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sorry if this is a duplicate question. I was looking through similar questions but wasn't able to find anything helpful.

One user and only one user is getting an error message back when they try to send mail to an external address. Another user sends the same email to the same address and succeeds. Here is the error message:

From: Microsoft Outlook Sent: Tuesday, June 12, 2018 1:30 PM To: Username Subject: Undeliverable: Subject

exchangeserver.domain.com rejected your message to the following e-mail addresses:

name@extdomain.com (name@extdomain.com)

exchangeserver.domain.com gave this error: Unable to relay

Your message wasn't delivered due to a permission or security issue. It may have been rejected by a moderator, the address may only accept e-mail from certain senders, or another restriction may be preventing delivery.

Diagnostic information for administrators:

Generating server: exchangeserver.domain.com

name@extdomain.com

exchangeserver.domain.com #550 5.7.1 Unable to relay ##

The weird thing is, the user account that is getting blocked is a copy of the account that succeeded.

I've already verified that the "Require that all senders are authenticated" box is unchecked in EMC.

Exchange 2010 is running on a 2008 R2 server.

I am fairly new to Exchange and I am not really sure where to go from here.

If the question lacks detail please let me know what I can add to help clarify.

Update1: The user was not able to send mail to the same email via OWA either. However, they are able to send mail to their personal (non-company) email address.

McITGuy
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  • Have you tried to send the email from OWA? First eliminate if it is some goofy Outlook issue. – Appleoddity Jun 13 '18 at 23:47
  • Does internal mail flow working fine on this effect mailbox? Is it a regular mailbox? How does he send message? From NDR, it indicate that Exchange server cannot reply the message from "he". Is it an Application that uses Exchange to send message out? – Jianfei Wang Jun 14 '18 at 07:04
  • @Appleoddity I'll get them to try sending an email from the OWA today and get back to you. – McITGuy Jun 14 '18 at 14:12
  • @JianfeiWang Yes, internal emails work just fine. It's just a regular mailbox. The user was sending the message from Outlook 2016. – McITGuy Jun 14 '18 at 14:14
  • @Appleoddity Update. The user failed sending the email from the OWA to the same address. However, she can send an email to her personal, non-company email just fine. – McITGuy Jun 15 '18 at 14:17

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