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Hybrid Mode with Office 365 not routing mail to Cloud

Posted on 2016-09-15
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Last Modified: 2016-09-24
For this discussion, let's say my domain is mydomain.com.

I have setup a hybrid mode environment between my on-premise Exchange 2010 server and our Office 365 cloud environment. I performed a remote move to move a single mailbox to the cloud for testing. The move was successful except that, while this account can send email out, no email can be received by it. We received a bounced back message from another SMTP server saying that email could not be relayed.

Checking into the Exchange Message tracking on my on-premise, I see that the messages destined for that user are successfully received but then fail to send out because they are attempting to be sent to the host "www.mydomain.com" (see attached image). Obviously, they should be being sent to Office 365's SMTP servers for our domain. I also noticed that Exchange seems to be using the wrong send connector when attempting to send out to Office 365. Instead of using the "Outbound to office 365" connector, it's using my "Default" one. Can someone please help? I am also working with Microsoft on this, but I don't get the impression that the people I am working with really understand what's going on and I end up trying a lot of unrelated things to try and fix it.

Any help would be greatly appreciated. Thank you.

Message Tracking screen
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by:Akhater
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how did you do your hybrid configuration ? did you use the wizard of exchange 2010 ? or did you download the new one ? because the one built in in 2010 is no longer supported maybe it did a wrong configuration somehow
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by:Akhater
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by:medium_grade
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Akhater,

I downloaded the one from Microsoft.
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by:Akhater
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ok good to know

is the mailbox you have migrated on the same SMTP domain as your exchange server? and who is 72.47.228.65 is it your server or someone on the net ?
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by:medium_grade
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That's the server it keeps trying to relay through which is the wrong one. That's actually our website host. The whole problem is that it keeps trying to use that host instead of our Office 365 SMTP servers.
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by:Akhater
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get-sendconnector "Outbound to office 365" | fl

can you give me the resutls
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by:medium_grade
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Here are the results. I have replaced our actual domain with "mydomain"

AddressSpaces                : {smtp:mydomainLA.mail.onmicrosoft.com;1}
AuthenticationCredential     :
Comment                      :
ConnectedDomains             : {}
ConnectionInactivityTimeOut  : 00:10:00
DNSRoutingEnabled            : False
DomainSecureEnabled          : False
Enabled                      : True
ErrorPolicies                : DowngradeAuthFailures
ForceHELO                    : False
Fqdn                         : webmail.mydomain.org
HomeMTA                      : Microsoft MTA
HomeMtaServerId              : MX-01
Identity                     : Outbound to Office 365
IgnoreSTARTTLS               : False
IsScopedConnector            : False
IsSmtpConnector              : True
LinkedReceiveConnector       :
MaxMessageSize               : 10 MB (10,485,760 bytes)
Name                         : Outbound to Office 365
Port                         : 25
ProtocolLoggingLevel         : None
RequireOorg                  : False
RequireTLS                   : True
SmartHostAuthMechanism       : None
SmartHosts                   : {mydomainla.mail.protection.outlook.com}
SmartHostsString             : mydomainla.mail.protection.outlook.com
SmtpMaxMessagesPerConnection : 20
SourceIPAddress              : 0.0.0.0
SourceRoutingGroup           : Exchange Routing Group (DWBGZMFD01QNBJR)
SourceTransportServers       : {MX-01}
TlsAuthLevel                 : DomainValidation
TlsDomain                    : mail.protection.outlook.com
UseExternalDNSServersEnabled : False

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by:Akhater
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ok everything seems fine here

what about

get-recipient migrateduser | fl
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by:medium_grade
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Here ya' go:


