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YOU ARE HERE: HOME / TUTORIALS / CONFIGURING OUTBOUND MAIL FLOW IN EXCHANGE SERVER 2013

Configuring Outbound Mail Flow in


Exchange Server 2013

MAY 4, 2013

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PAUL CUNNINGHAM

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Outbound mail flow in Exchange Server 2013 is managed with the use of Send Connectors.

Send Connectors are not configured by default when you first install Exchange Server 2013.
If the Exchange 2013 server is installed in an existing organization then other Send
Connectors may already exist that facilitate outbound mail flow. Otherwise, you will need to
create at least one Send Connector yourself.
Most organizations will be dealing with one of the following outbound email flow scenarios:
email sent directly over the internet to the recipients server
email sent to the internet via a smart host

Sending directly over the internet vs sending via a smart host


There are other scenarios as well, such as:
email sent outbound via an Edge Transport server
email sent directly to a partner organization using TLS encryption
An organization can have one, two, or several Send Connectors to provide the specific email
routing that they need.
For this article well focus on the first two scenarios, as they are the most common; sending
directly to the internet, and sending via a smart host. Well also cover testing and
troubleshooting a Send Connector, and some more advanced configuration options.

CONFIGURING OUTBOUND MAIL FLOW DIRECT


TO THE INTERNET
Configuring your Exchange 2013 organization to send means that your Exchange server will
look up the MX records for the recipients email address, and then use those MX records as
the IP address(es) to connect to via SMTP.
Looking up MX records means your server will be relying on DNS. If the servers TCP/IP
settings are configured for DNS servers inside your network that cant resolve external
names, then you can configure Exchange to use different DNS servers for external lookups.

To create the Send Connector for sending outbound email directly to the internet open the
Exchange Admin Center and navigate to Mail Flow -> Send Connectors.

Click the + button to create a new Send Connector.

Give the connector a name and set the type to Internet. Click Next to continue.

Leave the network settings set to MX record. If you needed to configure specific external
DNS servers you should also tick the box, but if your Exchange server can already resolve
external DNS names then that should not be required. Click Next to continue.

Click the + button to add a new address space. Specify the FQDN of * (the wildcard
character that effectively means anything). The cost can remain at the default setting of 1
if this is the only send connector for your organization. Click Save and then click Next to
continue.

Click the + button to add the source servers for the connector. These are the servers that
will be responsible for routing email out from your organization to the internet. Multiple
servers will provide redundancy for outbound mail flow. Click OK and then click Finish.

The send connector is now visible in the Exchange Admin Center.

For further configuration and tested steps refer to the last section of this article.

CONFIGURING OUTBOUND MAIL FLOW VIA A


SMART HOST
Configuring a Send Connector to send outbound internet email via a smart host is the same
process as above, with the following differences.
First, the network setting is configured to Route mail through smart hosts instead of MX
records. You must then click the + button to add at least one smart host name or IP address.
Multiple smart hosts are permitted and are recommended for redundancy.

When you choose to use a smart host you also get the option to configure authentication for
the Send Connector. This is only necessary if the smart host requires it. Many email security
servers/appliances or even hosted solutions will simply authenticate you based on your IP
address rather than require other credentials.

TESTING A NEW SEND CONNECTOR


The obvious way to test a new send connector is to send an email from inside the
organization to an external recipient.
When the message is received in the external mailbox you can then take the message
headers and use the MXToolbox header analyzer or the ExRCA Message Analyzer to inspect
the headers and confirm that the email passed through the source servers you were
expecting it to for that outbound route.

