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I have problems sending emails from my server to hotmail. I used mxtoolbox.com and reported no problems on records or blacklists.

Also, emails go successfully to gmail...

This is my mail.log on sending email.

To hotmail:

Sep  4 01:13:50 NewWeb postfix/smtp[2860]: 4CC787FDE1: to=<xxxx@hotmail.it>, relay=mx2.hotmail.com[65.55.92.152]:25, delay=39, delays=38/0.01/0.4/0.76, dsn=2.0.0, status=sent (250  <20130903231328.4CC787FDE1@mail.yyyy.it> Queued mail for delivery)
Sep  4 01:13:50 NewWeb postfix/qmgr[23903]: 4CC787FDE1: removed

To Gmail:

Sep  4 01:23:26 NewWeb postfix/cleanup[2938]: EA0FF7FDE1: message-id=<20130903232302.EA0FF7FDE1@mail.yyyy.it>
Sep  4 01:23:26 NewWeb postfix/qmgr[23903]: EA0FF7FDE1: from=<noreply@yyyy.it>, size=357, nrcpt=1 (queue active)
Sep  4 01:23:26 NewWeb postfix/smtp[2947]: EA0FF7FDE1: to=<xxxx@gmail.com>, relay=gmail-smtp-in.l.google.com[173.194.70.27]:25, delay=39, delays=38/0/0.08/0.41, dsn=2.0.0, status=sent (250 2.0.0 OK 1378250599 7si16540202eeu.278 - gsmtp)
Sep  4 01:23:26 NewWeb postfix/qmgr[23903]: EA0FF7FDE1: removed
Sep  4 01:23:32 NewWeb postfix/smtpd[2933]: disconnect from localhost[127.0.0.1]

The email seems to be sent, but it never goes through hotmail. If you need some other configuration files, I can add them in comments.

Thanks to anyone help me figure out this...

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1  
Your messages were delivered. Check your spam folder. –  Michael Hampton Sep 3 '13 at 23:54
    
No email in the spam folder... –  CappyT Sep 5 '13 at 15:09

3 Answers 3

up vote 2 down vote accepted

Hotmail randomly blocks some IP addresses in order to get you to sign up for there Junk Mail Reporting Partner Program. If you don't you can get error with your mail returned with a message like this:

host mx2.hotmail.com[65.54.188.72] said: 550 SC-001
(BAY004-MC1F54) Unfortunately, messages from xxx.xxx.xxx.xxx weren't sent.
Please contact your Internet service provider since part of their network
is on our block list. You can also refer your provider to
http://mail.live.com…il/troubleshooting.aspx#errors. (in reply to MAIL
FROM command)

To fix this you can fill this form (I believe this one will allow the IP's to send to your address on hotmail):

https://support.msn.com/eform.aspx?productKey=edfsmsbl2&ct=eformts

or this one (this one should allow the server(s) to send to all hotmail addresses):

https://support.msn.com/eform.aspx?productKey=edfsjmrpp&ct=eformts

and if you have a range of IP's with clients VM (where the mails are not your domain), you will need to sign up to Smart Network Data Service here:

https://postmaster.live.com/snds/index.aspx

and enter your servers IP range. Microsoft is making it complicated to get people to sign up, or pay for anti-spam services when people are afraid they might be blacklisted.

You can also verify your blacklisting status here:

http://www.anti-abuse.org/

or here:

http://mxtoolbox.com/

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My experience was the same. I submitted Microsoft's delisting form 3 times. The first two included a canned response, "We were unable to identify anything on our side that would prevent your mail from reaching Outlook.com customers.". Then we joined JMRP before submitting a 3rd time. I don't know if JMRP was required, but on our 3rd submission MS promptly worked with us and resolved our issue. I've included a link to the delisting form. support.live.com/eform.aspx?productKey=edfsmsbl3&ct=eformts –  Jamey Taylor Dec 17 at 16:47

CappyT is right. The problems comes from the hotmail servers. That's unbelievable, see also the very poor anwers from microsoft to this: microsoft answers

I experienced this problem also with my servers (that are not blacklisted in no way), my messages are perflectly authenticated (spf, dkim) and well formatted. I send emails to thousands of people. Checkink the log, i see:

postfix/smtp[15617]: B05C066C0E: to=EMAIL, relay=mx1.hotmail.com[65.54.188.110]:25, delay=2.8, delays=0.07/0.01/1.2/1.5, dsn=2.0.0, status=sent (250 EMAIL Queued mail for delivery)

This is the same as an Ok acknowledgment for me. I don't receive a bounce responce and the message is never delivered. Conclusion: I have to say to our members to go away from hotmail

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Did you find any solution for the problem except telling the customers to move away from hotmail? –  t.niese Sep 23 at 10:26

250 <20130903231328.4CC787FDE1@mail.yyyy.it> Queued mail for delivery

Server reponded with normal status (250) and informed, that your message was received by the server and queued. Maybe it's in spam, or maybe is blocked, but still with status 250.

To avoid such problems, setup SPF and DKIM.

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