Migrating A Small Organization From Exchange 2010 To Exchange 2016 (Part 5)

2/5/2018 Migrating a small organization from Exchange 2010 to Exchange 2016 (Part 5) - TechGenix
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Migrating a small organization FEATURED PRODUCT
from Exchange 2010 to

Exchange 2016 (Part 5)
Steve Goodman 1  6 Views  9
POSTED ON MARCH 9, 2016
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(Part 6)
Introduction
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During the last part in this series we completed the post installation Get a free copy of
the new
configuration of Exchange Server 2016 and configured it as per our basic SolarWinds
design, then performed some basic tests to ensure it functions correctly. Permissions
Analyzer!
We’re now ready to update the mail routing to the Exchange 2016 server in
preparation for the migration. We’ll also integrate with an Office Online
Server as an optional step before migration to allow documents to be
previewed within Outlook Web App.
RECOMMENDED
Migrating Mail Routing Migrating

Public Folders
to Exchange
Updating Inbound Mail Routing 2013 (Part 2)
In the previous article, we tested to ensure that our Exchange 2016 server can Migrating a
small
receive mail and deliver it to Exchange 2010 users. By default, Exchange organization
from
Server 2016 is already configured to receive email from the Internet using Exchange 2010
Anonymous permissions on the default receive connector. to Exchange
2013 (Part 1)
If this hasn’t been changed from the defaults, update either firewall rules to Deploying
Exchange
direct traffic on SMTP port 25 to the Exchange 2016 server, or update your Server 2016
spam filter appliance to do so. (Part 1)
RECOMMENDED
Best and worst practices for Microsoft Exchange

TLS and SSL
FOLLOW US
After this change has been applied ensure that inbound mail flow is not
interrupted before moving on to migrating outbound mail flow.  
Updating Outbound Mail Routing

With incoming mail now flowing through Exchange 2016, our next step is to
make the changes required to allow and then reconfigure Exchange Server
2016 to be responsible for outbound mail flow rather than via the Exchange
2010 server.
In our example environment our mail flow is direct to the Internet, but in
your organization you might use a spam filter appliance. Therefore, make
sure if you use a smart host for relay, ensure the IP address of the new
Exchange 2016 server is added as a server allowed to relay outbound  9 COMMENTS  SHARE
messages.
Likewise, if you email direct to recipients then ensure the Firewall rules
allow the Exchange 2016 server IP address to initiate connections to Internet
hosts on TCP port 25 without tampering (such as SMTP Fixup).
After ensuring that the Exchange 2016 server is allowed to relay outbound
mail, we are ready to update the Send Connector. To perform this step, open
the Exchange Admin Center and navigate to Mail Flow and then choose Send
Connectors. You should see the Send Connector used for outbound mail flow
within the list:
Figure 1: Locating the primary Send Connector for outbound email
Open the properties for the Send Connector used for outbound mail flow.
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G E T E X C L U S I V E U P D AT E S
Navigate to the Scoping tab and locate the Source server section. The
Exchange 2010 server should be listed. Choose Add (+) and select the
Exchange 2016 server, then select the Exchange 2010 and choose Remove (-);
leaving only the Exchange 2016 server within the server list:

Figure 2: Updating send connector settings
After verifying both the server IP address is listed as able to relay, and that
the correct Exchange 2016 server has been selected, choose Save to apply the
configuration.
As with updating inbound mail routing, ensure you test outbound mail flow is
unaffected before continuing.
Installing Of ce Online Server

Optionally, before migrating mailboxes we can install Office Online Server.
At the time of writing, this is still in preview and is expected to reach general
availability (GA) around the same time SharePoint Server 2016 is launched.
The Office Online Server is required for viewing and editing attachments
within a web browser, so for our small organization we will walk through the
installation of a single server farm. For larger organizations, high availability
may be required.
Installation of Of ce Online Server

The current version of Office Online Server, the preview version, can be
downloaded from this Microsoft link.
This must be installed on a standalone Windows 2012 R2 virtual machine or

server. Before commencing the install we must also install a number of pre-
requisites. First install the Visual Studio 2015 runtime from this link.
Next, install the .Net Framework 4.5.2, then install all available Windows
Updates.
Finally, before commencing the installation, use the following PowerShell  9 COMMENTS  SHARE
script to install all required pre-requisites, as shown below:
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Install-WindowsFeature
 Web-Server,
 Web-Mgmt-Tools, 
Console, Web-WebServer, Web-Common-Http, Web-Default-Doc, Web-

Static-Content, Web-Performance, Web-Stat-Compression, Web-Dyn-
Compression, Web-Security, Web-Filtering, Web-Windows-Auth, Web-
App-Dev, Web-Net-Ext45, Web-Asp-Net45, Web-ISAPI-Ext, Web-ISAPI-
Filter, Web-Includes, InkandHandwritingServices
Figure 3: Installing OOS server pre-requisites
After installation of pre-requisites, perform a re-boot.
Next, mount the ISO image downloaded for installing Office Online Server
and then start setup. For our installation, we’ll leave all defaults as-is. In the
preview you will note that the version of Office Online Server is 2013. This
is expected:
Figure 4: Installing Office Online Server.
Con guration of Of ce Online

