Hotmail is rejecting email from a digital ocean droplet

Question

I have setup my site on Digital Ocean and point the Domain name "A" record to the Droplet IP.

Emails sent by the site are being received in Gmail and other email clients ( SPAM Folder ) but it does not reach at all to outlook.com / hotmail.com email address.

I understand that i have only changed the "A" and "WWW" record of the domain name and now i am sending emails from the droplet, which is somehow not right. What configuration i need to do on the server so the emails sent from my server are trust worthy.

Header of a test email received in Gmail.

Received-SPF: neutral (google.com: 46.101.217.71 is neither permitted nor denied by best guess record for domain of register@riyali.com) client-ip=46.101.217.71;
To: gtemailtesting@gmail.com
Subject: test
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8; format=flowed; delsp=yes
Content-Transfer-Encoding: 8Bit
Sender: register@riyali.com
From: register@riyali.com
Message-Id: <20160526085540.D27361408BB@riyal.com>
Date: Thu, 26 May 2016 04:55:40 -0400 (EDT)

this is a test message

Server Log ( when sent to hotmail):

May 26 05:16:38 riyali postfix/pickup[30639]: E1A1B1408BB: uid=1000 from=<register@riyali.com>
May 26 05:16:38 riyali postfix/cleanup[31632]: E1A1B1408BB: message-id=<20160526091638.E1A1B1408BB@riyal.com>
May 26 05:16:38 riyali postfix/qmgr[31707]: E1A1B1408BB: from=<register@riyali.com>, size=478, nrcpt=1 (queue active)
May 26 05:16:40 riyali postfix/smtp[31634]: E1A1B1408BB: to=<xxx@outlook.com>, relay=mx1.hotmail.com[65.54.188.72]:25, delay=1.2, delays=0.02/0.01/0.53/0.6, dsn=2.0.0, status=sent (250  <20160526091638.E1A1B1408BB@riyal.com> Queued mail for delivery)
May 26 05:16:40 riyali postfix/qmgr[31707]: E1A1B1408BB: removed

Server Log ( when sent to gmail ):

May 26 05:25:33 riyali postfix/pickup[30639]: 7D8B91408BB: uid=1000 from=<register@riyali.com>
May 26 05:25:33 riyali postfix/cleanup[31719]: 7D8B91408BB: message-id=<20160526092533.7D8B91408BB@riyal.com>
May 26 05:25:33 riyali postfix/qmgr[31707]: 7D8B91408BB: from=<register@riyali.com>, size=471, nrcpt=1 (queue active)
May 26 05:25:34 riyali postfix/smtp[31721]: 7D8B91408BB: to=<gtemailtesting@gmail.com>, relay=gmail-smtp-in.l.google.com[173.194.65.27]:25, delay=0.84, delays=0.02/0.01/0.35/0.46, dsn=2.0.0, status=sent (250 2.0.0 OK 1464254734 ad7si17051750wjc.239 - gsmtp)
May 26 05:25:34 riyali postfix/qmgr[31707]: 7D8B91408BB: removed

Hmm. That email has not been rejected, it has been "queued". This has a special meaning; it means your mail has not been delivered to its final destination, and the mail server will have to deliver it onward later. Wait five days to see if the mail shows up; if it doesn't, then complain to Hotmail. — Michael Hampton, May 26 '16 at 09:24

score 0 · Answer 1 · answered May 27 '16 at 19:36

You SPF Record is being recorded as neutral, these means that you most likely don't have your SPF set up, which you can see here: Your SPF Record. You can use this SPF Wizard to create one. But I think all you need your SPF record to say is.

v=spf1 mx ~all

This might not solve your problem, but it puts you on the right path. You're also not signed up for Hotmail's Junkmail filter program nobl.junkemailfilter.com1 , as I can see you're not whitelisted when scanning for it. You can sign up here Microsoft's SNDS program - Click the Junk Mail Filter program on the left.

You might have other issues, which I can't see I think your rDNS is set up correctly, but you should send an email to mailtes@unlocktheinbox.com to confirm.

A lot of times an IP can be on an internal blacklist, I think Hotmail uses Symantec, but I scanned your IP their and nothing showed up. But that doesn't mean you are on their internal blacklist. I hope this helps a little.

Use this, with the server IP in the appropriate place. Change soft fail ~ to hard fail - at some point once this is tested : v=spf1 ip4:SERVER_IP_ADDRESS_GOES_HERE a mx ~all — Tim, May 27 '16 at 19:52

Hotmail is rejecting email from a digital ocean droplet

1 Answers1