I have an Exchange organisation with multiple Exchange server within a single AD that spans multiple AD sites, with an Exchange server at each site, and each exchange server sends & receives emails for country specific domain name.
I have noticed that when a user at Site A sends an email to an external recipient, but with a user at Site B in CC, then the email is routed from Site A to the Exchange Server at Site B for both recipients. The email is delivered successfully to the internal
user at site B, and queued for external delivery through the external connector at site b.
This is causing problems because the exchange server at site b uses it's own country specific domain name on the external connector, which doesn't match the domain name of the original sender from site a, so delivery to some domains with strict rules are
failing. (gmail is one)
Ideally, the exchange server at site A would route the email to the external recipient to it's own external connector and forward the email for the internal recipient to the exchange server at site B.
The following is a copy of the message tracking logs the from the exchange server at site A (ICMXS04) and Site B (GCMXS04) for a single message id that exhibits this problem.
=================
Site A - ICMXS04
=================
PSComputerName : icmxs04.MyInternal.ADDomain.biz
RunspaceId : e7ce8656-d6f1-44e3-b104-c93a32a6f41a
PSShowComputerName : False
Timestamp : 2/25/2019 10:24:17 AM
ClientIp : 192.168.1.249
ClientHostname : ICMXS04.MyInternal.ADDomain.biz
ServerIp : 192.168.1.249
ServerHostname : ICMXS04
SourceContext : 08D698AE1CD10388
ConnectorId :
Source : STOREDRIVER
EventId : RECEIVE
InternalMessageId : 0
MessageId : <deae6b92a34d466cad83cf3b65085982@ICMXS04.MyInternal.ADDomain.biz>
Recipients : {UserC@ExternalDomain.co.kr, userB@siteB.de}
RecipientStatus : {To, Cc}
TotalBytes : 348378
RecipientCount : 2
RelatedRecipientAddress :
Reference :
MessageSubject : FW: [HEC] REQUEST FOR YOUR COMPANY PROFILE
Sender : userA@siteA.ie
ReturnPath : userA@siteA.ie
Directionality : Originating
TenantId :
OriginalClientIp : 192.168.1.176
MessageInfo : 03I:
MessageLatency :
MessageLatencyType : None
EventData : {[MailboxDatabaseGuid, 0d2421db-6bb6-4764-bd5e-0eb0700e687d], [ItemEntryId, 00-00-00-00-D6-B0
-4B-0D-B4-5E-4E-4C-81-AC-98-04-1B-6A-11-68-07-00-29-55-19-51-CF-31-AB-4B-9C-BF-45-01-9D-95-33
-8B-00-00-00-5A-01-4F-00-00-5C-5D-40-81-93-E3-CF-4B-9C-2A-6F-7F-B2-95-AA-FB-00-03-F7-0D-A3-E7
-00-00], [DeliveryPriority, Normal], [ExternalOrgIdNotSetReason, ]}
PSComputerName : icmxs04.MyInternal.ADDomain.biz
RunspaceId : e7ce8656-d6f1-44e3-b104-c93a32a6f41a
PSShowComputerName : False
Timestamp : 2/25/2019 10:24:18 AM
ClientIp : 192.168.1.249
ClientHostname : ICMXS04
ServerIp :
ServerHostname : GCMXS04.MyInternal.ADDomain.biz
SourceContext : MDB:0d2421db-6bb6-4764-bd5e-0eb0700e687d, Mailbox:f5bda2c2-a75d-4edc-b951-37bbfc5a3a4b,
Event:847063962, MessageClass:IPM.Note, CreationTime:2019-02-25T10:24:16.445Z,
ClientType:MOMT
ConnectorId :
Source : STOREDRIVER
EventId : SUBMIT
InternalMessageId :
MessageId : <deae6b92a34d466cad83cf3b65085982@ICMXS04.MyInternal.ADDomain.biz>
Recipients : {UserC@ExternalDomain.co.kr, userB@siteB.de}
RecipientStatus : {}
TotalBytes :
RecipientCount : 2
