Windows 2008 AD + Exchange 2007 migration to 2016 - exchange-server

Question

Today, I'm facing a problem with one of my customers. In his infrastructure, there's a server, that's doing everything (literally). This is Small Business Server 2008 (not R2), with Exchange 2007 and SQL Server 2005.
Since the business isn't small anymore - the old server is completely overloaded and is not responsive anymore. That's why the customer asked me to set up new server, so the old one can be released from some its jobs.
I've bought new Dell PowerEdge R320 with Windows Server 2016 Std. Cool, huh? Nope. Server 2016 isn't compatible with anything on the old server and now I'm literally stucked between two servers.
I need to migrate at least AD Controller and Exchange server from the old machine to new one.
On the new machine - I've set up second domain controller and I have problem with Exchange migration.
Microsoft oficially states that the migration between Exch 2007 and 2016 can't be done because of incompatibility, that's why I need to use 2013 trial.
And my first question: what should I do first:
- migrate the exchange 2007 to 2013, then promote new server as main ad controller and turn off ad controller on the old one (sbs2008 can be only the master ad controller - it can't be set up as slave), or
- first promote new server as main AD controller, turn of ad on the old one and then migrate the exchange?
The second thing is that the Exchange 2016 won't even install in environment where Exch 2007 is running, so I need to remove 2007 completely and then migrate from 2013 trial to 2016. Can this be done on the same machnine?
Thank you in advance and best regards.
Tom.

Answer 1

first promote new server as main AD controller, turn of ad on the old one and then migrate the exchange
SBS Servers needs to hold the FSMO roles. If you migrate them away your SBS will at some point start to shutdown itself (21 days? not sure on the exact time). If you can migrate in this timeframe than you could migrate the FSMO roles before migrating the rest. As it doesn't matter which server holds the FSMO roles to migrate SBS to the new server(s), I would migrate the FSMO roles in the decommissioning process.
The second thing is that the Exchange 2016 won't even install in
environment where Exch 2007 is running, so I need to remove 2007
completely and then migrate from 2013 trial to 2016. Can this be done
on the same machine?
This is not supported and I'm assuming that the Exchange 2016 setup will throw an error message at the prerequisite check.
A few points to your attention:
Don't install Exchange Server on Active Directory Servers, this is not recommended/supported
since CU3 Exchange 2016 "needs" at least Server 2008 R2 SP1 Active Directory Infrastructure to be supported
To work with Exchange 2016 your clients need to be at least Outlook 2010
Here is (roughly) what I would do:
Install an Hypervisor (Hyper-V, ESXi, Xen whatever you like/can support)
Install at least three VMs with Server 2016 (one Active Directory, two Exchange, plus additional servers for role separation)
Migrate Active Directory to the new Active Directory Server
Migrate your Exchange Server to the Exchange 2013
Migrate everything else from the SBS (e. g. SQL, Files, etc.)
Decommission the SBS (e.g. move FSMO Roles, uninstall Exchange, AD demote, ...)
Migrate from Exchange 2013 to 2016
Decommission the Exchange 2013
Upgrade Forest and Domain Functional Levels
Depending on customer size and need for availability you could do a shared nothing migration and jump from 2007 to 2016 by:
Export all Mailboxes to PST
Delete all Mailboxes
Uninstall Exchange 2007 (eventually you need to manually edit the AD using ADSIEdit! Be sure to know what you are doing!)
Install Exchange 2016
Create new Mailboxes
Import the PST files
Normally you don't need to use ADSIEdit, but I have seen a few instances were not everything was removed by Exchange Setup.