On Jan 15, 2014, at 10:05 AM, Darren Pilgrim <na...@bitfreak.org>
 wrote:

> On 1/14/2014 4:06 PM, Brandon Applegate wrote:
>> Just saw this in a message tonight.  No idea if this is a transient error
>> or not.
>> 
>> ---
>> host gmail-smtp-in.l.google.com
>> [gmail-smtp-in.l.google.com][2607:f8b0:4002:c01::1a]
>>    said: 550-5.7.1 [2607:ff70:11::11] Our system has detected that this
>>    message does not 550-5.7.1 meet IPv6 sending guidelines regarding PTR
>>    records and authentication 550-5.7.1 . Please review 550-5.7.1
>>    https://support.google.com/mail/?p=ipv6_authentication_error
>> [support.google.com] for more 550
>>    5.7.1 information. t26si2290895yhl.255 - gsmtp (in reply to end of DATA
>>    command)
> 
> I saw a number of these as well but in my case the bracketed IP addresses 
> were malformed.  For example:
> 
> host gmail-smtp-in.l.google.com[2607:f8b0:4002:c01::1a] said: 550-5.7.1 
> [2607:fc50:1000:1f00::2      16] Our system has detected that this 550-5.7.1 
> message does not meet IPv6 sending guidelines...
> 

https://support.google.com/mail/answer/81126?hl=en#authentication
Additional guidelines for IPv6

The sending IP must have a PTR record (i.e., a reverse DNS of the sending IP) 
and it should match the IP obtained via the forward DNS resolution of the 
hostname specified in the PTR record. Otherwise, mail will be marked as spam or 
possibly rejected.
The sending domain should pass either SPF check or DKIM check. Otherwise, mail 
might be marked as spam.

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