RelatedRecipientAddress :
Reference :
MessageSubject : FW: [HEC] REQUEST FOR YOUR COMPANY PROFILE
Sender : userA@siteA.ie
ReturnPath :
Directionality : Originating
TenantId :
OriginalClientIp : 192.168.1.176
MessageInfo : 2019-02-25T10:24:16.445Z;LSRV=ICMXS04.MyInternal.ADDomain.biz:TOTAL=1|MTSS=1
MessageLatency : 00:00:01.9530000
MessageLatencyType : LocalServer
EventData : {[ItemEntryId, 00-00-00-00-D6-B0-4B-0D-B4-5E-4E-4C-81-AC-98-04-1B-6A-11-68-07-00-29-55-19-51-
CF-31-AB-4B-9C-BF-45-01-9D-95-33-8B-00-00-00-5A-01-4F-00-00-5C-5D-40-81-93-E3-CF-4B-9C-2A-6F-
7F-B2-95-AA-FB-00-03-F7-0D-A3-E7-00-00]}
=================
Site B - GCMXS04
=================
PSComputerName : icmxs04.MyInternal.ADDomain.biz
RunspaceId : e7ce8656-d6f1-44e3-b104-c93a32a6f41a
PSShowComputerName : False
Timestamp : 2/25/2019 10:24:18 AM
ClientIp :
ClientHostname :
ServerIp :
ServerHostname : GCMXS04
SourceContext : No suitable shadow servers
ConnectorId :
Source : SMTP
EventId : HAREDIRECTFAIL
InternalMessageId : 159562330013889
MessageId : <deae6b92a34d466cad83cf3b65085982@ICMXS04.MyInternal.ADDomain.biz>
Recipients : {UserC@ExternalDomain.co.kr, UserB@SiteB.de}
RecipientStatus : {}
TotalBytes : 349054
RecipientCount : 2
RelatedRecipientAddress :
Reference :
MessageSubject : FW: [HEC] REQUEST FOR YOUR COMPANY PROFILE
Sender : UserA@SiteA.ie
ReturnPath : UserA@SiteA.ie
Directionality : Originating
TenantId :
OriginalClientIp :
MessageInfo :
MessageLatency :
MessageLatencyType : None
EventData : {[DeliveryPriority, Normal], [ExternalOrgIdNotSetReason, ]}
PSComputerName : icmxs04.MyInternal.ADDomain.biz
RunspaceId : e7ce8656-d6f1-44e3-b104-c93a32a6f41a
PSShowComputerName : False
Timestamp : 2/25/2019 10:24:18 AM
ClientIp : 192.168.1.249
ClientHostname : ICMXS04.MyInternal.ADDomain.biz
ServerIp : 192.168.0.249
ServerHostname : GCMXS04
SourceContext : 08D670BFCFBBCC9D;2019-02-25T10:24:17.367Z;0
ConnectorId : GCMXS04\Default GCMXS04
Source : SMTP
EventId : RECEIVE
InternalMessageId : 159562330013889
MessageId : <deae6b92a34d466cad83cf3b65085982@ICMXS04.MyInternal.ADDomain.biz>
Recipients : {UserC@ExternalDomain.co.kr, UserB@SiteB.de}
RecipientStatus : {}
TotalBytes : 349054
RecipientCount : 2
RelatedRecipientAddress :
Reference :
MessageSubject : FW: [HEC] REQUEST FOR YOUR COMPANY PROFILE
Sender : UserA@SiteA.ie
ReturnPath : UserA@SiteA.ie
Directionality : Originating
TenantId :
OriginalClientIp : 192.168.1.176
MessageInfo : 0cI:
MessageLatency :
MessageLatencyType : None
EventData : {[FirstForestHop, GCMXS04.MyInternal.ADDomain.biz], [DeliveryPriority, Normal],
[ExternalOrgIdNotSetReason, ]}
PSComputerName : icmxs04.MyInternal.ADDomain.biz
RunspaceId : e7ce8656-d6f1-44e3-b104-c93a32a6f41a
PSShowComputerName : False
Timestamp : 2/25/2019 10:24:19 AM
ClientIp :
ClientHostname : GCMXS04
ServerIp :
ServerHostname :
SourceContext :
ConnectorId :
Source : AGENT
EventId : AGENTINFO
InternalMessageId : 159562330013889
MessageId : <deae6b92a34d466cad83cf3b65085982@ICMXS04.MyInternal.ADDomain.biz>
Recipients : {UserC@ExternalDomain.co.kr, UserB@SiteB.de}
RecipientStatus : {}
TotalBytes : 354771
RecipientCount : 2
RelatedRecipientAddress :
Reference :
MessageSubject : FW: [HEC] REQUEST FOR YOUR COMPANY PROFILE
Sender : UserA@SiteA.ie
ReturnPath : UserA@SiteA.ie
