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I'm setting up a new mail server with postfix dovecot and things are working fine except this strange thing. I'm unable to send email to gmail addresses. The log shows status sent. However, I checked there is no email in gmail mailbox.

Jul  8 13:10:08 example postfix/smtp[5294]: B53B637C233: to=<>,[]:25, delay=2.2, delays=1.5/0.08/0.49/0.14, dsn=2.0.0, status=sent (250 2.0.0 OK 1341727808 nc7si50672387pbc.75)

However, my other account can send to gmail. After several testing, then I found that if I first send email from gmail, then subsequently I can send from my server and email received by gmail.

I don't have this issue with Yahoo. What could be the problem?

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What do your SPF records look like? – Tom Marthenal Jul 8 '12 at 6:24
If I check the mail server domain, it says "v=spf1 a -all". But on, it does not return any record. This is from – BARON'S Jul 8 '12 at 6:33
The e-mail has been accepted by gmail. Go talk to them about why they failed to deliver it to the mailbox. – womble Jul 8 '12 at 6:34

The logs say "sent". So the mail has been sent by you and accepted by Google.

Google then (probably) found your mail "spammy" and discarded it. This is a Google mail processing problem which can only be solved by Google itself. Or send mails that don't look spammy. Follow these instructions for example: E-mail sent with postfix are marked as spam

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