RunspaceId                         : 81148bc6-b1db-4611-ba71-53472b0a82d3
Alias                              : JEllick
ArchiveGuid                        : 00000000-0000-0000-0000-000000000000
AuthenticationType                 :
City                               :
Notes                              :
Company                            :
CountryOrRegion                    :
PostalCode                         :
CustomAttribute1                   :
CustomAttribute2                   :
CustomAttribute3                   :
CustomAttribute4                   :
CustomAttribute5                   :
CustomAttribute6                   :
CustomAttribute7                   :
CustomAttribute8                   :
CustomAttribute9                   :
CustomAttribute10                  :
CustomAttribute11                  :
CustomAttribute12                  :
CustomAttribute13                  :
CustomAttribute14                  :
CustomAttribute15                  :
ExtensionCustomAttribute1          : {}
ExtensionCustomAttribute2          : {}
ExtensionCustomAttribute3          : {}
ExtensionCustomAttribute4          : {}
ExtensionCustomAttribute5          : {}
Database                           :
ArchiveDatabase                    :
DatabaseName                       :
Department                         :
ExternalDirectoryObjectId          :
ManagedFolderMailboxPolicy         :
EmailAddresses                     : {x500:/o=ExchangeLabs/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Recipi
                                     ents/cn=bb484bb2eeba4a96aedd2881c7625e40-Joe Ellick, X500:/o=My Domain Maternity Ho
                                     me/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Recipients/cn=Joe Ellick0
                                     b5, smtp:JEllick@mydomainLA.mail.onmicrosoft.com, X400:C=us;A= ;P=My Domain Materni;
                                     O=Exchange;S=Ellick;G=Joe;, SMTP:JEllick@mydomain.org}
ExpansionServer                    :
ExternalEmailAddress               : SMTP:JEllick@mydomain.org
DisplayName                        : Joe Ellick
FirstName                          : Joe
HiddenFromAddressListsEnabled      : False
EmailAddressPolicyEnabled          : True
LastName                           : Ellick
ResourceType                       :
ManagedBy                          : {}
Manager                            :
ActiveSyncMailboxPolicy            : Default
ActiveSyncMailboxPolicyIsDefaulted : False
Name                               : Joe Ellick
Office                             :
ObjectCategory                     : mydomain.ca.org/Configuration/Schema/Person
OrganizationalUnit                 : mydomain.ca.org/mydomain/Active Users/Occidental
Phone                              :
PoliciesIncluded                   : {194051b5-3f5f-4856-bf36-d52403fcddf4, {26491cfc-9e50-4857-861b-0cb8df22b5d7}}
PoliciesExcluded                   : {}
PrimarySmtpAddress                 : JEllick@mydomain.org
RecipientType                      : MailUser
RecipientTypeDetails               : RemoteUserMailbox
SamAccountName                     : JEllick
ServerLegacyDN                     :
ServerName                         :
StateOrProvince                    :
StorageGroupName                   :
Title                              :
UMEnabled                          : False
UMMailboxPolicy                    :
UMRecipientDialPlanId              :
WindowsLiveID                      :
HasActiveSyncDevicePartnership     : True
AddressListMembership              : {\Default Global Address List}
OwaMailboxPolicy                   :
AddressBookPolicy                  :
SharingPolicy                      :
MailboxMoveTargetMDB               :
MailboxMoveSourceMDB               :
MailboxMoveFlags                   : None
MailboxMoveRemoteHostName          :
MailboxMoveBatchName               :
MailboxMoveStatus                  : None
IsValidSecurityPrincipal           : False
RetentionPolicy                    :
LitigationHoldEnabled              : False
Capabilities                       : {}
ArchiveState                       : None
SKUAssigned                        : False
WhenMailboxCreated                 : 7/29/2015 8:41:05 AM
UsageLocation                      :
ExchangeVersion                    : 0.10 (14.0.100.0)
DistinguishedName                  : CN=Joe Ellick,OU=Occidental,OU=Active Users,OU=mydomain,DC=mydomain,DC=ca,DC=org
Identity                           : mydomain.ca.org/mydomain/Active Users/Occidental/Joe Ellick
Guid                               : e22ac6ae-c88c-4df8-94fd-6168802ae881
ObjectClass                        : {top, person, organizationalPerson, user}
WhenChanged                        : 9/11/2016 5:17:17 PM
WhenCreated                        : 7/29/2015 8:41:06 AM
WhenChangedUTC                     : 9/12/2016 12:17:17 AM
WhenCreatedUTC                     : 7/29/2015 3:41:06 PM
OrganizationId                     :
OriginatingServer                  : occ-dc1.mydomain.ca.org
IsValid                            : True

