On 07/01/18 18:11, Yuval Levy wrote:
> I am still digesting the response received.  In essence, they say that
> they "have reviewed [my] IP(s) (XXX.XXX.XXX.XXX) and determined that
> messages are being filtered based on the recommendations of the
> SmartScreen® Filter.

You might be interested in this link, then:
https://mail.live.com/mail/junkemail.aspx

> 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 [them] 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."

So to put it simply, they're basically saying that their black box
thinks that your IP(s) are sending SPAM.

I can speculate that this might be a case of your emails somewhat
resembling emails they have seen from scammers that claim to be legal
representatives in order to further some scam or another.  This is only
a guess though, I could be completely wrong here as I really don't know
anything more about Microsoft's black box than you do.

> Is it possible that Microsoft discriminates against my emails because I
> do not use HTML format?  That's an *allegation* I am willing to make at
> the right place and time.

Highly unlikely.  There is absolutely nothing wrong with sending plain
text emails, I do so myself and don't have problems with MS receiving them.

> Is it possible that Microsoft discriminates against my emails because
> they are sent using FLOSS client software and O/S?  That's another
> *allegation* I am willing to make at the right place and time.

Also highly unlikely, I do the same and don't have issues.  Also it's
all about following the SMTP protocol correctly, which has nothing to do
with whether the software used is FLOSS or proprietary or anything
in-between.

> Is it possible that Microsoft discriminates against my emails because
> they show that the IP address from which the mail client sent the
> message to the sending MTA is dynamic/residential but there is no trace
> of that IP address in consumer databases because I adamantly block any
> attempt to track web behaviour at that IP address?  Another *allegation*
> that I am willing to make at the right place and time.

This shouldn't be the case, but if your submission server resides on a
dynamic IP address then this could very well be the case.  I say
"shouldn't", though, because there have been known cases of anti-spam
appliances in the past that do deep inspection of Received headers and
compare IP addresses found in them against policy blacklists.  These
types of blacklists are designed only to be used against the IP address
of the connecting server, not IPs found in headers.  That said, I don't
think that Microsoft is doing that.

> Is it possible that Microsoft discriminates against my emails because I
> am trying to run a law practice free from Microsoft software and I have
> been advocating vocally for access to legal services through software
> that works on more than one platform?  Conspiracy theory.  I will not go
> that far.

As others have already pointed out, I imagine that you're not big enough
for Microsoft to even care.  I really would not put any malicious intent
here.  There is an old saying, "Never attribute to malice what can
adequately be explained by incompetence."  In this case I think it's
just that you've tripped some stupid anti-spam measure in their black
box and it now thinks that you're a spammer and unfortunately for you
you're too small for Microsoft to care at all about you so they've given
you a cookie-cutter response and file the complaint away in their
virtual rubbish bin.

> Bottom line, I think the problem is more ethical than technical.

I certainly think it's technical on their part, but if by ethical you
mean that Microsoft just doesn't care enough about you to want to solve
your problem then you're probably right.

>  There
> is nothing wrong with how my Postfix server and mail client are
> configured, but Microsoft decides that it does not like some nebulous
> characteristics of my emails on a message by message basis and
> (a) substitutes its algorithmic judgment for the judgment of the
> recipient as to what is or is not desirable email;
> (b) destroys such message without warning or notice to the recipient;
> (c) deceives the sender with the misleading statement to the sender's
> server that the message has been received and is queued for delivery
> (250) when in fact it has been zapped.

I certainly agree with you on these points, but again I don't read
anything malicious against you personally.

> I am still thinking how to react.  For now I will advise my clients that
> I cannot communicate by email if they are using Microsoft services.

I would suggest, as others have, that if you cannot resolve this
directly then you use a relayhost for messages that go out to Microsoft
clients, then you should at least be able to get your mail through.


Good Luck,


Peter

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