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:
18.104.22.168 - OutboundConnectionResponse [16/Apr/2014:13:24:29 +0000] "- -?250 2.1.5 Recipient OK SMTP" 0 22
22.214.171.124 - OutboundConnectionCommand [16/Apr/2014:13:24:29 +0000] "BDAT -?2391 LAST SMTP" 0 4
126.96.36.199 - 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
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:
188.8.131.52 - OutboundConnectionCommand [16/Apr/2014:13:48:17 +0000] "MAIL -?FROM:<> SIZE=2364 SMTP" 0 4
184.108.40.206 - OutboundConnectionResponse [16/Apr/2014:13:48:22 +0000] "- -?530 5.7.1 Client was not authenticated SMTP" 0 38
220.127.116.11 - OutboundConnectionCommand [16/Apr/2014:13:48:22 +0000] "QUIT - SMTP" 0 4
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 .
I'll happily provide all the setup details if needed. Can anyone point me in the right direction please?
Thanks in advance.