On 26 Jul 2015, at 18:16, Daniele Nicolodi <dani...@grinta.net> wrote:

> Hello,
> 
> I apologize in advance because my problem is not strictly related to
> postfix, but I don't know another mailing list with helpful people with
> enough knowledge of the of the subject.
> 
> I have my personal emails handled by my own setup hosted on a virtual
> private server.  Since a while (I believe it is now a year or so) Gmail
> classifies all my emails as spam. I believe I correctly setup SPF and
> DKIM, and the headers in the messages as received on the Gmail side seem
> to suggest that Gmail correctly validates both of those checks. However,
> this does not not seem to help in making them going through.
> 
> The volume of email I send through this server is extremely low (it
> handles only my personal email and I'm the only active user).
> 
> Currently I'm able to send emails to my address @gmail.com from the
> email address I'm currently using without having them classified as
> spam, but not from any email address having a different local part. I
> believe this is because my @grinta.net email address is white listed for
> my @gmail.com email address.
> 
> Of course, Google does not care about the issue.
> 
> There is something I can do to have my emails accepted by Google?
> 
> Thank you very much.

I am beginning to suspect that, if you're doing everything right in 
terms of configuration and whatnot, your only remaining option is 
basically to ask everyone you send mail to to check their spam folder 
and explicitly mark you as wanted, solicited mail. Google's spam AI 
system just gets it wrong too often these days, and you're basically 
without recourse if you don't have any weight to throw around.

You're certainly not the only one;
http://jacquesmattheij.com/ham-or-spam-gmail-not-to-be-trusted-for-important-mail

And I've seen similar unreliability with the accounts we have for 
testing and the like. Gmail isn't the only one either, we're seeing 
mail disappear within Hotmail's infrastructure as well, and it's pretty 
much impossible to get them to acknowledge this as a problem.

I would however have another look at your DNS configuration. Here's the 
relevant header;

==
Received: from zed.grinta.net (grinta.net [109.74.203.128])
        by english-breakfast.cloud9.net (Postfix) with ESMTP id ABBED330874
        for <postfix-users@postfix.org>; Sun, 26 Jul 2015 12:16:38 -0400 (EDT)
==

That's already a mismatch that might be throwing them off, triggering 
some kind of classification error. Pick a hostname, not a domain name, 
and stick to that for everything. One (1) hostname that matches every 
which way you might slice it.

So instead of this;

==
$ host 109.74.203.128
128.203.74.109.in-addr.arpa domain name pointer grinta.net.
==
$ host grinta.net
grinta.net has address 109.74.203.128
grinta.net mail is handled by 10 smtp.grinta.net.
==
$ host smtp.grinta.net
smtp.grinta.net is an alias for grinta.net.
grinta.net has address 109.74.203.128
grinta.net mail is handled by 10 smtp.grinta.net.
==
$ host zed.grinta.net
zed.grinta.net is an alias for grinta.net.
grinta.net has address 109.74.203.128
grinta.net mail is handled by 10 smtp.grinta.net.
==

Make everything 'zed.grinta.net', forward and reverse, including your 
MX record, and create CNAME records for your convenience, such as mail 
client configuration. If you need an A apex record, just create that 
separately, don't use it for sending mail.

HTH,
Joni


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