Directionality : Originating
TenantId :
OriginalClientIp : 192.168.1.176
MessageInfo :
MessageLatency :
MessageLatencyType : None
EventData : {[AMA, SUM|v=0|action=|error=|atch=3], [AMA, EV|engine=M|v=0|sig=1.287.696.0|name=|file=],
[CompCost, |AMA=0|ETR=0], [DeliveryPriority, Normal], [ExternalOrgIdNotSetReason, ]}
PSComputerName : icmxs04.MyInternal.ADDomain.biz
RunspaceId : e7ce8656-d6f1-44e3-b104-c93a32a6f41a
PSShowComputerName : False
Timestamp : 2/25/2019 10:24:19 AM
ClientIp :
ClientHostname :
ServerIp :
ServerHostname : GCMXS04
SourceContext : ContentConversion
ConnectorId :
Source : ROUTING
EventId : TRANSFER
InternalMessageId : 159562330013890
MessageId : <deae6b92a34d466cad83cf3b65085982@ICMXS04.MyInternal.ADDomain.biz>
Recipients : {UserC@ExternalDomain.co.kr}
RecipientStatus : {}
TotalBytes : 459346
RecipientCount : 1
RelatedRecipientAddress :
Reference : {159562330013889}
MessageSubject : FW: [HEC] REQUEST FOR YOUR COMPANY PROFILE
Sender : UserA@SiteA.ie
ReturnPath : UserA@SiteA.ie
Directionality : Originating
TenantId :
OriginalClientIp :
MessageInfo :
MessageLatency :
MessageLatencyType : None
EventData : {[DeliveryPriority, Normal], [ExternalOrgIdNotSetReason, ]}
PSComputerName : icmxs04.MyInternal.ADDomain.biz
RunspaceId : e7ce8656-d6f1-44e3-b104-c93a32a6f41a
PSShowComputerName : False
Timestamp : 2/25/2019 10:24:19 AM
ClientIp : 192.168.0.249
ClientHostname : GCMXS04
ServerIp : 192.168.0.249
ServerHostname : GCMXS04.MyInternal.ADDomain.biz
SourceContext : 08D670BFCFBBCC9E;250 2.0.0 OK;ClientSubmitTime:2019-02-25T10:24:16.430Z
ConnectorId : Intra-Organization SMTP Send Connector
Source : SMTP
EventId : SEND
InternalMessageId : 159562330013889
MessageId : <deae6b92a34d466cad83cf3b65085982@ICMXS04.MyInternal.ADDomain.biz>
Recipients : {UserB@SiteB.de}
RecipientStatus : {250 2.1.5 Recipient OK}
TotalBytes : 354840
RecipientCount : 1
RelatedRecipientAddress :
Reference :
MessageSubject : FW: [HEC] REQUEST FOR YOUR COMPANY PROFILE
Sender : UserA@SiteA.ie
ReturnPath : UserA@SiteA.ie
Directionality : Originating
TenantId :
OriginalClientIp :
MessageInfo : 2019-02-25T10:24:16.445Z;LSRV=GCMXS04.MyInternal.ADDomain.biz:TOTAL=1
MessageLatency : 00:00:02.9530000
MessageLatencyType : LocalServer
EventData : {[E2ELatency, 3], [Microsoft.Exchange.Transport.MailRecipient.RequiredTlsAuthLevel,
Opportunistic], [DeliveryPriority, Normal], [ExternalOrgIdNotSetReason, ]}
PSComputerName : icmxs04.MyInternal.ADDomain.biz
RunspaceId : e7ce8656-d6f1-44e3-b104-c93a32a6f41a
PSShowComputerName : False
Timestamp : 2/25/2019 10:24:27 AM
ClientIp : 192.168.0.249
ClientHostname : GCMXS04
ServerIp : 173.194.79.27
ServerHostname : aspmx.l.google.com
SourceContext : 08D670BFCFBBCC9F
ConnectorId : Exch2010_Internet_Germany
Source : SMTP
EventId : FAIL
InternalMessageId : 159562330013890
MessageId : <deae6b92a34d466cad83cf3b65085982@ICMXS04.MyInternal.ADDomain.biz>
Recipients : {UserC@ExternalDomain.co.kr}
RecipientStatus : {[{LRT=};{LED=550-5.7.1 This message does not have authentication information or fails to
pass 550-5.7.1 authentication checks. To best protect our users from spam, the 550-5.7.1
message has been blocked. Please visit 550-5.7.1
https://support.google.com/mail/answer/81126#authentication for more 550 5.7.1 information.
