I have a VPS and when I send an email, I get a delivery error email with one of the following (the email is not in the spam, it is not being sent at all):

  1. all hosts for 'gmail.com' have been failing for a long time (and retry time not reached)
  2. host alt4.gmail-smtp-in.l.google.com [] retry timeout exceeded

All other domains receive my emails with no problem. mail-tester grade is 10/10. MXToolbox is ok except for

Reverse DNS is not a valid Hostname: Your Reverse DNS Record (PTR) is not a valid host name. According to email sending best practices, a PTR Record should be a valid host name. If the PTR Record is not a valid hostname, there is a likelihood that you will experience email delivery issues with anti-spam services.

Is Google (and only Google) so sensitive about this issue that it can fail solely because of this issue? Can it be that Gmail is blocking my IP?

What frustrates most is that I have no indication about any problem, just a notification saying that the email was not delivered and that it will keep trying... Until it fails completely.

I have no problem receiving emails from Gmail. My mail is not marked as spam. The only issue is with Gmail, other providers work well.

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    Your Reverse DNS Record (PTR) is not a valid host name. well, do you have a valid rDNS entry for your mailserver/domain? In many many many anti-spam applications this is one of the first things checked and I'd assume nearly everyone would reject your mails. Have a look at FCrDNS, for example. – Lenniey Jul 1 at 12:13
  • This problem happens only with Gmail. I do want to mention again that the emails are not going to spam but are not being delivered at all. Where can I check this -> do you have a valid rDNS entry for your mailserver/domain? – Amos Jul 1 at 12:19
  • debouncer.com/reverse-dns-check?ip=111.222.333.444 for example. Or mxtoolbox.com/ReverseLookup.aspx (but they gave you the message, so...) – Lenniey Jul 1 at 12:25
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    "I have a VPS and when I send an email" it is extremely common for VPS subnets to be blocked, use a email service provider like mandrill app, sendgrid,mailgun, amazon SES, etc. something that receives requests over authenticated smtp or api – Jacob Evans Jul 1 at 16:53
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    Possible duplicate of Prevent mail being marked as spam – Jenny D Jul 2 at 9:20

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