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by:Akhater
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From what you sent me

ExternalEmailAddress               : SMTP:JEllick@mydomain.org

this is wront it should be JEllick@mydomainLA.mail.onmicrosoft.com

notice i'm talking about the ExternalEmailAdress not the PrimarySMTPAddress

I'm surprised how you where able to migrate it in the first place (unless it is a mistake in cleaning the output)
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by:medium_grade
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Nope. That's it. So, how do I change this?
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by:Akhater
Akhater earned 500 total points
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Set-MailUser JEllick -ExternalEmailAddress JEllick@mydomainLA.mail.onmicrosoft.com

but you need to make sure of his @mydomainLA.mail.onmicrosoft.com in the office 365 portal first
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by:Akhater
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Set-MailUser JEllick -ExternalEmailAddress JEllick@mydomainLA.mail.onmicrosoft.com

but you need to make sure of his @mydomainLA.mail.onmicrosoft.com in the office 365 portal first
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medium_grade earned 0 total points
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Weird. Doesn't seem to recognize. When I run:

get-recipient jellick@mydomain.org | fl

I get output. When I run:

Set-MailUser JEllick -ExternalEmailAddress jellick@MyDomain.mail.onmicrosoft.com

I get the error "The operation couldn't be performed because object 'JEllick' couldn't be found on 'occ-dc1.mydomain.ca.org'" What am I doing wrong?
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by:Akhater
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Try it from the interface, it should be in under contacts
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by:Akhater
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What is the output of get-mailuser jellick@mydomain.org
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by:medium_grade
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Arrrg! It sends to Office 365 now, but now THEY'RE telling me the user jellick@mydomain.org does not exist! I see the account is present, there is a mailbox and the address is correct too!!!
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by:Akhater
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Open exchange poweshell don't connect to office 365 and try again

Get-mailuser migrateduser
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Author Comment

