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Jon_AK

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Reply with quote  #1 
Hi, been a while since last visiting.  Have been checking around to find the requirements for upgrading 2008R2 to 2016.  At the moment I do not have the luxury of having another dedicated box to migrate into but am hoping management will spring for one.  At any rate, our one and only server is a PDC on active directory and our organization has a subscription to office365 / exchange online / sql online.  Would anyone care to point me to a document for performing the upgrade or migration? 
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wobble_wobble

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Reply with quote  #2 
Best link I've seen. Its 2012 but the process is the same for 2016
https://blogs.technet.microsoft.com/canitpro/2013/05/05/step-by-step-adding-a-windows-server-2012-domain-controller-to-an-existing-windows-server-2003-network/

Few questions.
Do you intend to do an inplace upgrade?
Do you have DirSync or Azure AD for your O365 tenancy?

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Jon_AK

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Reply with quote  #3 
From the reading I have done thus far, I would prefer to do a migration to a separate machine but may have to settle for an in-place upgrade.

We do have DirlSync which I believe was replaced with Azure sync.  That is the part of the upgrade / migration that most concerns me.  I'm reasonably comfortable with the active directory migration as the steps seem pretty straight forward but am concerned with the O365 / Azure sync since my employer hired a company to perform a migration from what was our IBM Domino/Notes system to Office 365.  Needless to say, the company that was hired for that migration can smell blood a mile away (shark) and will cost literally thousands to bring them in again.  It may be that will have to happen if I don't feel 100% confident I can perform it. 
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wobble_wobble

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Reply with quote  #4 
If an AD upgrade dont phase you then Azure AD Sync is a doddle.
Remember AADC is just replicating some attributes from AD on-premise to Azure AD.
You need three things for AADC migration.
Username and password for on-prem account used to sync.
Username and password for O365 account used to sync.
The OU's you are syncing to O365.

Next, do you have ADFS?

Edit
Apologies its AADC Azure AD Connect not AADS.
Changed AADC for AADS

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Jon_AK

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Reply with quote  #5 
That certainly sounds simple enough, at least it sounds as straightforward as performing a domain rename... which I would not like to experience again even though it went through smoothly, just all the "other" client software settings afterward.  For the AADS, is this a downloadable item that I would run and provide the necessary information for?

As for the ADFS, no... our organization is rather small - 20 users with no satellite locations or need for "out of the local domain" access.
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wobble_wobble

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Reply with quote  #6 
Apologies its AADC Azure AD Connect not AADS.

AADC is a better download than DirSync. Just Google AADC Download.
Works better.
But spend a bit of time reading the docs, a good education.
If you want the Microsoft MVA has quite a few videos on the process. If the Shark still supports the install ask thrm for the usernames and passwords for the accounts. They could also furnish you with andemo 90 day tenancy to sync against....but may charge for it (its free for partners and we get 6 active accounts at a time)
AADC can also be installed in staged mode, to check if all is OK or be used in larger orgs for DR/BCP.

So document your current config.
If you dont have the passwords for the account you can reset them.
Then check the OU's sync'd.

Experience tells me to install this on another server if your paraniod. Then shut down networking to dirsync and sync AADC.

You can then either expire the old dirsync server or remove dirsync, install AADC in staged mode, shutdown the temp one and start new one.


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Jon_AK

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Reply with quote  #7 
Appreciate the input.  At least I have time to plan for this one, I wasn't afforded the time to plan when the domain rename had to happen.  I do believe I'm going to push for a new box so now the wish list begins to be generated... hmm, dual xeon cpu's and 64g of ram?  sounds like a gamers best dream.  At any rate, I have all of our discussion and will definitely use what you have provided. 
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Wes

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Reply with quote  #8 
Sounds like the perfect time to virtualize.  Can you afford a little downtime?  If so, get your services shut down and disk2vhd your current server to a vhdx on proper storage.

If you're able and paranoid, use any hyper-v capable box - desktop, workstation, whatever and try to boot up a vm with the vhdx to make sure it's bootable and happy (don't connect it to a real network).

Assuming you're all good, rebuild the server with 2016 and add in the hyper-v role then import and fire up your VM (ideally keeping a separate copy of the vhdx if you have enough storage somewhere).  In-place upgrade to 2012r2, then in-place upgrade that to 2016.
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Jon_AK

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Reply with quote  #9 
I don't get much time when the network isn't being used full time.  I like the idea and have read some about it in the past but I don't believe there will be enough time to fully put everything into play since I'm the only one that this job would fall on (1 person tech support / software bug remedier / please restore the file I accidentally/purposely deleted a week ago in a 20 user network) to complete and my day to day job already keeps me working 10 hours (5am - 3pm).  Let me rehearse this to make sure I understand....  Once the vhdx is placed onto a separate machine and it boots and runs fine (no network though), I would install 2016 onto a new drive (planned on getting a new machine anyway) and once the hyper-v role is added and running, import and run the vhxd system in its own VM.  Since I would essentially be adding a second server by importing the older installation, what will be the MS licensing requirements?  I haven't read up on that yet.  I had also planned on upgrading to a machine with a Xeon processor.  What kind of difugleties can I expect to encounter by upgrading the hardware at the same time?
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Wes

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Reply with quote  #10 
Would they consider budgeting for a consultant to help you with this project?
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dennis-360ict

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Reply with quote  #11 
Well, you got until jan 2020 until ws08r2 goes EOL..
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