n1-v6si827532ejh.212 - gsmtp};{FQDN=};{IP=}]}
TotalBytes : 459348
RecipientCount : 1
RelatedRecipientAddress :
Reference : {<f201ad6b-1018-4a36-977b-391ceb1b72cb@GCMXS04.MyInternal.ADDomain.biz>}
MessageSubject : FW: [HEC] REQUEST FOR YOUR COMPANY PROFILE
Sender : UserA@SiteA.ie
ReturnPath : UserA@SiteA.ie
Directionality : Originating
TenantId :
OriginalClientIp :
MessageInfo : 2019-02-25T10:24:16.445Z;SRV=ICMXS04.MyInternal.ADDomain.biz:TOTAL=0;SRV=GCMXS04.MyInternal.ADDomain.biz:TOTA
L=9|QDE=6|SMS=1
MessageLatency :
MessageLatencyType : None
EventData : {[E2ELatency, 11], [ExternalSendLatency, 3],
[Microsoft.Exchange.Transport.MailRecipient.RequiredTlsAuthLevel, Opportunistic],
[Microsoft.Exchange.Transport.MailRecipient.EffectiveTlsAuthLevel, EncryptionOnly],
[DeliveryPriority, Normal], [ExternalOrgIdNotSetReason, ]}
PSComputerName : icmxs04.MyInternal.ADDomain.biz
RunspaceId : e7ce8656-d6f1-44e3-b104-c93a32a6f41a
PSShowComputerName : False
Timestamp : 2/25/2019 10:24:19 AM
ClientIp :
ClientHostname : GCMXS04.MyInternal.ADDomain.biz
ServerIp :
ServerHostname : GCMXS04
SourceContext : 08D63C094B20D795;2019-02-25T10:24:19.210Z;ClientSubmitTime:2019-02-25T10:24:16.430Z
ConnectorId :
Source : STOREDRIVER
EventId : DELIVER
InternalMessageId : 159562330013889
MessageId : <deae6b92a34d466cad83cf3b65085982@ICMXS04.MyInternal.ADDomain.biz>
Recipients : {UserB@SiteB.de}
RecipientStatus : {}
TotalBytes : 354840
RecipientCount : 1
RelatedRecipientAddress :
Reference :
MessageSubject : FW: [HEC] REQUEST FOR YOUR COMPANY PROFILE
Sender : UserA@SiteA.ie
ReturnPath : UserA@SiteA.ie
Directionality : Originating
TenantId :
OriginalClientIp : 192.168.1.176
MessageInfo : 2019-02-25T10:24:16.445Z;SRV=ICMXS04.MyInternal.ADDomain.biz:TOTAL=0;SRV=ICMXS04.MyInternal.ADDomain.biz:TOTA
L=0;SRV=GCMXS04.MyInternal.ADDomain.biz:TOTAL=1;SRV=GCMXS04.MyInternal.ADDomain.biz:TOTAL=0
MessageLatency : 00:00:02.9530000
MessageLatencyType : EndToEnd
EventData : {[MailboxDatabaseName, MBXEppstein], [Mailboxes, 8b81034e-668d-4faa-888d-b1e6feb17997],
[E2ELatency, 3], [DeliveryPriority, Normal], [ExternalOrgIdNotSetReason, ]}