by:medium_grade
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you mean get-recipient jellick@mydomain.org | fl ??
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RunspaceId                         : 81148bc6-b1db-4611-ba71-53472b0a82d3
Alias                              : JEllick
ArchiveGuid                        : 00000000-0000-0000-0000-000000000000
AuthenticationType                 :
City                               :
Notes                              :
Company                            :
CountryOrRegion                    :
PostalCode                         :
CustomAttribute1                   :
CustomAttribute2                   :
CustomAttribute3                   :
CustomAttribute4                   :
CustomAttribute5                   :
CustomAttribute6                   :
CustomAttribute7                   :
CustomAttribute8                   :
CustomAttribute9                   :
CustomAttribute10                  :
CustomAttribute11                  :
CustomAttribute12                  :
CustomAttribute13                  :
CustomAttribute14                  :
CustomAttribute15                  :
ExtensionCustomAttribute1          : {}
ExtensionCustomAttribute2          : {}
ExtensionCustomAttribute3          : {}
ExtensionCustomAttribute4          : {}
ExtensionCustomAttribute5          : {}
Database                           :
ArchiveDatabase                    :
DatabaseName                       :
Department                         :
ExternalDirectoryObjectId          :
ManagedFolderMailboxPolicy         :
EmailAddresses                     : {x500:/o=ExchangeLabs/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Recipi
                                     ents/cn=bb484bb2eeba4a96aedd2881c7625e40-Joe Ellick, X500:/o=My Domain Maternity Ho
                                     me/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Recipients/cn=Joe Ellick0
                                     b5, smtp:JEllick@mydomainLA.mail.onmicrosoft.com, X400:C=us;A= ;P=My Domain Materni;
                                     O=Exchange;S=Ellick;G=Joe;, SMTP:JEllick@mydomain.org}
ExpansionServer                    :
ExternalEmailAddress               : SMTP:JEllick@mydomainLA.mail.onmicrosoft.com
DisplayName                        : Joe Ellick
FirstName                          : Joe
HiddenFromAddressListsEnabled      : False
EmailAddressPolicyEnabled          : False
LastName                           : Ellick
ResourceType                       :
ManagedBy                          : {}
Manager                            :
ActiveSyncMailboxPolicy            : Default
ActiveSyncMailboxPolicyIsDefaulted : False
Name                               : Joe Ellick
Office                             :
ObjectCategory                     : mydomain.ca.org/Configuration/Schema/Person
OrganizationalUnit                 : mydomain.ca.org/mydomain/Active Users/Occidental
Phone                              :
PoliciesIncluded                   : {}
PoliciesExcluded                   : {{26491cfc-9e50-4857-861b-0cb8df22b5d7}}
PrimarySmtpAddress                 : JEllick@mydomain.org
RecipientType                      : MailUser
RecipientTypeDetails               : RemoteUserMailbox
SamAccountName                     : JEllick
ServerLegacyDN                     :
ServerName                         :
StateOrProvince                    :
StorageGroupName                   :
Title                              :
UMEnabled                          : False
UMMailboxPolicy                    :
UMRecipientDialPlanId              :
WindowsLiveID                      :
HasActiveSyncDevicePartnership     : True
AddressListMembership              : {\Default Global Address List}
OwaMailboxPolicy                   :
AddressBookPolicy                  :
SharingPolicy                      :
MailboxMoveTargetMDB               :
MailboxMoveSourceMDB               :
MailboxMoveFlags                   : None
MailboxMoveRemoteHostName          :
MailboxMoveBatchName               :
MailboxMoveStatus                  : None
IsValidSecurityPrincipal           : False
RetentionPolicy                    :
LitigationHoldEnabled              : False
Capabilities                       : {}
ArchiveState                       : None
SKUAssigned                        : False
WhenMailboxCreated                 : 7/29/2015 8:41:05 AM
UsageLocation                      :
ExchangeVersion                    : 0.10 (14.0.100.0)
DistinguishedName                  : CN=Joe Ellick,OU=Occidental,OU=Active Users,OU=mydomain,DC=mydomain,DC=ca,DC=org
Identity                           : mydomain.ca.org/mydomain/Active Users/Occidental/Joe Ellick
Guid                               : e22ac6ae-c88c-4df8-94fd-6168802ae881
ObjectClass                        : {top, person, organizationalPerson, user}
WhenChanged                        : 9/15/2016 2:30:50 PM
WhenCreated                        : 7/29/2015 8:41:06 AM
WhenChangedUTC                     : 9/15/2016 9:30:50 PM
WhenCreatedUTC                     : 7/29/2015 3:41:06 PM
OrganizationId                     :
OriginatingServer                  : occ-dc1.mydomain.ca.org
IsValid                            : True

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Expert Comment

by:Akhater
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The same but use get-mailuser instead
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Author Comment

by:medium_grade
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When I do that "The operation couldn't be performed because object 'jellick@mydomain.org' couldn't be found on 'occ-dc1.mydomain.ca.org'"
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by:Akhater
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in your second output the email address is correct !!!!! what did you change ? how did you get that output

also please run
Get-RemoteMailbox | fl RemoteRoutingAddress

what is the reply ? if it is the correct one (onmicrosoft.com) try sending another email
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by:medium_grade
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I was able to set the External email address in the contacts like you told me.

