This is an interesting topic - it's one I'm affected by. I operate web services and mail servers for a small number of commercial clients, and the opaque (and seemingly erratic) classification criteria for emails is causing me sleepless nights at the moment.
Real world case study: in the past year or so, one of my clients, in particular the company's Managing Director, has experienced multiple deliverability issues to various disparate recipients. This company operates in the media and commodities sectors, so relies heavily on reliable email operation to conduct business with contacts around the world. Until about 18 months ago, emails making it to their recipients was never an issue; I've provided and personally managed email services for this client for over a decade. Of late, the common factor in every deliverability issue is that all recipients seem to be O365/Microsoft MSP customers. After an apparently successful initial delivery, emails are silently junked or, as happened last week, marked with a sufficiently high PCL (5) to be auto-junked as phishing (?!). I only found this out after using an alternate address to email the recipient who was helpful in providing some headers, but was unable to assist further. It's so incredibly frustrating. As others have described, the content of emails which get dropped is fairly standard business to-and-fros. In some cases, correspondence has occurred for some time before the Outlook servers start classifying the mails as junk - seemingly arbitrarily. The prior chain of correspondence being established between my customer and a recipient on an Outlook-hosted account appears to mean nothing once the filters go super-aggressive -- I can't see any reason for it happening. My customer's recipients are not the kind of people who will hit "spam" on his emails, they're invariably longstanding correspondents. The most frustrating thing is that there's no feedback from the Outlook MTAs when these drops occur. I can understand this for some reasons, but still find it remarkably frustrating from a support standpoint. I can't even detect that autojunks are happening (and file the requisite deliverability reports), so the problem continues undetected. We've tried all sorts over the past couple of months: adding to safe senders, discussing with corporate admins, filing deliverability reports to Microsoft etc. We've gone so far as to simplify the email content and means by which customers have been sending emails - e.g. plaintext only, excising all signatures, removing images and so on, even ensuring that the tone of language and the wording is as 'good' as it possibly can be to avoid being erroneously considered as junk. Despite weeks of investigation and testing, all this seems to have made no meaningful difference. Entire domains or sending IPs aside, do individual senders somehow accrue an unshakeable 'label of untrustworthiness' which somehow biases all future emails to be wrong or overly harshly categorised? Any apparent resolution following a deliverability report only seems to fix delivery for the specific recipient's organisation - if at all - the problem invariably happens again with another organisation at a later date. There's never been any feedback to me via any of the Microsoft programmes or my given contact details when my client's business emails start getting junked. The SNDS and JMRP portals are effectively useless for smaller volume senders. For example, my servers' IPs generate insufficient volumes to Microsoft/Outlook/Hotmail recipients to generate statistics via SNDS (except for "all of the IPs have normal status"), despite a steady flow of emails to and from MTAs around the world without issue. My JMRP registrations are active but have never sent me any negative feedback, so I'm confident nothing has been flagged as junk by a customer. In the meantime, my server IP reputations, checked across multiple services appear fine (caveat that senderscore is N/A as they've seen insufficient volume to make a judgement, ironically). All other technicals like spamassassin scoring on representative sample and test emails (all totally fine), consistent IP PTR, SPF, DKIM and DMARC come back as 100% OK, and I've assiduously checked and double-checked everything. --- There's a lack of useful information for senders who are attempting to investigate deliverability issues. Obviously the MS secret recipe for categorising spam, phishing and general junk can't be fully explained - but more detailed guidance and better reporting of dropped emails from otherwise-valid senders (borrowing a domain's SPF return path, or even via JMRP abuse reporting details?) would be a valuable improvement. For smaller operators like me, it's becoming so difficult to guarantee consistent email delivery to Microsoft/Outlook customers, who seem to be increasing in number due to O365 / hosted Exchange migration, that I'm starting to feel like I might be forced out of this business despite doing absolutely nothing wrong and ensuring my own customers adhere strictly to my terms of use (no spam, junk or abuse - authorised access for their business purposes only). I don't want to have to consider migrating my customers to whitelabel mail providers, that seems mad, but I'm yet to find an obvious resolution. I've already fulfilled every requirement I can find to demonstrate my systems only host reputable senders. I have no issue with being fully compliant with best practice, and I strictly monitor the service I provide for any potential abuse or misbehaviour. At the moment, I have absolutely no idea what else I can do when emails get silently ignored or junked by Microsoft email services, I've tried everything I can think of. Misclassification of emails by the Outlook/O365 MTAs causes significant business disruption - and embarrassment for both me and my customers. Despite having 'ticked all the boxes' to indicate I'm a reputable sender it seems it's never enough for Microsoft. I'd be interested to hear from other smaller operators who also see the problems my client and I are experiencing, particularly if they've found any means to more permanently resolve the misclassification issues. Regards Chris On Thu, 18 Apr 2019 at 22:29, Michael Rathbun <m...@honet.com> wrote: > On Thu, 18 Apr 2019 20:06:41 +0000, Michael Wise via mailop > <mailop@mailop.org> wrote: > > >Why in the *WORLD* would you think that INBOX placement is based on such > a small set of factors...? > > Every culture or area of endeavour develops its own set(s) of legend and > lore. > > It is not uncommon, for instance, to see solemn admonishment from "experts" > never to flip your steak more than once on the grill, and always to "sear > to > seal in the juices", even though lab research and experience tell us that > both > dicta are false. > > mdr > -- > "Après moi le déluge." -- Louis XV > "Until then just jiggle the handle." -- Brooke McEldowney > > > _______________________________________________ > mailop mailing list > mailop@mailop.org > https://chilli.nosignal.org/cgi-bin/mailman/listinfo/mailop >
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