On 8/20/2018 6:36 PM, mich...@robinson-west.com wrote:
> I am setting up postfix and dovecot on a virtual private server running 
> CentOS 7 remotely. What do I have to implement so that gmail won't flag email 
> from my server as insecure?

I've been through this in the last year even though my server has been
operating for years.

Here's a checklist:

1) Make sure your outgoing IP is static, has valid reverse DNS, SPF and
   DKIM set up.  This is necessary but not sufficient.

2) Check a site like

      https://www.robtex.com/?ip=nn.nn.nn.nn&blacklists=1

   substitute your server IP for nn.nn.nn.nn.  You will probably get a
   few hits on some little-used draconian DNSBLs that block your entire
   /18 or /16 netblock but that's unavoidable.  They don't seem to
   affect much.  What you must avoid (and resolve if present) is any
   IP-specific blacklisting.

3) Email a number of different gmail correspondents, then contact them
   by other means and ask them to mark "NOT SPAM" anything from your
   server that gets routed to SPAM folders.  Gmail seems to value its
   users' classification of SPAM.  Once you've gotten several (don't
   know how many, in my case less than half a dozen) users to mark your
   email as NOT SPAM they seem to pass it through to everybody.  You'll
   have to follow up with gmail correspondents for a month or two.



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