I ran the command:

RemoteRoutingAddress : SMTP:JEllick@MyDomain.mail.onmicrosoft.com
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by:Akhater
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Try sending an email now
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Author Comment

by:medium_grade
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Still not working. Office 365 says the address is not recognized but I see the mailbox there!
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by:Akhater
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So it left your server and reached office 365?

What is the error message exactly
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Author Comment

by:medium_grade
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Your message to JEllick@mydomain.org couldn't be delivered.
JEllick wasn't found at mydomain.org.

But I KNOW it's there! I can send an email from jellick@mydomain.org in Office 365, but I get this message when I try to reply to it!
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by:Akhater
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I'm sorry to insist but

1. you are not seeing the unable to relay message anymore ? meaning that the routing is correct now ? is it using the correct connector ?

2. who generated this message ? in the full NDR you have the generating server

thanks
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Author Comment

by:medium_grade
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1. Yes, I am NOT seeing that same message anymore.

2. The message was generated by Office 365.

Which is frustrating because I can now send an email from jellick to myself, but when I reply to it, Office 365 says it's invalid.
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by:Akhater
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Would you send me the full correct email by private message so I can try some test?

If not do you know how to send an email by telnet? If yes please try to telnet to office 365 directly from your exchange and send an email
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by:Akhater
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I sent you an email thru telnet and it told me mailed queued for delivery (you might receive it in your inbox or maybe not if antispam stopped it) which means that the email is valid on the cloud

can you try to send a brand new email to this address and not reply to an exiting one ? and do another test send an email from an external recipient (Gmail / Hotmail) to that email directly
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by:Akhater
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I just got an NDR back regarding the email I sent to you and it came back from Office 365 that means,  as you said before, that the mail routing issue was solved emails are now reaching Office 365 however it is stating that the email address does not exist !

More Info for Email Admins
Status code: 550 5.1.10

This error occurs because the sender sent a message to an email address hosted by Office 365 but the address is incorrect or doesn't exist at the destination domain. The error is reported by the recipient domain's email server, but most often it must be fixed by the person who sent the message. If the steps in the How to Fix It section above don't fix the problem, and you're the email admin for the recipient, try one or more of the following:

The email address exists and is correct - Confirm that the recipient address exists, is correct, and is accepting messages.

Synchronize your directories - If you have a hybrid environment and are using directory synchronization make sure the recipient's email address is synced correctly in both Office 365 and in your on-premises directory.

Errant forwarding rule - Check for forwarding rules that aren't behaving as expected. Forwarding can be set up by an admin via mail flow rules or mailbox forwarding address settings, or by the recipient via the Inbox Rules feature.

Recipient has a valid license - Make sure the recipient has an Office 365 license assigned to them. The recipient's email admin can use the Office 365 admin center to assign a license (Users > Active Users > select the recipient > Assigned License > Edit).

Mail flow settings and MX records are not correct - Misconfigured mail flow or MX record settings can cause this error. Check your Office 365 mail flow settings to make sure your domain and any mail flow connectors are set up correctly. Also, work with your domain registrar to make sure the MX records for your domain are configured correctly.

can you please check and confirm the user's email address and the license ?
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by:Akhater
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can you please also confirm the remoterouting address is @MyDomainLA.onmicrosoft.com and not @mydomain.onmicrosoft.com ?
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by:medium_grade
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Finally got it, I believe!

I had gotten it so that I can send email to jellick@mydomainla.onmicrosoft.com both internally and externally. However, the address space for the outbound connector was mydomainla.mail.onmicrosoft.com. I simply added  to the outbound connector address space, then modified the contact for the user to be "jellick@mydomainla.onmicrosoft.com" (took the "mail" part out), reset the transport service and... STILL SAID DNS QUERY FAILED! Then, I set the outbound connector to use External DNS for lookups and the emails started going through!!! I have some more testing to do, but I would not have gotten this far without you. Thank you! Thank you! Thank you!
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by:Akhater
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Let me know if I can help in any way
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Author Closing Comment

by:medium_grade
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Only guy who helped.
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