If the email does not arrive you can inspect the transport queues on your Exchange servers
for stuck email.
[PS] C:\>Get-TransportService | get-queue
Identity

DeliveryType Status MessageCount Velocity RiskLevel OutboundIPPool NextHopDomain

--------

------------ ------ ------------ -------- --------- -------------- -------------

E15MB1\22206

SmtpDeliv... Ready

Normal

mailbox database 1

E15MB1\Submission

Undefined

Ready

Normal

Submission

E15MB1\Shadow\22204

ShadowRed... Ready

Normal

e15mb3.exchange201

E15MB2\22750

SmtpDeliv... Ready

Normal

mailbox database 2

E15MB2\Submission

Undefined

Ready

Normal

Submission

E15MB2\Shadow\22748

ShadowRed... Ready

Normal

e15mb1.exchange201

E15MB3\Submission

Undefined

Ready

Normal

Submission

E15MB3\Shadow\16452

ShadowRed... Ready

Normal

e15mb1.exchange201

E15MB3\Shadow\16456

ShadowRed... Ready

Normal

e15mb2.exchange201

To look more closely at the messages stuck in a single queue you can use Get-Queue and

Get-Message together.
[PS] C:\>Get-Queue E15MB1\22206 | Get-Message | ft

If the properties of the stuck messages do not reveal the problem then another valuable
source of troubleshooting information is the protocol logs. For more tips refer to the
following article:
Troubleshooting Email Delivery with Exchange Server Protocol Logging

FURTHER CONFIGURATION OPTIONS FOR SEND


CONNECTORS
Some additional configuration options you can explore are:
Proxying email through Front End/Client Access Servers
Configuring protocol logging for Exchange 2013
Configuring outbound message size limits for Exchange 2013
Configuring the FQDN for HELO/EHLO on a send connector

FILED UNDER: TUTORIALS

TAGGED: EXCHANGE 2013, MAIL FLOW, SEND CONNECTOR, TRANSPORT

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ABOUT PAUL CUNNINGHAM


Paul is a Microsoft Exchange Server MVP and publisher of
Exchange Server Pro. He also holds several Microsoft
certifications including for Exchange Server 2007, 2010 and 2013.
Find Paul on Twitter, LinkedIn or Google+, or get in touch for consulting/support
engagements.

RELATED ARTICLES:

1. Exchange Server 2013 Mail Flow and Transport Services


2. How to Correctly Use Multiple Smart Hosts to Load Balance Outbound Email for
Exchange 2010
3. Restricting outbound email with Exchange Server 2007 Transport Rules

4. Route outbound email through the Exchange Server 2007 Hub Transport server
5. Configuring the Exchange Server 2007 Hub Transport Server

COMMENTS

Moses Kihumuro says


August 9, 2013 at 10:33 pm

This is a very helpful post. It was handy in guiding me on how to setup exchange to
use smarthosts.
Reply

Denny Eapen says


October 11, 2013 at 5:51 am

Hi Paul:
Good article.

Does it mean that emails CAN be sent to internet with only Mailbox Role and no
CAS?
Thanks
Denny
Reply

Paul Cunningham says


October 13, 2013 at 11:19 am

CAS is still a required role in an Exchange deployment.


Reply

Mor says
November 16, 2013 at 11:55 pm

I am a new IT engineer and learning Exchange server 2013.


To connect Exchange server 2013 to internet, how can we make it in safely ?

Please share your opinion.


Reply

Grant says
December 4, 2013 at 9:30 am

Is it possible via send connector or other means (rule perhaps) to send all mail
*from* a specific internal domain through a smarthost? For example, lets say we
have two divisions and each have their own domain joe@maindiv.com and
bob@subdiv.com. Subdiv requires a smarthost for regulatory compliance,
maindiv.com does not. Can we force outbound mail for subdiv.com through the
smarthost but not maindiv.com so we dont have to pay for compliance services?
Reply

Victor says
May 18, 2014 at 4:25 am

Have a look at this tool:


http://www.ivasoft.com/routebysender.shtml

Reply

Kyle Kennedy says


December 10, 2013 at 5:20 am

There is an option in the general tab of the send connector properties for Proxy
through client access server. I understand in a split role environment, this box
makes it work like 2010, ie, mail goes from mailbox to CAS and then sent out from
there. However, what is the proper setting when CAS and MB are on the same
server? Checked or unchecked?
Reply

Paul Cunningham says


December 11, 2013 at 11:14 pm

There is no proper setting. The option exists for specific scenarios that some
customers might have.
On multi-role servers it doesnt matter either way, in my opinion.

