SBS 2011 Migration

We are upgrading our SBS 2011 to Server 2016, we are migrating both domain and exchange server. After going through some articles on web we have planned to do migration to 2 servers one for domain and dhcp and second for MS Exchange 2016. Our questions are

1. which server should we migrate over first.
2. when we migrate exchange do we require to do reconnections on the all desktops or the outlook would pick it up itself, we have outlook 2010 - 16
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P VStorage & Virtualization  ConsultantCommented:

Build Server 2016 join to existing domain as member server, point DNS to existing SBS server.

Build Second Server 2016 same as above, install Exchange 2016

Connect Exchange 2016 to existing Exchange 2010 via connector.

Test migrating one mailbox and test mail flow for this mailbox. If good proceed migrating all mailboxes

Once all mailboxes are migrated, proceed with final steps of Exchange migration resulting in the shutdown of Exchange 2010 on existing SBS server.

Setup DHCP on Server 2016 that will become DC

Do data migration to new 2016 server that will become DC

Promote server 2016 that will become DC to domain controller

Move FSMO roles from SBS server to new server 2016 that is to become DC

Shutdown SBS server and test environment.
Aussy99Author Commented:
Thanks for the helpful steps.

would the computers with win xp or windows NT work with new domain level in server 2016?

Also do we have to reconnect the desktops with the new DC or it would get picked up itself when the workstation restarts?
P VStorage & Virtualization  ConsultantCommented:
but XP is out of support so no guarantees of future functionality.

Yes  but XP /NT is out of support so no guarantees of future functionality.

do we have to reconnect the desktops with the new DC or it would get picked up itself when the workstation restarts?

NO , it will picked up the same
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Aussy99Author Commented:
Thanks for reply.

does the new exchange server reconnect with workstations itself or do we require to connect workstations again.
P VStorage & Virtualization  ConsultantCommented:
that conector is only to connect between exchange servers once you transfer all the mailboxes to new server then all the clients will connect to New server automatically
Alex GreenProject Systems EngineerCommented:
would the computers with win xp or windows NT work with new domain level in server 2016?

NT Will NOT talk to this at all, in any respect, support for it fell out in windows 2008, that's 2008 not 2008R2.

XP will talk to it but even then, upgrade for the win :D
Lee W, MVPTechnology and Business Process AdvisorCommented:
Given your questions so far, I would strongly recommend you contact a professional with experience and understanding to woork with you to perform this upgrade.  If you have the systems you imply you do, doing it yourself COULD result in a nightmare that, depending on how vital the role of the server is to your business, could put you out of business or cost you FAR more in lost productivity and potentially recovery time and charges getting things working again.
Philip ElderTechnical Architect - HA/Compute/StorageCommented:
Agree with @Lee as we've both been a part of the SBS MVP fold and have run many a SBS migration. ;)

The process would be:
1: Set up VM0 as the DC and configure for data
2: Set up VM1 and install Exchange 2016 - It will automagically set itself up in migration mode

The Exchange Migration Assistant is an awesome tool by Microsoft. It covers everything for the needed steps.

1: FSMO Roles would be the last thing to transfer to the new DC once ready to remove SBS (post Exchange removal and data migration).
2: Jeff Middleton's SwingIT Migration could be used to transparently migrate.

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Aussy99Author Commented:
We have successfully used Jeff swing tools in past to perform sbs migrations, but his site is not working anymore and no help either. Thanks for the useful information, that give confidence in doing the migration. The only concern bit is the win NT workstations which are connected to the network since we cant take them offline.

We noticed yesterday while checking the forest that its still in 2003 mode and upgrading it to 2008 mode might or might not affect the connections with NT computers.
Aussy99Author Commented:
on contrary we are thinking of migrating just the exchange from sbs to 2016 and keep sbs as DC, please advise thoughts.
Philip ElderTechnical Architect - HA/Compute/StorageCommented:
The catch with that is the SBS license. It must remain at the root of the domain and hold all FSMO Roles. Having Exchange removed does not impact the SBS license.

The other catch is holding back the AD Forest and Domain levels to 2008 R2.
Aussy99Author Commented:
we tried to install exchange 2010 sp3 today and its asking us to install exchange server first, we already have exchange 2010 installed and running on this server, any advise please.
Philip ElderTechnical Architect - HA/Compute/StorageCommented:
What Exchange service pack is already installed if any? Install the next one up. So, SP1 or SP2 before SP3 then the latest update rollup.
Aussy99Author Commented:
thanks for comment Philip, sp3 is installed and all good now.

would the exchange 2016 migration happen in forest and domain mode 2003?
Philip ElderTechnical Architect - HA/Compute/StorageCommented:
This says 2008 and later. So, both Forest and Domain do indeed need to be elevated.
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