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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 [74.125.193.26] 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.

Amos
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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](https://en.wikipedia.org/wiki/Forward-confirmed_reverse_DNS), for example. – Lenniey Jul 01 '19 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 01 '19 at 12:19
  • https://www.debouncer.com/reverse-dns-check?ip=111.222.333.444 for example. Or https://mxtoolbox.com/ReverseLookup.aspx (but they gave you the message, so...) – Lenniey Jul 01 '19 at 12:25
  • I got "rDNS if forward confirmed" in the first link. I got "DNS Record Published. DNS Record found" in the other link. – Amos Jul 01 '19 at 12:29
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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 01 '19 at 16:53
  • I was able to send an email to gmail in the past, not sure what happened suddenly. If it was blocked, wouldn't I get a proper message about it? Regarding email service provider you wrote, is it something I can "attach" to my VPS or you mean an external one? btw, I'm able to receive from gmail with no problem – Amos Jul 02 '19 at 08:00
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    Possible duplicate of [Prevent mail being marked as spam](https://serverfault.com/questions/227242/prevent-mail-being-marked-as-spam) – Jenny D Jul 02 '19 at 09:20
  • My mail is not marked as spam. It happens ONLY with Gmail. – Amos Jul 02 '19 at 10:37
  • What is the IP of your VPS? – Barmar Jul 02 '19 at 17:54
  • Here is some more info along with it, maybe it can give a hint: http://multirbl.valli.org/email-test/1aa7b6e88a261b5cdddaef889c941b60393d97ce.html – Amos Jul 02 '19 at 19:51

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