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There are many similar questions to this one but suggestions are usually pretty generic, like go check your server against that bulk blacklist checker.

So my mail server has a correct SPF record, a PTR and signs all messages with DKIM but still every message goes to spam in Gmail by default.

What can be done in this case?

GMail provides a message that tries to explain why the message end up in spam but it is quite vague: " It contains content that's typically used in spam messages" (http://goo.gl/z2ASq). Linked page has something that proves my suspicions: "Messages sent from accounts or IP addresses that have sent other spam messages". But again, have no clue how to get around this.

Here is an example header:

Received: from mail.somehwere.com ([XXX.XXX.XXX.XXX]) 
by mx.google.com with ESMTPS id y59si1359634wey.46.2012.10.02.07.28.54 
(version=TLSv1/SSLv3 cipher=OTHER); 
Tue, 02 Oct 2012 07:28:54 -0700 (PDT) 
Received-SPF: pass (google.com: domain of ck@somehwere.com designates XXX.XXX.XXX.XXX as permitted sender) client-ip=XXX.XXX.XXX.XXX; 
Authentication-Results: mx.google.com; spf=pass (google.com: domain of ck@somehwere.com designates XXX.XXX.XXX.XXX as permitted sender) smtp.mail=ck@somehwere.com; dkim=pass header.i=@somehwere.com 
DKIM-Signature: v=1; a=rsa-sha256; q=dns/txt; c=relaxed/relaxed; d=somehwere.com; s=default; 
h=Content-Transfer-Encoding:Content-Type:MIME-Version:To:From:Subjectate:Message-ID; bh=LFhHIhWWdKms4f3jo157plOkAJzpbSt1ILThu4epfsI=; 
b=N2raCWyGEvCEp6OJBIpvjWv/yCivYzqTm9go+hLKUH3T5Hi61VvL2cv3c52ivBEzNiOOlzLTWIdK4CfdjKSdStJ1ZD5itVse27P17DTh38b9cXNxXUoK89abTd4GxgO/; 
Received: from localhost.localdomain ([127.0.0.1]:54505 helo=somehwere.com) 
by mail.somehwere.com with esmtpa (Exim 4.80)
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closed as not constructive by Wesley, HopelessN00b, Ward, MDMarra, Joel E Salas Oct 2 '12 at 19:45

As it currently stands, this question is not a good fit for our Q&A format. We expect answers to be supported by facts, references, or expertise, but this question will likely solicit debate, arguments, polling, or extended discussion. If you feel that this question can be improved and possibly reopened, visit the help center for guidance.If this question can be reworded to fit the rules in the help center, please edit the question.

3  
Have you checked all of the generic things? I'm not sure what kind of non-generic help you're after, you didn't even tell us your mail server. –  Dan Oct 2 '12 at 14:33
    
In gmail open and check your headers to see why gmail is sending it to spam. That might be a good hint or somewhere to start. Look at the Received-SPF and X-SPAM areas for sure. To see headers open the email -> click down arrow -> show original –  Robert Oct 2 '12 at 14:57
    
Thanks, I know how to check headers. As I said, there're plenty of similar questions posted here with headers but suggestions are all the same: check agains black lists, add SPF, enable DKIM. I already went through all this and there's no visible clue of why doesn't Gmail like my messages. My primary suspicion is bad reputation of IP address or the whole IP block but I have no idea how to contact Gmail postmaster or to check if this is true even. –  Serg Oct 2 '12 at 16:33
2  
What are the results from the Verifier at Port25‌​? –  Chris S Oct 2 '12 at 19:23
1  
@Serg No need to get defensive, even the best of us make mistakes. Sounds like Google has it out for you, it's probably the content of your messages as GMail tends to bounce blacklisted IPs with a helpful 550 error. You'll have to contact Google and request details. I've heard they're rather slow, but there's really nothing you can do at this point. –  Chris S Oct 2 '12 at 19:57
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2 Answers

If gmail doesn't like your messages your issue is with Google. You need to talk to them.
Refusing to provide us troubleshooting details just ensures that we can't help you.

If you are a bulk sender, this link is for you.
If you're not a bulk sender you want this link
(If that second link doesn't work it's the part of the first link that says "Not a bulk sender? Just sending mail to a friend or business associate? Click here for further help.")

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Obviously, there's no chance of getting a valuable help on this topic here. Thanks, I can google myself. Yes, I searched through other questions like mine posted here and all answers are not going beyond "oh, add DKIM" or "check mxtoolbox". Yes, I read Google help articles already. Thanks, a lot but that's obvious but the my case isn't appear to be so. I'm wondering have you ever tried to contact Google yourself? Won't you share a phone number so I can call too? –  Serg Oct 2 '12 at 19:39
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@Serg I have in fact contacted Google. Using the methods outlined in those two links, which are Google's official channels of support. If you've already tried all the standard solutions and are convinced you've exhausted the help the internet can give (with the paucity of details you've provided us) your next step is the support contact for the provider in question. –  voretaq7 Oct 2 '12 at 19:43
    
Should have said diffent, did you get an answer? I contacted Google myself using these very same links but never heard back from them. –  Serg Oct 2 '12 at 19:59
    
@Serg It took about 3 days in my case. ChrisS also posted an alternate link in his comment on your question which may work better for you. All gmail support (that I've had experience with at least) is handled through these contact forms, and they work reasonably well in my experience. –  voretaq7 Oct 2 '12 at 20:01
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Why don't you send a test email to your gmail account and post FULL headers here, so we can review it (maybe you're overlooking something). The other reason could be that some time before that you (or someone else) did something and Google blacklist you.

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