On Fri, 31 Jul 2020 at 21:46, Simon Arlott via mailop <mailop@mailop.org>
wrote:

> Could someone from Microsoft and Yahoo help me resolve this issue with
> 209.16.157.42?
>
> 550 5.7.1 Unfortunately, messages from [209.16.157.42] weren't sent.
> Please contact your Internet service provider since part of their
> network is on our block list (S3150). You can also refer your provider
> to http://mail.live.com/mail/troubleshooting.aspx#errors.
> [AM5EUR02FT039.eop-EUR02.prod.protection.outlook.com]
>
> 553 5.7.2 [TSS09] All messages from 209.16.157.42 will be permanently
> deferred; Retrying will NOT succeed. See
> https://help.yahoo.com/kb/postmaster/SLN3436.html
>
>
> The /24 network that the server is located in was purchased and moved
> from ARIN to RIPE on 2020-06-30 [1]. (Our new ISP was unable to supply
> more than 1 IPv4 address.)
>
> The network hasn't been routed since 209.16.128.0/18 was advertised
> until 2017-12 by the original legacy IP holder [2].
>
> None of the IPs are on any DNS lists, so I can only assume there's some
> kind of "newly announced" restriction or "route origin changed" check
> that is preventing it from being allowed to send any email.
>
>
> Microsoft was previously returning 4xx for 47 hours and then either
> disappearing the email or delivering it to Spam but now just returns
> 5xx. Yahoo has always returned 5xx. Google are accepting messages.
>
> The advice in the URLs in the error messages are meaningless because I
> have no "outgoing emails" to review if they're never accepted. This
> domain has SPF/DKIM/DMARC configured and the network is registered with
> SNDS/JMRP.
>
> I don't get anything but automated or template responses from Microsoft
> or Yahoo support.
>
>
> I have 5 users in total (including myself) and don't operate any mailing
> lists. This issue is frustrating when emails to Sky/AOL/Hotmail/etc. all
> bounce.
>
>
>
>
>
> 1. Aside from the creation date in RIPE WHOIS, here's the RIPE list of
> IPv4 transfers for proof that this was transferred (and when):
>
>
> https://www-static.ripe.net/dynamic/table-of-transfers/inter-rir/incoming-ipv4.json
>
> {"transferred_blocks":"209.16.157.0/24", "date":"30/06/2020",
> "transferType":"POLICY", "from_rir":"ARIN",
> "to_organisation":"Edinburgh Hacklab Ltd"}
>
> 2. https://stat.ripe.net/209.16.157.0%2F24#tabId=routing
>
> --
> Simon Arlott
>

Hi, welcome to the low volume sender reputation club...

See discussions passim where we've exhaustively discussed IP reputation and
deliverability problems, mostly to Outlook/Hotmail with cameos by Google
and Yahoo. The short, brutal answer: MS or Yahoo won't help and don't care,
unless they get complaints from paying customers. This is only practical if
you can get recipients hosted on Outlook.com or paid Hotmail services to
report incorrect junk classifications to their paid support, and even then
there's no magic fix.


Your IP reputation is neutral/unknown due to being a new traffic source,
which is often treated with suspicion. Also, a total lack of historical
traffic from this new IP and domains, plus whatever other factors are used
- you're penalised until you build sufficient 'good' traffic volumes from
your new IP and domains. I appreciate this is paradoxical.

You'll also be penalised as a small operator, like many of us are. For one
of my customers (a normal business who has self-hosted email for over a
decade), It's taken me over a year to mostly stop sporadic auto-junking of
office correspondence, outbound emails to prior contacts, or even replies
to incoming emails sent to to Outlook.com-hosted tenants. All this was
simply because I had to migrate my customer to a new, clean IP - in a
reputable block, supplied by a quality company - whose sending domains have
15+ years of history.


I can see on your IP that the basics like RIPE records and FCrDNS seem
fine. Provided you do all the other usual things (DKIM/DMARC/SPF) and
you're a sensible sender, unfortunately you may have to tolerate
permfails on MS and Yahoo for a while. Consider trying something
like making the first delivery attempt from the new IP, with a forced
redelivery attempt sent from a different 'good' IP you used before, to
gradually familiarise MS & Yahoo systems with your new IP, plus any other
relevant IP address warming techniques.

I find many deliverability and 'warmup' guides skew towards commercial-size
email operations, suggesting totally unrealistic email volumes for us as
small operators. At the moment, self-hosted senders often fall through the
cracks of the reputation algorithms. Incidentally, are you also able to try
sending via IPv6 or only IPv4?

I also have various Outlook.com/Hotmail accounts I use to periodically test
two-way deliverability. It's interesting how the algorithm sometimes learns
selectively which can be very annoying (emails are still junked for other
recipients, but eventually get correctly delivered to inbox but only for
that specific test account - after it's been trained with enough incoming
emails. Amongst the whale senders and commercial operators, at the moment
we're usually too insignificant to be noticed by the algorithms.

For Microsoft deliverability, a frequent suggestion is to first go through
the automated helpdesk to report deliverability issues and request IP
mitigation. Complete the form at
http://go.microsoft.com/fwlink/?LinkID=614866 - ignore the first automated
'ineligible for mitigation' reply and state the case clearly. At this point
a human should review and, with luck, 'mitigate' the IP - no other info
will be given. It may not happen. No idea about Yahoo but I've never
personally had a problem with any client sending email to their systems.

Good luck,
Chris
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