troubleshooting Question

Office 365 email to 3rd party bounce back due to "Misconfigured PTR record"

Avatar of Alexandre Michel
Alexandre MichelFlag for Australia asked on
Microsoft 365DNSAntiSpamEmail ServersEmail Protocols
15 Comments2 Solutions18131 ViewsLast Modified:
Hi Experts

Here is the setup
1. Sender is using Office 365
2. Sender workplace does not have fixed IP.
3. Sender's workforce is mobile. Could work from many different locations including wifi hotspot, 3G/4G, client wifi, etc
4. ONE Recipient mail server is refusing email from sender. Office 365 (sender mail server) sent an NDR message to the sender - see below

Question 1: Is the recipient mail server reacting to where the emails come from (Office 365 server) or where the emails were created (the IP of where the Outlook was when the email was created)?

Question 2: Is there a solution to this issue? The sender's workplace ISP does not offer fixed IP. The "Outlook's ISP" can change on a daily basis.  So is there a solution to this issue?

Your message to peter@recipient.com couldn't be delivered.

A security check at recipient.com failed due to misconfigured settings at sender.com.

Action Required: Misconfigured PTR record      

How to Fix It
The recipient's email server at recipient.com performed a security check against your message and the check failed. To fix this, forward this non-delivery report (NDR) to your email admin.

Was this helpful? Send feedback to Microsoft.
________________________________________

More Info for Email Admins
Status code: 550 5.7.363

It appears that the recipient's email server at recipient.com performed a reverse DNS (rDNS) lookup security check to verify that the IP address the message is coming from is associated with the sending domain, and the lookup failed. It appears that the pointer (PTR) record for sender.com isn't set up correctly.

Set up or fix your domain's PTR record - If you're the admin for sender.com, work with your DNS hosting provider (your domain registrar, Web hosting provider, or ISP) to correctly set up a PTR record for your domain. If you're using Office 365 to manage your DNS records note that PTR record creation and management isn't supported in Office 365, so you'll have to change your DNS management to a DNS host outside Office 365. Refer to this article for more information and instructions: Change how DNS records are managed with Office 365.

Unfortunately, Office 365 Support can't help you fix these kinds of externally reported errors because Office 365 doesn't support PTR record management.
Original Message Details
Created Date:      12/08/2016 3:54:42 AM
Sender Address:      john@sender.com

Recipient Address:      peter@recipient.com

Subject:      test email


Error Details
Reported error:      550 5.7.363 Remote server returned sender verification failed -> 550 Verification failed for <john@sender.com>;No Such User Here;Sender verify failed
DSN generated by:      HK2PR04MB1700.apcprd04.prod.outlook.com
Remote server:      ctp8kvm5.webhosting.openconnect.com.au

ASKER CERTIFIED SOLUTION
Jian An Lim
Solutions Architect
Join our community to see this answer!
Unlock 2 Answers and 15 Comments.
Start Free Trial
Learn from the best

Network and collaborate with thousands of CTOs, CISOs, and IT Pros rooting for you and your success.

Andrew Hancock - VMware vExpert
See if this solution works for you by signing up for a 7 day free trial.
Unlock 2 Answers and 15 Comments.
Try for 7 days

”The time we save is the biggest benefit of E-E to our team. What could take multiple guys 2 hours or more each to find is accessed in around 15 minutes on Experts Exchange.

-Mike Kapnisakis, Warner Bros