SBS 2008 w/ Exchange to Windows Server 2016

[Taylor Oberst]

We have an old server and software and are currently looking to get everything upgraded. 

Right now we have SBS 2008 (not R2) w/ Exchange and Microsoft Office Suite 2007 and would like to upgrade to Windows Server 2016 w/ Exchange and Office 365 Business Premium.

There are a few things I need to know. 

1. Does Server 2016 include Exchange with it like SBS did, or does it come with the 365 suite, or is this something that needs installed separately, and if so, is there an additional cost?  We don't want cloud services and want to keep it on our local server.
2. I would prefer to use Sever 2016 in Essential mode, but I've read that Exchange will not work with this, so I wanted to make sure before I go with Server Standard.
3. Are there instructions on migrating from SBS 2008 server to 2016 server?  From what I can read online from Microsoft, all the instructions are incorrect and people have wasted many hours following them.

Thanks for any insight and help.

[#2]

Something here may help.

https://docs.microsoft.com/en-us/windows-server-essentials/migrate/migrate-windows-small-business-se...

or also ask for more help in dedicated forum here.

https://social.technet.microsoft.com/Forums/windowsserver/en-US/home?forum=ws16essentials

[#3]

Hello Taylor,

You may want to have a look at How to migrate from SBS 2008 to Windows Server 2016 (Essentials) and for the Exchange part you need to migrate first to Exchange Server 2013 How to migrate Exchange Server 2007 from SBS 2008 to a new Exchange Server 2013 on Windows Server 20.... The next hop will be Exchange Server 2016 and that is described in How to migrate Exchange Server 2013 to Exchange Server 2016 in a SBS migration scenario.

1. Remark: Outlook 2007 from your Office suite is NOT compatible with Exchange Server 2016.
2. Remark: Windows Server Essentials 2016 or Windows Server 2016 + Essentials Experience role works very well with a separate Exchange Server 2016. As a matter of fact Exchange Server 2016 can be integrated in the Essentials Dashboard and that will give you a SBS 2008/2011 Dashboard look and feel. I like it!

Oh yes, I would virtualize all of this. Just one beefy Hyper-V Host (the free one from Try Active Microsoft Hyper-V Server 2016 | Microsoft Evaluation Center) and use How to install and configure Microsoft Hyper-V Server 2016 for installation. Once the Hyper-V Host is ready you can add as many Virtual Machines as you want on the free version but you need in your scenario only two.

The end result will be a Windows Server 2016 that is your DC and another Windows Server 2016 with Exchange on it. Installing Exchange Server on a DC is no longer supported and though technically possible I would never implement it because it is a recipe for disaster.

The above scenarios are 100% success and if you have issues I will fix them for you.

---

Mariëtte Knap
www.server-essentials.com | Linkedin | Migrations done the easy way

Please remember to mark the replies as answers if they help and unmark them if they provide no help.

[#4]

Hello Taylor,

You may want to have a look at How to migrate from SBS 2008 to Windows Server 2016 (Essentials) and for the Exchange part you need to migrate first to Exchange Server 2013 How to migrate Exchange Server 2007 from SBS 2008 to a new Exchange Server 2013 on Windows Server 20.... The next hop will be Exchange Server 2016 and that is described in How to migrate Exchange Server 2013 to Exchange Server 2016 in a SBS migration scenario.

1. Remark: Outlook 2007 from your Office suite is NOT compatible with Exchange Server 2016.
2. Remark: Windows Server Essentials 2016 or Windows Server 2016 + Essentials Experience role works very well with a separate Exchange Server 2016. As a matter of fact Exchange Server 2016 can be integrated in the Essentials Dashboard and that will give you a SBS 2008/2011 Dashboard look and feel. I like it!

Oh yes, I would virtualize all of this. Just one beefy Hyper-V Host (the free one from Try Active Microsoft Hyper-V Server 2016 | Microsoft Evaluation Center) and use How to install and configure Microsoft Hyper-V Server 2016 for installation. Once the Hyper-V Host is ready you can add as many Virtual Machines as you want on the free version but you need in your scenario only two.

The end result will be a Windows Server 2016 that is your DC and another Windows Server 2016 with Exchange on it. Installing Exchange Server on a DC is no longer supported and though technically possible I would never implement it because it is a recipe for disaster.

The above scenarios are 100% success and if you have issues I will fix them for you.

---

Mariëtte Knap
www.server-essentials.com | Linkedin | Migrations done the easy way

Please remember to mark the replies as answers if they help and unmark them if they provide no help.