Active Directory and Exchange upgrade from 2003 to latest

I am now responsible for a very old 2003 environment with 2003 AD, 2003 Exchange and several 2003 servers.  I would like to do long term upgrade to AD2016 and on premises Exchange 2016.  Can the AD upgrade go directly to AD2016 (via additional new servers) and then a new Exchange 2016 server while still support existing 2003/2008/2012 servers with Win 7 end user devices ?  Would like to preserve existing domains (two) and upgrade the AD to 2016 first and then do an inplace/onsite migration from Exchange 2003 to Exchange 2016.

Lastly, there are still some Windows XP machines - I assume they must go ??
jtd1Asked:
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Todd NelsonConnect With a Mentor Systems EngineerCommented:
Take a look at the Exchange Supportability Matrix.  It will provide you a frame of reference for what is currently supported.

NOTE: Exchange 2003, 2007 and 2010 are not supported with a Windows 2016 DC.

At a high level, the following would be my ordered plan of attack...

  1. Transition from Exchange 2003 to 2010
  2. Decommission Exchange 2003
  3. Upgrade AD to Windows 2008 R2
  4. Demote all Windows 2003 DCs
  5. Raise FFL/DFL to Windows 2008 R2
  6. Upgrade all Office 2007 and older clients to Office 2010 or newer (Outlook 2007 will not connect to a mailbox on Exchange 2016)
  7. Transition from Exchange 2010 to 2016
  8. Decommission Exchange 2010
  9. Upgrade AD to Windows 2016
  10. Demote all Windows 2008 R2 DCs
  11. Raise FFL/DFL to Windows 2016 (as needed)

There will for sure be several client and application dependency upgrades that need to take place before introducing Exchange 2016 and Windows 2016.  So, do your homework.
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Mark BillExchange, AD, SQL, VMware, HPE, 3PAR, FUD, Anti MS Tekhnet, Pro EE, #1Commented:
You have the right idea in the order to do things, AD first and then Exchange. Outlook versions are key with Exchange what are they on the site?
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Mark BillExchange, AD, SQL, VMware, HPE, 3PAR, FUD, Anti MS Tekhnet, Pro EE, #1Commented:
From my research there seems to be no upgrade path, this will cover you for a 2003 to 2012 upgrade though

https://blogs.technet.microsoft.com/canitpro/2014/04/01/step-by-step-active-directory-migration-from-windows-server-2003-to-windows-server-2012-r2/
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Mark BillExchange, AD, SQL, VMware, HPE, 3PAR, FUD, Anti MS Tekhnet, Pro EE, #1Commented:
XP and 7 machines should be gone these days in my opinion. Both insecure and I was a big 7 fan.
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jtd1Author Commented:
Don't have an option on end user Win 7 devices - they are what they are.  We will be able to get rid of XP however and probably replace with Win 10.   $$$$ is a HUGE issue at this customer so this upgrade will be the last for another 10 years so need to start upgrade with absolute latest if possible.  From the response I have seen no way to go from AD2003 to AD2016 directly ? Current Outlook versions are 2010 so  as long as updated should work from what I can tell.

If I cant get an upgrade path that is cost efficient (from a man hours perspective, they may go to non-integrated Exchange Online (Office 365) solution.
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Mark BillExchange, AD, SQL, VMware, HPE, 3PAR, FUD, Anti MS Tekhnet, Pro EE, #1Commented:
As of some point in 2016 there was no path from 2003 to 2016 that I can find, this may have changed, it is hard for me to be 100% certain, I do not like to give bad information on here.

Is the active directory / company data in a place where you could consider this? obviously this has its issues potentially and this solution is environment specific and never something I really recommend as a first idea.

Creating a brand new AD on a seperate VLAN/Network, Build your Exchange set it all up, during a scheduled window migrate all the neccesarry AD data and any other needed data + PSTS to Exchange. Joining up PCs etc. Just an idea.

Will check up on the upgrade path again now.
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Mark BillExchange, AD, SQL, VMware, HPE, 3PAR, FUD, Anti MS Tekhnet, Pro EE, #1Commented:
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DrDave242Connect With a Mentor Commented:
I'd only add one thing right at the top of Tood's list: Back up everything before you begin. If the whole migration spins off the track, rolls into a ditch, and bursts into flame, you'll want to be able to tell your boss, "I can at least get things running again in an hour or two," rather than, "We have to rebuild everything from scratch."
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jtd1Author Commented:
An hour or two - that funny - this hardware is 10-15 years old.  Were afraid to even reboot or power them off.  Thanks everyone - will examine your thoughts in detail shortly
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Mark BillExchange, AD, SQL, VMware, HPE, 3PAR, FUD, Anti MS Tekhnet, Pro EE, #1Commented:
Nice break down from Todd on the exact steps, does not look to pretty if you are stuck for time. Good luck with this one guys.
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DrDave242Commented:
An hour or two - that funny - this hardware is 10-15 years old.

Point taken! OK, maybe more than an hour or two, depending on just how much needs to be restored. Still, back it up first.
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jtd1Author Commented:
Thanks everyone for your input. I feel like I have a solution to work with. One last question.  If I was to decide to start with a brand new environment, can the old 2003 AD environment be a trusted partner to a new 2012 or 2016 AD ?
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Mark BillExchange, AD, SQL, VMware, HPE, 3PAR, FUD, Anti MS Tekhnet, Pro EE, #1Commented:
I think with your time constraints it is probably better to go with the clean setup if an option. Manual AD migration as AD DB's and data are very very small in general.
Just keep all of the old kit no need for a trust IMO, problem with this trust again would be no support from Microsoft. Not a situation I fancy landing myself in on a client site.
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jtd1Author Commented:
Mark

Not sure I follow your approach.  Are you saying I can manually build the AD of a new 2016 environment with a "seed" from the old ?
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Mark BillExchange, AD, SQL, VMware, HPE, 3PAR, FUD, Anti MS Tekhnet, Pro EE, #1Commented:
I should explain better apologies.
I thought you said you are going to go with a clean new fresh AD domain and made my comment to align with that.

If you are under time constraints and cost constraints the literal step by step upgrade paths are not good options right?
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jtd1Author Commented:
you are completely correct.

If there was a way to create a complete new environment that has some sort of passthrough abilities from desktops on the old domain(s) then I would be golden. Unfortunately there is no way that I know of for a PC to be a member of two different domains
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Todd NelsonSystems EngineerCommented:
Sufficient information provided for solution.
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