Solved

SMTP relay (IIS 6) with Office 365 not working - 550 5.7.1

Posted on 2014-04-16
2
4,023 Views
Last Modified: 2014-05-09
Hi,

I hope someone can help me to get an SMTP relay working. At the moment, we are in a hybrid Office 365 setup with 2007 and 2010 on-premise Exchange servers. We are looking to decommission these as soon as possible so I am trying to get an SMTP relay working and have more or less followed these instructions: http://www.getoffice365trial.com/configure-office-365-smtp-relay/

To test this, we have a UPS that sends notifications via SMTP. I changed the SMTP server address to the IP of the machine I have setup as the relay and, according to the UPS, the mail sends. But it's never received. If I look at the logs, it shows:

132.245.210.2 - OutboundConnectionResponse [16/Apr/2014:13:24:29 +0000] "- -?250 2.1.5 Recipient OK SMTP" 0 22
132.245.210.2 - OutboundConnectionCommand [16/Apr/2014:13:24:29 +0000] "BDAT -?2391 LAST SMTP" 0 4
132.245.210.2 - OutboundConnectionResponse [16/Apr/2014:13:24:34 +0000] "- -?550 5.7.1 Client does not have permissions to send as this sender SMTP" 0 65

Open in new window


I think this is because, in the outbound security section on the relay I have it set to "Basic Authentication" and the account details that are in there probably don't have permissions to send as the address the UPS sends as. I tried changing this from Basic Authentication to Anonymous Access and get this in the logs:

157.56.253.6 - OutboundConnectionCommand [16/Apr/2014:13:48:17 +0000] "MAIL -?FROM:<> SIZE=2364 SMTP" 0 4
157.56.253.6 - OutboundConnectionResponse [16/Apr/2014:13:48:22 +0000] "- -?530 5.7.1 Client was not authenticated SMTP" 0 38
157.56.253.6 - OutboundConnectionCommand [16/Apr/2014:13:48:22 +0000] "QUIT - SMTP" 0 4

Open in new window


Also, if I just drop a test file into the pickup folder it generates a .bdr file in the Badmail folder that states:

U n a b l e  t o  d e l i v e r  t h i s  m e s s a g e  b e c a u s e  t h e  f o l l o w  e r r o r  w a s  e n c o u n t e r e d :  " E r r o r  i s  p r o c e s s i n g  f i l e  i n  p i c k u p  d i r e c t o r y . " .


T h e  s p e c i f i c  e r r o r  c o d e  w a s  0 x C 0 0 4 0 2 C E .

Open in new window


I'll happily provide all the setup details if needed. Can anyone point me in the right direction please?

Thanks in advance.
0
Comment
Question by:ishamsi
[X]
Welcome to Experts Exchange

Add your voice to the tech community where 5M+ people just like you are talking about what matters.

  • Help others & share knowledge
  • Earn cash & points
  • Learn & ask questions
2 Comments
 
LVL 16

Accepted Solution

by:
Enphyniti earned 500 total points
ID: 40007138
the account details that are in there probably don't have permissions to send as the address the UPS sends as

I believe that is your problem right there.  Make sure you are using account credentials for the address you are trying to send as or grant Send-As rights to the creds that you are using.
0
 

Author Closing Comment

by:ishamsi
ID: 40053146
I really should have realised that. Thanks for pointing it out. I now have another SMTP relay problem but I'll post a new question about that. :) Thanks for your help.
0

Featured Post

Migrating Your Company's PCs

To keep pace with competitors, businesses must keep employees productive, and that means providing them with the latest technology. This document provides the tips and tricks you need to help you migrate an outdated PC fleet to new desktops, laptops, and tablets.

Question has a verified solution.

If you are experiencing a similar issue, please ask a related question

Suggested Solutions

Easy CSR creation in Exchange 2007,2010 and 2013
When you’re making plans to join the modern business race, you should analyze various details that may affect your results. Nowadays, millions of businesses are trying to grow into established and appreciated professional enterprises.
In this video we show how to create a Distribution Group in Exchange 2013. We show this process by using the Exchange Admin Center. Log into Exchange Admin Center.: First we need to log into the Exchange Admin Center. Navigate to the Recipients >>…
Established in 1997, Technology Architects has become one of the most reputable technology solutions companies in the country. TA have been providing businesses with cost effective state-of-the-art solutions and unparalleled service that is designed…

732 members asked questions and received personalized solutions in the past 7 days.

Join the community of 500,000 technology professionals and ask your questions.

Join & Ask a Question