On Jul 20, 2010, at 7:46 PM, Hector Santos wrote:

> J.D. Falk wrote:
> 
>> On Jul 20, 2010, at 8:09 AM, Hector Santos wrote:
>>> It seem so random in what seems to be always accepting a transaction but 
>>> intermittently delivered or not.
>> Are you talking about the 4xx replies?  If you check the text of the reply, 
>> there's usually a URL with a bit more information about the reason.  Same 
>> with 5xx, for that matter.
> 
> I have not seen temporary rejects.  All transactions accepted with 250. 
> However, it has been noted by others that YAHOO does employ greylisting (in 
> some form).  But I have not seen the temporary negative reply codes.

It's not the wikipedia definition of greylisting, but they do use 4xx replies 
to control the flow of inbound mail.

>> If you're saying the mail is just disappearing, it's possible that your 
>> users have configured their accounts to delete suspected spam instead of 
>> putting it in the spam folder.
> 
> The issue is that its intermittent and not consistent.  Send a test, with the 
> recipient on the phone, he gets it.  Send another test, i.e, same message 
> with "TEST #2" as subject, it never arrives. Send "Test #3" it may or not 
> arrive, and so on. No pattern.

I remember hearing some years ago that Hotmail's SVM filter had learned that an 
empty message with a subject of "test" was spam.  They've probably fixed it 
since then, but it's a great example of how machine learning can lead to 
entirely logical but unexpected results.  (I'm fairly certain Yahoo! Mail 
doesn't use any Microsoft software, though.)

> However, at some point, we tried the reverse, yahoo to non-yahoo, which 
> arrived each time and then we try sending test messages again. For a moment 
> there, it appeared to work, so we presumed there was a YAHOO user based 
> "auto-white listing" to addresses the user sends mail to.  I jumped on this 
> theory because we have that feature - local users can build an auto-white 
> list just by sending mail to to their "social/business" network.
> 
> But then we try sending "test #4", "test #5" and so on and they done ever 
> arrive or go into any folder.
> 
> Absolutely, no pattern, inconsistent "DISCARDING" and delivery of mail.

Often, filters will be reacting to a system-wide pattern that an individual 
user can't see.  To give an overly simplified and surely incorrect example, if 
a spammer were sending "test #4" all day, then your entirely legitimate "test 
#4" would get caught too.

That said, if the mail is being discarded due to system-wide (rather than 
recipient-specific) filters, I'd personally prefer to see a 5xx reply instead.  
But: their system, their rules.

> I really hope someone with the yahoo story can explain it.

Like everyone else who writes anti-spam software, Yahoo! is not known for 
divulging their secrets.  Though I did work there for a time, everything I've 
written here could be gleaned from public statements and general knowledge of 
the techniques a large mailbox provider is likely to employ.

> I was somewhat watching to see/hear if there was a related to valid DKEY/DKIM 
> Brownie points or something now expected by YAHOO.  But all I know so far 
> about that is that is required by BULK mail senders.  We are not bulking 
> here. just individual single shot messages.

DKIM isn't required to send mail, bulk or otherwise.  Yahoo! does require DKIM 
for non-ISPs to subscribe to their complaint feedback loop, but doesn't 
automatically provide any brownie points.

Single shot messages are always the hardest to diagnose, since you can't see a 
pattern -- and if you send enough to create a statistically significant 
pattern, the spam filters will notice it too.


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