Hi,

I have been receiving the below failures when a specific sender sends an email to a user on our Exchange 2007 environment. The email is successful if there is no attachment but fails with attachment. It is also successful if sent to a user on the Exchange 2013 environment. 

As far as I can tell, the sender is using Google hosted email from google.com and postini.com, and also using TLS. I have also tested from other sources such as Hotmail with no issues.

Main issues looks to be Intra-Organization SMTP Send Connector, 550 5.7.1 Requested action not taken: message refused.

If anyone can help, that would be great. Thanks Craig

RunspaceId              : 78b5abc0-1af6-4d28-8dce-f79ed0b60de5

Timestamp               : 23/09/2013 12:11:16 PM

ClientIp                : 172.21.1.222

ClientHostname          : SYDEXG03

ServerIp                : 172.21.1.15

ServerHostname          : SYDEXG02.mydomain.com

SourceContext           : 08D0766A61FD5193

ConnectorId             : Intra-Organization SMTP Send Connector

Source                  : SMTP

EventId                 : FAIL

InternalMessageId       : 10599979286648

MessageId               : <CAH-PWAcb19sJ6GKNzLWbz+KDz9oN0iuZuwMaQg5Aw6k=0a3roQ@mail.gmail.com>

Recipients              : {user@mydomain.com}

RecipientStatus         : {[{LRT=};{LED=550 5.7.1 Requested action not taken: message refused};{FQDN=};{IP=}]}

TotalBytes              : 1030527

RecipientCount          : 1

RelatedRecipientAddress :

Reference               : {<0758f4b5-2237-4e01-9876-7751ac06c870@SYDEXG03.mydomain.com>}

MessageSubject          : TEST email- with attachment

Sender                  : sender@google.com

ReturnPath              : sender@google.com

Directionality          : Undefined

TenantId                :

OriginalClientIp        :

MessageInfo             : 2013-09-23T02:08:50.407Z;LSRV=SYDEXG03.mydomain.com:TOTAL=143|SRT=4|SMR=4|QD=136|S

                          MS=1

MessageLatency          :

MessageLatencyType      : None

EventData               : {[E2ELatency, 146], [Microsoft.Exchange.Transport.MailRecipient.RequiredTlsAuthLevel,

                          Opportunistic], [DeliveryPriority, Low], [PrioritizationReason,

                          AMS:3003838/1048576|ARC:16/50;200]}

• Edited by TwoDogs_Carter Monday, September 23, 2013 8:51 AM

Increase the Max receive size limit on that mailbox and check the status.

User has no limit and receive connector set at 29 MB.

The email size is less than 1MB so does not seem to be a size limit.

Regards

Craig

Hi,

Since the Hotmail can send emails with attachments properly, I think the issue is more related to the Google side. Is it possible to involve an email provider support to check their server settings?

Thanks,

If you have feedback for TechNet Subscriber Support, contact tnsfl@microsoft.com

Hi All,

I have removed the checkbox next to "Offer basic authentication only after starting TLS" on all connectors, frontend, backend, and Exchange 2007. 

I have also disabled Symantec Mail Security on the Exchange 2007 Server, still filtering on all 2013 servers.

Not sure what solved  the issue but it seems to be resolved now.

Thanks for the input.

Craig

• Edited by TwoDogs_Carter 4 hours 49 minutes ago
• Marked as answer by TwoDogs_Carter 4 hours 48 minutes ago