SBS 2011 standard migration to windows server 2016 essentials - Advice please

SBS 2011 standard migration to windows server 2016 essentials - Advice please

I've been tasked with upgrading a SBS 2011 Standard server with Windows Server 2016 Essentials on new hardware. At present, the client has 12 users, running the server as file storage and on-premise Exchange 2010. Customer does not use SharePoint. Customer would like to migrate to Exchange Online.

This customer is new to me so I don't have the benefit of the current server’s history or any past/potential problems that have or may occur.

I would like your advice on the best (least problematic) way forward. Do I:

1) Migrate on-premise exchange to Exchange Online. Once complete, disable on-premises exchange services. Leave for a week to ensure email is okay and client happy. Then either:

a)      Create brand new domain using windows Server 2016 Essentials and join clients to new domain.
b)      Migrate SBS 2011 Std to Windows Server 2016 Essentials

If I migrate, is there a chance of bringing problems over from the old server (if any exist)?

I welcome your thoughts/comments
Who is Participating?

[Product update] Infrastructure Analysis Tool is now available with Business Accounts.Learn More

I wear a lot of hats...

"The solutions and answers provided on Experts Exchange have been extremely helpful to me over the last few years. I wear a lot of hats - Developer, Database Administrator, Help Desk, etc., so I know a lot of things but not a lot about one thing. Experts Exchange gives me answers from people who do know a lot about one thing, in a easy to use platform." -Todd S.

Cliff GaliherCommented:
Unless you have a very good reason to rebuild, I recommend migrating. Rebuilding basically means new user accounts, new profiles, a need to touch every desktop, and user interruption.

Experts Exchange Solution brought to you by

Your issues matter to us.

Facing a tech roadblock? Get the help and guidance you need from experienced professionals who care. Ask your question anytime, anywhere, with no hassle.

Start your 7-day free trial
LMG09Author Commented:
Thanks for your prompt response - Is there any possibility of bringing over issues (e.g. incorrect/corrupt setup) from the old server to the new server?
Cliff GaliherCommented:
That rather an open ended question. And the answer is "it depends." It depends on what was misconfiguration or corrupt.
LMG09Author Commented:
Thanks for your prompt response. Unfortunately, it is an open ended question because I've not been able to a assess the current server in detail yet. I've decided that migration is the way. Once again thanks for your input.
It's more than this solution.Get answers and train to solve all your tech problems - anytime, anywhere.Try it for free Edge Out The Competitionfor your dream job with proven skills and certifications.Get started today Stand Outas the employee with proven skills.Start learning today for free Move Your Career Forwardwith certification training in the latest technologies.Start your trial today
Windows Server 2016

From novice to tech pro — start learning today.