> On 2 Jun 2021, at 10:17, André Peters via mailop <[email protected]> wrote:

[snip]

> They _DO_ block whole networks (not just subnets within an AS).
> It might not be the case in the example above, but it does happen.

I am reasonably familiar with Microsoft’s anti-spam systems and how they work. 
They do block ranges, and subnets, but anyone claiming that AS(whatever) means 
that MS is blocking autonomous system number(whatever) is flat out wrong. That 
is not what that diagnostic code means. 

> Or silently discarding mail... come on, that's just the worst practice ever.

I silently discard mail all the time. No one, absolutely NO ONE, is entitled to 
my time or attention or mailbox space. That goes double when the mail is 
actively harmful. If MJW says that shouldn’t be happening in the freemail 
domains any longer, I believe him. On the O365 side, individual administrators 
have the ability to discard mail on their own systems for their own domains. 
Neither you nor I have any right to tell those administrators they cannot do 
that. Not our systems, not our rules. 

Look, Microsoft has tons of flaws. They have an aggressive blocking system that 
upsets a lot of senders. They have stupid rules and implementations that I 
don’t think do what they think they do or even what they’re intended to do. I 
think the system has accreted and evolved to a point where not even the folks 
inside Microsoft can tell you why a mail was delivered where it was. I mean, 
that’s been true for more than a decade now. It’s not, somehow, that the folks 
answering sender support mail won’t tell you, it’s that they can’t tell you. I 
suspect that even the system developers couldn’t tell you exactly why a mail 
went to bulk or was discarded or was rejected. 

Machine Learning filters (and it’s all ML filters these days) simply don’t work 
that way. 

With that being said, they try to help senders, much more than a lot of other 
mailbox providers. They were the first company to offer data directly to 
Senders (SNDS). They were one of the first groups to offer FBLs. They are the 
ONLY group I am aware of that actually asks their users directly whether or not 
their spam filters are doing things right in that user’s mailbox. Not some 
random ‘do you like our filters’ but a specific pop up window that says to a 
user: "We put this email in your spam folder (or inbox). Did we get this right?"

It is phenomenally hard for a new sender to break into the MS inbox. For client 
reasons I ended up doing a bunch of tests yesterday and the first mail from my 
IP went to bulk. I hit ’this is not spam’ and the second mail from that same IP 
and sender combination went to the inbox. The third email from a different 
sender but the same IP went to spam. That’s basically what I needed to know so 
I stopped testing at that point. Yeah, Microsoft hates low level senders. 
Microsoft hates new IPs. Complaining on mailop isn’t actually going to change 
anything about that. Complaining to the developers over beer in the pub isn’t 
going to change that. Complaining to the product managers isn’t going to change 
that. O365 is widely used and we’re stuck with it. The free domains are less 
widely used than Gmail but they’re still in the top 5 per volume for most 
mailing lists. 

A few additional facts:

SmartScreen is partially based on the above mentioned ‘did we filter this mail 
correctly’ questions. It’s also based on user complaints. It’s based on the 
content of the mail, it is unrelated to IP or even domain reputation. Call it 
stupid all you want but the reality is: Smart Screen is a measure of how much 
recipients want a particular email stream. If they’re saying they don’t want 
it, then Microsoft is going to listen to what their users tell them. Some of 
the measurements are based on explicit user questions, others are based on user 
interactions with mail. 

Filters are not static, they are adjusting all the time. Sometimes ‘just keep 
trying’ is the right thing to do. Sometimes ‘give it a rest for a week (or 2 or 
3) and let your reputation reset’ is the right thing to do. Sometimes it feels 
like there is nothing the sender can do to change delivery. 

MS users and MS policy makers are about the only folks who are going to be able 
to change what MS is doing. It sucks for those of us who are looking at the 
mail in our outbound queues and going ‘yknow, this person paid for this email 
and MS isn’t letting me deliver it” or “this person probably really wants their 
appointment reminder, but MS isn’t letting me deliver it” or “Auntie susie 
really wants to hear from cousin joan, sucks microsoft doesn’t like this” but 
complaining on mailop isn’t going to change any of that. 

If complaining on mailop fixed MS filters, then they would have been fixed a 
decade ago. We’ve been having this same discussion for that long. 
 
laura

-- 
Having an Email Crisis?  We can help! 800 823-9674 

Laura Atkins
Word to the Wise
[email protected]
(650) 437-0741          

Email Delivery Blog: https://wordtothewise.com/blog     







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