outbound weird problem with hotmail

[Romer Romero]

Hello I've been all the afternoon surfing the forum trying to look for a solution with no luck

at my server just 1 costumer can't send emails to hotmail. (the others can) this is the log:


2013-01-24 16:10:25 1TyV05-0006zm-6w <= [email protected] H=localhost.localdomain (my.server.com) [127.0.0.1]:45541 I=[127.0.0.1]:25 P=esmtpa A=dovecot_login:[email protected] S=822 [email protected] T="test 16" from <[email protected]> for [email protected]
2013-01-24 16:10:25 1TyV05-0006zm-6w SMTP connection outbound 1359065425 1TyV05-0006zm-6w costumer.com [email protected]
2013-01-24 16:10:25 1TyV05-0006zm-6w => [email protected] F=<[email protected]> R=lookuphost T=remote_smtp S=1296 H=mx3.hotmail.com [65.55.92.136] C="250 <[email protected]> Queued mail for delivery"

the email is not at the "Mail Queue Manager" that's the weird part. Also the domain is not in /etc/remotedomains and yes it is in /etc/localdomains. I don't recieve returned error emails back and of course I checked the spam folder at hotmail. I recieve the same log message via webmail and thunderbird. and when I check the mail status summary I see them in the relayed message list like this.:

1 localhost.localdomain[127.0.0.1] [email protected] mx3.hotmail.com[65.55.92.136] [email protected]

Thaks for your help and sorry for my english

 

[Infopro]

Everything ok with that customers domain?
/http://www.intodns.com/

 

[Romer Romero]

well, there was a problem. thank you. the other server where the second nameserver is didn't have the zone. now it's fixed. but I still have the problem. same error. when I write to gmail for example I recieve it in the spam folder. I don't know what else to check.

 

[JaredR.]

The only way to know for sure why Gmail or Hotmail considers mail to be spam, is to ask Gmail or Hotmail. Large mail providers have their own policies, and they often do not send anything back in the SMTP transaction that would explain why this is happening. It is most likely happening after the actual SMTP transaction is over, before the mail is put in the user's in-box. The only certain way to know why it happens is to ask them directly. Anything else is really just speculation.

 

[mctDarren]

Romer, do you have DKIM enabled on the account? Check to see if your DKIM is using an older, weak key. I know Gmail has started moving emails to spam that use older (broken, see article here) keys. Also, when you look at the "original code" in Gmail you will see a "(weak)" in the headers that Gmail inserts when DKIM is considered weak.