Al,
fwiw, I've confirmed at some point within the past couple of years -
directly with Brandon Long of Google - that, yes, Google does have this
extra after-connection filtering, where a message can potentially be
spam filtered even though the sender's mail server received a "250 OK"
response. How often this happens - it's hard to say - probably in a tiny
fraction of messages that they spam filter - but in my boutique hosting
of a few thousand users - I've anecdotally come across this at least a
few times in the past couple of years, where it was likely a false
positive, but yet the sender got a "250 OK" response. That the message
may have been in the recipients' google spam folder - is something I
already acknowledged, but that's "besides the point". Also, while many
mail hosters ALSO do this filtering technique, I consider this to
/typically/ be an inferior spam filtering practice, although I'm open to
the idea that doing it on a very limited basis might be OK (such as when
an attachment has a /strong/ potential be a zero-day virus that
anti-virus systems are not yet detecting... stuff like that).
Regardless, such "250 OK" false positive being in the intended
recipient's spam folder - is something I referenced in my original post,
and that doesn't impact any of my points.
ALSO - this reminds me - another inferior practice of some of these
largest email providers - including Google - is the lack of support and
willingness/ability to make changes in response to egregious filtering
mistakes. IT staff of their customers are OFTEN told by these large
providers - "it is what it is" - with no willingness to look into SMTP
logs and figure out and fix exactly what went wrong - but level of
service doesn't scale, right? (But yet they STILL charge premium prices
per mailbox - so in spite of this - their REVENUE "scales"!)
Slightly changing the subject and getting back to Paul Vixie's original
post (the post that started this thread) about Google's lack of spam
filtering transparency - unless he's referring to something bad of which
I'm not aware - otherwise, I think he's being a little too picky - spam
filtering is 1/2 sausage factory (if you saw it up close, you'd be
shocked about how crazy it is) - and part front-lines war zone. So, in
summary, spam filtering is "a sausage factory on the front lines of a
war zone". Then Paul Vixie comes along and asks, "where's your TPS
report?" (a reference from the movie "office space" - remember that?) -
and those of us running spam filters are like "dude, we're just barely
surviving, and everything is so fast paced and changing so often - we
can't even think about that TPS report!"
Or, in Paul Vixie's defense, maybe Paul is thinking about the fact that
gmail's outbound spam has been absolutely INSANE the past several
months, with no end of slowdown in sight. It's insane that this has
gotten so little attention in recent months, and that Google keeps
seemingly getting a free pass over that. So there's that, too. And it's
bizarre that so many are so "OK" with that! (or pretend that this isn't
happening?) Or - again - maybe Paul Vixie knows something that many of
us don't know about - regarding Google's mail system! I wouldn't rule
that out.
Rob McEwen, invaluement
On 4/13/2022 10:27 PM, Al Iverson via mailop wrote:
I've seen it happen perhaps twice in twenty years, from what I can
non-scientifically recall. 99.99999% of the time we've had somebody
complain they can't find the mail in their Gmail account, it is
because it's in their spam folder. I'm not particularly worried that
there's some new outbreak of this. Even back in the day, unexpected
internal delays inside of Gmail were more common, and even those were
relatively rare.
To your point, yeah, Microsoft used to be the big bad who would
discard mail after accepting it and that was a super huge pain to deal
with. That seems to be a thing of the past, thankfully.
Cheers,
Al Iverson
On Wed, Apr 13, 2022 at 7:59 PM Jarland Donnell via mailop
<mailop@mailop.org> wrote:
I've seen Microsoft do that very thing many times over the years,
accepting an email but never delivering it. I have to admit, I have not
once witnessed this with Gmail. Given how much volume we do where
customers bring their own domains, I would find it strange to have not
run into it, if it is an actual issue that occurs.
Filtering to the spam folder of course happens with email that received
a 2xx, but I've not yet seen a blackhole. I would be interested in
hearing more about it if anyone has collected any data around it.
On 2022-04-13 19:28, Rob McEwen via mailop wrote:
On 4/13/2022 6:58 PM, Jarland Donnell via mailop wrote:
Out of the 140,244 emails delivered to Google by my customers today,
not a single one has complained of issues with Google rejecting
legitimate email.
Even so, keep in mind the following:
(1) Their most egregious false positives - ARE delivered - they return
a "250 OK" response - but then Google's spam filter does a 2nd round
of spam filtering - AFTER the SMTP connection has completed - and
that's where MOST of their most egregious false positives occur -
partly because the sender THINKS that their message was delivered.
(2) These are OFTEN the types of mistakes that are most often unknown
to the sender - since the sender then never gets back a non-delivery
notification. (and unfortunately not everyone is savvy and consistent
with requesting and monitoring for "read receipts" for important
hand-typed emails!) So then they don't "complain" to their mail hoster
about a problem they don't even know exists! (so their lack of
"complaints" is an inadequate/flawed measurement of success in this
case!)
For example, I have a close relative who was the CFO of a company a
couple of years ago (with hundreds of millions in annual sales) -
before he switched to another company - and what I'm about to describe
occurred AFTER Google's huge move to going "all in" on A.I. for email
processing - and so this company almost lost the renewal of a
multi-million dollar deal because their client's hand-typed messages
were getting 250 OK answers, but were spam-filtered after-the-fact by
Google. The client thought that they were getting dissed by their
vendor - since they didn't get non-delivered notifications for those
emails - and so this client was already in the process of looking for
a new vendor when someone at my relative's (former) company spotted
the false positives from this client in the spam folder at the last
"final hour" and just barely saved the deal.
Of course, that's anecdotal and ALL spam filters have occasional
egregious false positives. But it's just that your "delivered to
Google" might not mean as much as you thought that it meant! It's
possible that a few of those 140,244 emails might not have made it to
the inbox!
--
Rob McEwen, invaluement
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Rob McEwen
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