Gmail puts my mail in the spambox

When I first created the mail server everything worked fine and mail landed in the inboxes of Gmail accounts.

Now all of the sudden it keeps landing in Spam boxes. I even added SPF records and an Let’s Encrypt SSL certificate. I found myself blacklisted while only 30 mails have been send as test to myself. I was blacklisted by ivmSIP/24. After requesting removal yesterday, this morning I confirmed they removed me from their blacklist.

What is going and how do I trouble shoot beyond the things I have done?

My mail server scores better then my work mail server which doesn’t land in the spambox.

Results from

  • 3.5 BAYES_99 BODY: Bayes spam probability is 99 to 100%
  • [score: 1.0000]
  • -0.0 SPF_PASS SPF: sender matches SPF record
  • -0.0 RP_MATCHES_RCVD Envelope sender domain matches handover relay domain
  • 0.2 BAYES_999 BODY: Bayes spam probability is 99.9 to 100%
  • [score: 1.0000]
  • 0.1 HTML_MESSAGE BODY: HTML included in message
  • 0.1 DKIM_SIGNED Message has a DKIM or DK signature, not necessarily
  • valid
  • 0.0 T_DKIM_INVALID DKIM-Signature header exists but is not valid X-Spam-Status: Yes, hits=3.9 required=-20.0 tests=BAYES_99,BAYES_999, DKIM_SIGNED,HTML_MESSAGE,RP_MATCHES_RCVD,SPF_PASS,T_DKIM_INVALID autolearn=no autolearn_force=no version=3.4.0 X-Spam-Score: 3.9

Results from MXtoolbox mail server test:

SMTP Reverse DNS Mismatch OK - resolves to SMTP Valid Hostname OK - Reverse DNS is a valid Hostname SMTP Banner Check OK - Reverse DNS matches SMTP Banner SMTP TLS OK - Supports TLS. SMTP Connection Time 1.125 seconds - Good on Connection time SMTP Open Relay OK - Not an open relay. SMTP Transaction Time 3.641 seconds - Good on Transaction Time

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Accepted Answer

You share an IP range with 250 other droplets, this will keep happening. Use something like Mailgun.

Consider using something like Mailgun.

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