Server
After installation completes, Office Online Server will not be available for  9 COMMENTS  SHARE
use. To make it available for use with Exchange Server 2016 we must install
a new Office Online Farm.
Before we do that, we’ll need to install a valid SSL certificate and configure a
DNS name.
The standard naming for Office Online Server is oos.domain.com. We will

choose to use oos.stevieg.org for both the internal and external URLs for our
simple farm.
We’ll use the Manage Computer Certificates management snap-in to import

the SSL certificate and check the certificate Friendly Name. Search in the
Windows 2012 R2 Start Menu, then launch the snap-in:
Figure 5: Locating Computer Certificates
You should see Certificate – Local Computer launch. Navigate to Personal

and right-click Certificates. Choose All Tasks>Import… and import your
certificate.
Figure 6: Importing an existing SSL certificate
In our example we’ve imported an example Wildcard certificate. We’ll

navigate to Certificates and record its Friendly Name from the list.
Figure 7: Checking the

Migrating Friendly
a small Name of the SSL
organization certificate
from Exchange 2010 to Exchange 2016 (Part 5)
You’ll note from the command below that we specifically need to enable  9 COMMENTS  SHARE
editing of documents when creating the farm. This is dependent on whether

or not you have appropriate Office licensing. We are choosing to enable it in

theSECTIONS
examplebelow:
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New-Of ceWebAppsFarm -InternalURL "https://<OOS FQDN>" -

ExternalURL "https://<OOS FQDN>" " -Certi cateName "<Certi cate
Name>" -EditingEnabled
Figure 8: Creating a new Office Online Server Farm
Con guration of Exchange 2016

To ensure that Exchange Server 2016 can utilize our new Office Online
Server farm we must configure the discovery endpoint using PowerShell.
This can be configured at the Mailbox server level, or the organization level.
It is useful to configure at the mailbox level if you need to maintain co-
existence with Exchange 2013.
As we are upgrading from Exchange 2010, we can simply configure the

endpoint at the organizational level with the Set-OrganizationConfig cmdlet
and then restart the OWA app pool on our single server, as shown below:
Set-OrganizationCon g -WacDiscoveryEndpoint https://<OOS

FQDN>/hosting/discovery
Restart-WebAppPool MsExchangeOwaAppPool

Figure 9: Configuring Exchange 2016 to use the Office Online Server
Testing Of ce Online Server with

Exchange 2016
Finally, we’ll need to make sure that document viewing and editing works as
expected. If all is configured correctly, then viewing an email with an
attachment should present the View option against an attachment:
Figure 10: Checking integration of OOS
If you don’t see the option it may simply be that after making the
Organization configuration change, Active Directory had not replicated
before re-starting the OWA app pool and attempting access.
When you see the view option, simply select it to switch to view mode. If
you’ve also enabled Editing in the Office Online Farm, you’ll see the Edit
and reply option as well.
Figure 11: Viewing attachments using OOS

By selecting Edit and reply, you will be able to compose a reply and edit the  9 COMMENTS  SHARE
document before sending. If the configuration is correct then you should see
the full Office Online in editing mode displayed:
Figure 12: Editing attachments using OOS
Summary
In this penultimate part in the series we’ve migrated mail routing across from
Exchange 2010 to Exchange 2016, and we’ve installed Office Online Server
(if required) to allow viewing and editing of attachments in Outlook Web
App. In the final part of this series we will migrate mailboxes, then
decommission Exchange Server 2010.
If you would like to read the other parts in this article series please go to:

(Part 1)
(Part 2)
(Part 3)
(Part 4)
(Part 6)
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TECHGENIX » MS EXCHANGE SERVER » DEPLOYMENT & MIGRATION » MIGRATING A SMALL

ORGANIZATION FROM EXCHANGE 2010 TO EXCHANGE 2016 (PART 5)
AUTHOR
Steve Goodman
Steve is a 5 times recipient of the MVP (Microsoft’s Most

Valuable Professional) award from Microsoft, is a
regular international conference speaker, podcast host,
regular blogger, plus he is the author of a number of
popular Exchange books. Steve is Head of Messaging
and UC at top Of ce 365 partner Content and Code,
responsible for their Exchange and Skype for Business
offerings. Steve has worked on a vast number of
Exchange and Of ce 365 projects across customers
large and small, often with complex requirements and
loves to share his expertise.
9 COMMENTS
andrew April 4, 2017 at 5:04 am R E P L Y
hi Part 6 is missing.

Akos Vajda April 4, 2017 at 8:32 am R E P L Y

Hi Andrew,
You can find it here:
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exchange-2010-exchange-2016-part6/
Justin June 2, 2017 at 2:37 pm R E P L Y
Having problem with send connector. One thing I notice is

2016 exchange only shows mailbox role, while 2010 show
mailbox, clientaccess, hubtransport.
steve E August 10, 2017 at 10:37 am R E P L Y
do i have to remove the exchange 2010 after selecting the

send and receive conns ? or can they both stay until i finish
moving mailboxes ??
Steve Goodman August 10, 2017 at 12:37 pm R E P L Y
Hi Steve,
No, you can keep Exchange 2010 around for as long as you
desire.
Steve
steve E August 10, 2017 at 12:44 pm R E P L Y
thank you !
just one more thing…does this look right,,i notice the

new server only says mailbox under roles,,, not client
access , hub transport like the 2010 does,,,is this right? o
am i missing something, we dont use public folders…
Steve Goodman August 10, 2017 at 1:12 pm R E P L Y
Hi, that’s expected. Exchange 2016 combines those roles

together and just calls it the Mailbox role.
awesome,,,i guess i did it right !!! Thank You for all you
help !!
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SECTIONS  TECH NEWS  TUTORIALS REVIEWS NEWSLETTERS VIDEOS ABOUT  

Migrating a small organization FEATURED PRODUCT

from Exchange 2010 to

POSTED ON MARCH 9, 2016

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