Are you using DKIM on outbound email?  That should help:
https://en.wikipedia.org/wiki/DomainKeys_Identified_Mail

Are you doing any forwarding from your personal domain to gmail
addresses?  If so, setting up SRS on outbound email can help:
https://en.wikipedia.org/wiki/Sender_Rewriting_Scheme

Also, does the IP your mail server lives at show up on any RBLs or have
a poor senderbase reputation?

In the last six months, the expected minimum level of anti-spam features
effectively required by mail servers has gone up a lot.

--Ted

On 3/12/2015 9:04 PM, Matt Lawrence wrote:
> Apparently gmail is delivering some mail from me marked as spam and
> trashing a lot of the rest.  This is a horrible violation of the RFCs
> and it's causing me some real problems in my life.  How do I get them to
> quit doing such evil things?  I own my own domain and mail server and
> I'm the only one on it.  The volume is very low. And, my gmail account
> forwards to this account as well.  So, WTF Google?
> 
> -- Matt
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