Reply

ajhstn says
February 22, 2014 at 4:08 pm

Hey all,
I am in the process of migrating from EX 2010 to EX 2013. I have an existing 2010
2x dag, 2x cas environment. I have built on new servers 1x 2013 cas, and 1x 2013
mb.
I have followed the step by step Exchange Server Deployment Assistant but cannot
see it talk of mail flow anywhere. I have a single send connector in the 2010 env. I
have various receive connectors. all https,http,smtp,imap and other
outlook,rpc,mapi traffic go through a Riverbed Stingray Traffic Manager. My send
connector routes email through a smart host.
I have created a exchange 2013 mailbox. I can send email from 2010 to 2013, but I
cannot send email from 2013 to 2010. Both farms are in the same domain, same
network. They are all hyperv vm guests in the same cluster.

The email that I try to send from the 2013 env to 2010 gets stuck in the 2013
Queue Viewer, its status is READY, it has no last error.
Can anyone help clear this up for me? I need exchange 2010 and 2013 to coexist for
a period of a few weeks, while I migrate all mailboxes, then after that I will close
down exchange 2010.
Thank you in advance.
Andrew
Reply

Paul Cunningham says


February 23, 2014 at 8:17 pm

You should begin by troubleshooting SMTP connectivity from 2013 -> 2010.
Try it with telnet. Check for antivirus or security products, or firewalls, or your
Riverbed device, that may be interfering with the connections.
Also look closer at the messages stuck in the queue. What is the last error? That
usually gives you some hints about what the problem may be. Misconfigured
Receive Connector permissions on the 2010 server is a example of where
things can go wrong too, eg http://support.microsoft.com/kb/979175

Reply

tricky says
July 12, 2014 at 5:47 am

Hello Paul, you have a nice blog!


Please give me advice:
I just installed only 2 multy role server 2013 in two different sites. Inbound mail
works fine, but I just try to create new one send connector in new site , and
outbound mail flow stop working for me. If i disabe new send connector (just create
it like post- internet- next- asterisk- next- my cas\mailbox in site 2 to scope)
Annnd my mail do not go to Internet, just qued. What I doing wrong?
Reply

burt340 says
August 7, 2014 at 3:58 am

Paul great article, is there a way to get exchange to ignore internal recipients (prestaged for a migration) and send route messages our through a send connector?
Reply

Paul Cunningham says


August 8, 2014 at 11:25 am

Sure. Apply forwarding on the mailbox.


Reply

Voffka says
September 12, 2014 at 6:21 pm

Hi, Paul. Thanks for your article, its amazing, as usual


the question is, like it was mentioned before,
Is it possible via send connector or other means (rule perhaps) to send all mail
*from* a specific internal domain through a smarthost? For example, lets say we

have two divisions and each have their own domain joe@maindiv.com and
bob@subdiv.com. Subdiv requires a smarthost for regulatory compliance,
maindiv.com does not. Can we force outbound mail for subdiv.com through the
smarthost but not maindiv.com so we dont have to pay for compliance services?
how to route mail thru a specific edge based on users primary domain ?
Reply

Victor says
December 15, 2014 at 10:24 pm

Google for RooteBySender tool.


Regards,
Victor
Reply

Mohan says
December 4, 2014 at 11:10 pm

Hi,
which server we need to mentioned in Configuring the FQDN for HELO/EHLO on
a send connector
Cas or mailbox ?
Reply

Paul Cunningham says


December 8, 2014 at 1:13 pm

Use whichever hostname you want to appear to the outside world, eg


smtp.domain.com, or just the hostname of the Mailbox server.
Reply

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ABOUT PAUL CUNNINGHAM

Paul is a Microsoft Exchange


Server MVP and publisher of
Exchange Server Pro. He also
holds several Microsoft certifications
including for Exchange Server 2007,
2010 and 2013. Find Paul on Twitter,
LinkedIn or Google+, or get in touch for
consulting/support engagements.

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