On June 14, 2019 7:43:56 AM UTC, Martijn Brinkers <martijn.l...@gmail.com> 
wrote:
>On 13-06-19 16:43, John Gateley wrote:
>> I recently upgraded my mail server OS (Debian 7 to Debian 9), and at
>the
>> same time got
>> the latest postfix package for Debian 9.
>> 
>> It is hosted in the cloud (Linode), and I completely rebuilt the
>> instance, rather than
>> doing an upgrade. The IP addresses (v4 and v6) are the same. The
>config
>> didn't
>> change (I use ansible to deploy both the software and config - no
>manual
>> steps required).
>> 
>> After the upgrade, I sent a test e-mail to my gmail account, and it
>went
>> to the
>> Junk folder. I moved it to my regular folder, and after that e-mail
>to
>> my gmail
>> account was delivered normally.
>> 
>> My wife sends e-mail to the Washington Post (perhaps hosted by Google
>as
>> well)
>> and they are not receiving her e-mails. They are delivered to the
>mail
>> server, so I
>> strongly suspect they are going to junk as well.
>> 
>> Is there any reason the software upgrade would cause this behavior?
>> I can't think of one, but the timing is very coincidental.
>
>Just a guess. I'm not sure what version of postfix was installed with
>Debian 7 but if it was <= 2.8 could it be that your postfix server now
>favors ipv6 over ipv4?  According to the docs, inet_protocols for <=
>2.8
>was set to ipv4 but is now set to all. There are other reports of
>issues
>with using ipv6 and Gmail (for example
>http://postfix.1071664.n5.nabble.com/disable-ipv6-when-sending-to-gmail-td60672.html)

It was postfix 2.7.

Scott K

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