 23:55:19 www postfix/smtp[18462]: EC2472253C: to=,[], delay=2, status=sent (250 <> Queued mail for delivery)

8. Can you telnet to port 25 of from your mail server(s)?
yes, no problem

9. Can you traceroute to from your mail server(s)?
yes, no problem
traceroute to (, 30 hops max, 40 byte packets
1 ( 0.247 ms 0.193 ms 0.216 ms
2 ( 0.995 ms 0.813 ms 0.277 ms
3 ( 0.889 ms 0.586 ms 0.641 ms
4 ( 0.978 ms 0.664 ms 0.663 ms
5 ( 97.553 ms 97.471 ms 97.384 ms
6 ( 94.684 ms 94.176 ms 94.309 ms
7 ( 94.549 ms 94.512 ms 94.369 ms
8 ( 171.994 ms 171.909 ms 172.030 ms
9 ( 174.697 ms 174.412 ms 174.515 ms
10 ( 174.674 ms 174.396 ms 174.550 ms

10. Please include samples of a few of the messages you are sending, with complete headers (as seen by your recipients.)
see attachement

11. In what manner(s) are recipients added to your mailing list(s)?
we have no mailing list
the "automatic" notification mails (on new picture comment or guestbook message) sent to the users of our website can be turned on/off by the users if they want.

12. Provide the URL of your web site.

13. Provide the URL of your Privacy Policy.

14. Provide the URL at which users opt-in to receive your mailings.
unfortunately I can not send you this url, because the page with the checkbox users have to check so they receive these confirmation mails can only be accessed by logged in members of our community.

15. Provide the URL at which users may choose to permanently unsubscribe from your mailing list.
see 14.

16. Are you currently a Return Path client? Are you Sender Score Certified?

17. Do you publish Sender Policy Framework (SPF)/Sender ID records for your IP?

18. Do you use separate IPs for your transactional vs. promotional/subscription marketing communications?

19. Are you in the Junk Mail Reporting Partner Program?

20. Do you use Smart Network Data Services?