I have problem with delivering mails to GMail from a new server setup with configured exim4.

Messages sometime passed to gmail spam folder. But sometimes it rejects immediatelly. I have attached a success of incoming message to gmail.

Here is message source: http://dpaste.com/0KT384Z

I have tried disable ipv6 in exim4 without socuces. GMail already have in logs my pubic IPv6.

BUT. I have a right PTR and SPF records which shows in source as PASS.

I have no any ideas where I can get a help. I have used a google support page for get a support from google. but no any answers got in 10 days...

I dont know what I can todo. Can anyone helps me?

UPDATED: Source of returned mail http://dpaste.com/3STSAMW.txt , here also is a reason why it's returned. The DMARC, SPF, and PTRs of my server IP is normal and displayed in delivered emails as PASS. Here is a test result from mail-tester.com: https://www.mail-tester.com/test-uyg3k

PROBLEM SOLVED The real problem was at Hetzner IPs, a lot of them are blacklisted, if you remove it with manual request to blacklist admin. GMail does not remove, and consider that IPs as unwanted. After got a really clean IP which never was in blacklists all seems fine.

  • Something is off with that MUA. Roundcube 1.2.3 is ancient. – anx Feb 10 at 17:55
  • Which MUA I need to use. I have no ideas. Just a custom one? – Николай Шехавцов Feb 10 at 18:16
  • Changed MUA to just "hosted.pw", now emails just in SPAM folder of gmail. The text message which goes to SPAM I already put in question post. This message appears in spam: dpaste.com/00E4WYG.txt – Николай Шехавцов Feb 10 at 18:29

Haha, I think any message with the subject Привет is a bit suspicious!

But seriously, here is the relevant bit of the SMTP failure:

    550-5.7.1 [2a01:4f8:1c1c:b36a::3      12] Our system has detected that this
    550-5.7.1 message is likely unsolicited mail. To reduce the amount of spam sent
    550-5.7.1 to Gmail, this message has been blocked. Please visit
    550-5.7.1  https://support.google.com/mail/?p=UnsolicitedMessageError
    550 5.7.1  for more information. o18si5225169wrq.380 - gsmtp

If you visit that link, it will explain that you can use Gmail Postmaster Tools to register your domain and get more information about why messages are rejected or marked as spam.

Gmail Postmaster Tools provides senders with metrics on parameters such as reputation, spam rate, feedback loop, etc. It can help you check compliance to the Gmail bulk sender guidelines, as well as identify issues that can cause trouble with the spam filter.

Register at postmaster.google.com, verify your domain, and then check the Delivery Errors Dashboard to find detailed information about why each message is rejected.

  • I already registered at GMail Postmaster tools, but there are always shows the message "Empty data nothing to show" if I check a domain in postmaster tools. Also, changing the subject got nothing, the mail is in spam folder again: dpaste.com/0QQFN51.txt – Николай Шехавцов Feb 11 at 7:16
  • You didn't see a new entry in the postmaster tools after you sent the message? – Michael Hampton Feb 11 at 14:33
  • Yes. I dont see anything, only a message about "No data" and a link to postmaster requirements, in requirements there are a text about a thousands and hundreds mail messages which must be sent from my server. But my users does not send this lot of messages to gmail, it's a small server for few companies which is not sending a lot of emails, just have a working correspondence with clients. Really I can write a script which sends a lot of mails to random gmail recipients, but it looks like something crazy. – Николай Шехавцов Feb 11 at 17:27
  • echo "Subject: Hello my friend, i am glad to hear you." | /usr/sbin/exim4 -v ayanami.dev@gmail.com goes to spam :\ – Николай Шехавцов Feb 11 at 17:34
  • Google really doesn't like you? Are you clicking "Not Spam"? – Michael Hampton Feb 11 at 18:42

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