Why Outlook, Hotmail and Live return 250 Mail queued for delivery, but they never deliver it?

Question

Ok, i've been seeing this the last week, tought it could be gone in a few days by itself, since i wasn't blacklisted and my DNS entries are all ok, but when i try to send e-mails to some user at Outlook, Live or Hotmail, i get this:

2015-02-11 14:54:58 1YLaYz-0000IT-I1 H=localhost.localdomain (higipel.com.br) [127.0.0.1]:41242 Warning: "SpamAssassin as cpaneleximscanner detected OUTGOING smtp message as NOT spam (-1.0)"
2015-02-11 14:54:59 1YLaYz-0000IT-I1 <= teste@higipel.com.br H=localhost.localdomain (higipel.com.br) [127.0.0.1]:41242 P=esmtpa A=dovecot_login:teste@higipel.com.br S=3532 id=5f640648ff1df4f59148f5c9cbbbd67b@higipel.com.br T="Lorem Ipsum" for [privarypreserved]@outlook.com
2015-02-11 14:54:59 cwd=/var/spool/exim 3 args: /usr/sbin/exim -Mc 1YLaYz-0000IT-I1
2015-02-11 14:54:59 1YLaYz-0000IT-I1 SMTP connection outbound 1423673699 1YLaYz-0000IT-I1 higipel.com.br [privarypreserved]@outlook.com
2015-02-11 14:54:59 SMTP connection from localhost.localdomain (higipel.com.br) [127.0.0.1]:41242 closed by QUIT
2015-02-11 14:55:01 1YLaYz-0000IT-I1 => [privarypreserved]@outlook.com R=dkim_lookuphost T=dkim_remote_smtp H=mx1.hotmail.com [65.55.37.72] X=TLSv1:AES256-SHA:256 C="250  <5f640648ff1df4f59148f5c9cbbbd67b@higipel.com.br> Queued mail for delivery"
2015-02-11 14:55:01 1YLaYz-0000IT-I1 Completed

And the weird thing is, i have a few hundred domains under 3-4 IP's at most, but just 4-5 domains are presenting this 'problem'

Anyone found a solution for this yet?

Yes, several times, even a day after i sent the test e-mail, not even a clue of the e-mail in there. :/ — Jorge Ferrari, Feb 11 '15 at 17:19
The email was accepted by the recipient server but it didn't make it to the mailbox. It's got to be caught in a spam filter somewhere on the recipient end. — joeqwerty, Feb 12 '15 at 03:46
There're no filters on account level os the recipient. @sebix, really? :/ No solution until now? — Jorge Ferrari, Feb 12 '15 at 16:54
The solution is to boycott these providers. They talk about free market, let's do it. (When I know of a solution, I'm sure I'll post it here) — sebix, Feb 12 '15 at 17:04
Have a look at this Q&A: http://serverfault.com/questions/536079/cant-send-email-from-postfix-to-hotmail — Alexey Krasheninnikov, Feb 17 '15 at 12:42
SPF and DKIM are important. I haven't tried Live, but GMail junked my emails even after SPF and DKIM. In addition I had to set a DMARC policy, after that my mails started to flow normally. Give DMARC a try. — Bugra Koc, Feb 28 '15 at 09:25
Have you reviewed their faq here: https://mail.live.com/mail/troubleshooting.aspx — Mike B, Mar 18 '15 at 05:55

score 3 · Answer 1 · answered Dec 16 '15 at 13:35

It's because of Microsoft's SmartScreen.

You gotta be in concordance with these topics:

Setup a SPF record
Setup DKIM
Setup a DMARC record
Setup a reverse DNS record
HELO must be a host name not an IP
Make sure that your IP is not on a blacklist
Use a static IP address for your server
Sign up for JMRP and SNDS

I've followed this article, which solved the same problem you're having.

Why Outlook, Hotmail and Live return 250 Mail queued for delivery, but they never deliver it?

1 Answers1