Below is the last email I received from Microsoft regarding the silently
discarded emails. It neatly summarizes the whole interaction, except
the first automated reply that I received on submitting their form. I
hope I managed to attach it to the appropriate discussion thread, if
not, please accept my apology.
-------- Forwarded Message --------
Subject: RE: SRX1410787439ID - Re: Reported deliverability problem to
Date: Sat, 6 Jan 2018 21:59:59 +0000
From: Hotmail Sender Support <[hidden email]>
To: yuval levy <[hidden email]>
My name is Sunish and I work with the Outlook.com Deliverability
We have reviewed your IP(s) (XXX.XXX.XXX.XXX) and determined that
messages are being filtered based on the recommendations of the
Email filtering is based on many factors, but primarily it's due to
mail content and recipient interaction with that mail. Because of the
proprietary nature of SmartScreen® and because SmartScreen® Filter
technology is always adapting and learning more about what is and isn't
unwanted mail, it is not possible for us to offer specific advice about
improving your mail content. However, in general SmartScreen® Filter
evaluates specific words or characteristics from each e-mail message
and weights them, based on their likelihood to indicate that a message
is unwanted or legitimate mail.
Unfortunately, after reviewing the information you provided and in
compliance with our mail policies, we are unable to offer immediate
mitigation for your deliverability issue. However, we have some
specific recommendations for you to consider that can help you to
improve deliverability over time.
Here are some specific recommendations for you to consider:
Brand your mail
Ensure mails are cleanly formatted and clearly identifiable as
originating from your service.
Follow content and formatting best practices
There are numerous Internet resources which offer advice and best
practices, we recommend you refer to these resources for assistance
creating well formatted and more deliverable email.
Highlight Opt In
Clearly mark your emails so that Windows Live Outlook.com customers are
able to identify that they requested or subscribed to emails from your
Ensure your email lists are up to date
Remove those who do not want to receive the emails and consider making
the unsubscribe process more visible to ensure you are only delivering
mail to interested recipients.
Join the Junk Mail Reporting Program (JMRP)
We believe that your recipients are the best indicator that the email
you are sending is wanted. The JMRP program allows you to see which of
your emails Outlook.com users have marked as junk or unwanted mail.
Reviewing the results in JMRP will provide to the most direct
information on what characteristics of your email, customers, and
ultimately SmartScreen®, consider to be unwanted. This helpful feedback
mechanism allows you to ensure that mails being sent from your IP are
not resulting in negative feedback that could impact your sending
reputation. Being vigilant about users who mark your e-mail as unwanted
or the types of messages that are being marked as unwanted can help you
keep mailing lists updated with only interested users and modify future
campaigns. In addition, monitoring user complaints can help you
identify unintended mail traffic or detect a potentially compromised
account sending unwanted mail to your customers. Enroll at
Join the Smart Network Data Services program (SNDS)
The SNDS program provides data about traffic seen originating from your
registered IP, such as mail volume and complaint rates. The data is
built from the log files of the inbound mail machines and other servers
at Outlook.com and Microsoft and represents factual information about
the traffic from your mail servers to Outlook.com users. For more
information about this free program refer to
<https://postmaster.live.com/snds/FAQ.aspx> . To register, please go to
http://postmaster.msn.com/snds/. (Tip: As part of the enrollment
process, you are asked to sign the JMRP program agreement and then send
a response to Support indicating that it has been signed. It's not
uncommon for that step in the enrollment process to be missed.)
We encourage you to take an active role in managing your email
practices and infrastructure. The SmartScreen® filter is not static and
it is possible to improve deliverability over time. Implementing and
maintaining email best practices such as those described above can
We also encourage you to download and apply the industry best practices
found in our Outlook.com Enhanced Deliverability
f80be272fb/enhance_deliver.pdf> white paper.
Outlook.com Deliverability Support Team.
--- Original Message ---
From : "Yuval Levy" Sent : Saturday, January 6, 2018 8:57:33 PM UTC
"[hidden email]" Subject : Re: Reported deliverability
problem to Outlook.com
Thank you for reviewing and investigating the IP submitted.
DETAILED DESCRIPTION OF THE PROBLEM:
A correspondent using an hotmail.ca address and another correspondent
using an hotmail.com address both reported to me this week that they did
not receive emails I sent.
Sender is consistently [hidden email]
SMTP server is consistently MX.XXX.XXX, a virtual server under my
The nature of the email is purely business. Three light PDF files
generated by my word processor and a little bit email body text. No
HTML. A GPG signature using an expired GPG key was attached as well, as
an ascii file.
After receiving that report, I tried to send from [hidden email] to
[hidden email], which is an outlook.com mailbox under my control, a
much simpler email. That email never arrived.
I also tried to send an email from my university's alumni service, that
is provided by Google, to [hidden email]. That email never arrived
Last but not least I sent an email from [hidden email] to
[hidden email]. It arrived. When I replied on it, the reply arrived
to [hidden email].
It is very worrying that in all instances for which I have access to the
SMTP server log, outlook's server replied to my SMTP server with a 250,
giving the impression that the message would be delivered. Instead, the
message has been silently discarded. At the very least I would expect a
return message from outlook to let me know that the message was not
Yuval Levy, JD, MBA, CFA
CONFIDENTIALITY: This message (including attachments, if any) is
confidential and may be solicitor-client privileged. Any unauthorized
use or disclosure is strictly prohibited. Disclosure of this e-mail to
anyone other than the intended recipient does not constitute waiver of
privilege. If you are not the intended recipient, please notify us
immediately and delete it. Thank you for your cooperation.
On 2018-01-06 02:55 PM,
> Dear Yuval Levy
> We have completed reviewing the IP(s) you submitted. The following
> table contains the results of our investigation.
> More information needed
> We were unable to identify anything on our side that would prevent
> mail from reaching Outlook.com customers.
> If you are still experiencing deliverability issues, please reply to
> this email with a detailed description of the problem you are having,
> including specific error messages, and an agent will contact you.
> If this is a new IP space, and you have not yet begun to send mail to
> Outlook.com users, please reply to this email and one of our support
> team members will contact you to collect more information.
> Regardless of the deliverability status, Outlook.com recommends that
> all senders join two free programs that provide visibility into the
> Outlook.com traffic on your sending IP(s), the sending IP reputation
> with Outlook.com and the Outlook.com user complaint rates.
> Junk Email Reporting program (JMRP) When an Outlook.com user marks an
> email as "junk", senders enrolled in this program get a copy of the
> mail forwarded to the email address of their choice. It allows senders
> to see which mails are being marked as junk and to identify mail
> traffic you did not intend to send. To join, please visit
> Smart Network Data Services program (SNDS). This program allows you to
> monitor the 'health' and reputation of your registered IPs by
> data about traffic such as mail volume and complaint rates seen
> originating from your IPs. To register, please visit
> There is no silver bullet to maintaining or improving good IP
> reputation, but these programs help you proactively manage your email
> eco-system to help better ensure deliverability to Outlook.com users.
> Thank you,
> Outlook.com Deliverability Support
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