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Hello Everyone , i hope you are safe from Covid 

I currently have exchange 2010 with domain 2008R2 , i am planning to update to 2019 or 2022 (both domain and exchange)

I understood i cannot migrate from 2010 to 2019 directly and have to pass to 2016 before this 

I have several issues with that :

  1. can the exchange 2016 migration be done on a trial license ?
  2. during all of this , can the domain be upgraded to 2019 ? if yes , can it coexist with a 2008r2 domain ?
  3. how to upgrade ? i have around 100 inbox , some are heavy but most are less than 10 GB in size .. what do you advise ?

thank you all for your help 


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31 Replies

· · ·
EminentX
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For your first question as far as I know, yep, you can do that with trial version too.

1
· · ·
Rod-IT
Pure Capsaicin
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Rod-IT
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I agree, if you've licensed 2019 Exchange, you have the rights to put in a 2016 for the migration.

Do your domain side first, don't' try to both at once. Take your time and make notes. It makes it easier to undo something if it goes wrong and you know what you did.

2
· · ·
Tarek - IT manager
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how exactly ? how can i use the 2016 then 2019 ( license wise )

also can 2008r2 and 2019 domain coexist ? like can i just add another DC with higher year ?

i checked for the domain coexisting , it is possible and migration is the same as regular DC to DC ( fsmo and such ) so i add the 2019 DC before attacking exchange
0
· · ·
TheBusKing
Jalapeno
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TheBusKing

Good morning, Tarek.

Based on the Microsoft compatibility matrix, https://docs.microsoft.com/en-us/exchange/plan-and-deploy/supportability-matrix?view=exchserver-2019, you will need to have a Windows 2012 R2 Active Directory server and an AD Forest functional level of at least Windows Server 2012 R2.

You will have to transfer the roles to another Domain Controller running Windows 2012 R2 or higher and then demote the 2008 R2 DC.

I recently ran into this issue when upgrading to the latest 2016 CU. I could not do so until I removed my 2008 R2 DC and raised my AD to 2012 R2.

Good luck to you and we are here to help!

1
· · ·
Kwinza
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You wont have 2 domains. You'll have your 2008 functional level and then you'll upgrade that to 2019.

These are the steps I'd take;

1. Build your the server that you'll be using for exchange (2012r2 for now).

2. Install Exchange 2016

3. Migrate to your current Exchange up to 2016 (take a back up of the server at this point)

4. Repeat the process for Exchange 2019 and Server 2019 (backup time again)

5. Build your 2019 DC - DO NOT UPGRADE FORREST LEVEL!!!

6. Sync data between your two DC's (guess what, time for a backup)

7. Go back onto your new DC and upgrade the forrest level.

8. Decommission the 2 old servers.

1
· · ·
TheBusKing
Jalapeno
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TheBusKing

I was replying when you posted your last message. Let me know if you need more information, but you will have to add the new 2019 DC, transfer FSMO roles on your 2008 R2 DC to the new DC, demote the 2008 R2 DC and then raise the AD environment and functional level.

1
· · ·
TheBusKing
Jalapeno
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TheBusKing

Thanks, Quinza.

I forgot you’re upgrading from 2010. So, as Quinza stated you will have to upgrade to 2016 first and then build your new 2019 DC.

1
· · ·
Tarek - IT manager
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so i will be using a trial version of exchange 2016 ? is this possible ?

would a pst export/import work better for my case ?

0
· · ·
Kwinza
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Yeah just use the trial version.

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· · ·
Lucid Flyer
Habanero
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Lucid Flyer
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Technically it would work with a trial license.
If you would use PST import/export you would lose some important relationships between the mail items across users.
Use this website to build your custom migration plan from Exchange 2010 to 2016.
The same can be used for 2016 to 2019.
Make sure to follow the previously provided link for the compatibility matrix between domain and forest levels.
Each Exchange has its' own requirements for the supported levels of configuration. Make sure to review it:
* Exchange 2016
* Exchange 2019


2
· · ·
adrian_ych
Mace
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Are you asking 2 questions here or just one ??

- Upgrading DCs from svr 2008R2 to svr 2019

- Upgrading Exchange 2010 to Exchange 2019

Both have their own routes to upgrading while both can be done concurrently, I would highly recommend performing the DCs upgrade then the Exchange upgrade after the DC upgrades have completed successfully.

0
· · ·
Tarek - IT manager
Poblano
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both are related somehow , exchange and DC are very intertwined but i am looking to upgrade both ..i think i will follow Kwinza​ 's route .. 

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· · ·
adrian_ych
Mace
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Tarek - IT manager wrote:

both are related somehow , exchange and DC are very intertwined but i am looking to upgrade both ..i think i will follow Kwinza​ 's route .. 

DCs do not rely on Exchange. They should be upgraded first.

Exchange relies on certain Domain Schema from DCs. 

Then how proficient are you in DCs (no punt intended) ?  Kwinza​ only mentions upgrading the Domain Function Level or DFL (anyway only 3 OS levels so Server 2019 will not even have Server 2008 DFLs).

0
· · ·
adrian_ych
Mace
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You need to upgrade the DCs and Exchange 2x as there is a great lapse and Exchange 2016 will not work with server 2008R2 while Exchange 2010 will not work with DC2019.

1. Upgrade DC2008R2 to DC2012R2 first (before Exchange 2010).

- Install 2x DC2012R2, transfer FMSO roles to one of the DC2012R2. Wait 24 hours to 72 hours, check event logs for errors.
- Decomm 1x DC2008R2, Wait 24 hours to 72 hours, check event logs for errors.
- Power off last DC2008R2, Wait 24 hours to 72 hours, check event logs for errors.
- Decomm last DC2008R2, Wait 24 hours to 72 hours, check event logs for errors.
- Migrate to DFSR on DC2012R2 https://docs.microsoft.com/en-us/windows-server/storage/dfs-replication/migrate-sysvol-to-dfsr

2. Install Exchange 2016 on Server 2012R2 & migrate to Exchange 2016

3. Upgrade DC2012R2 to DC2012R2 first (before Exchange 2010).

- Install 2x DC2019, transfer FMSO roles to one of the DC2019. Wait 24 hours to 72 hours, check event logs for errors.
- Decomm 2x DC2012R2, Wait 24 hours to 72 hours, check event logs for errors
- Set DFL to Server 2019

4. Install Exchange 2019 on Server 2019 & migrate to Exchange 2019. This can be done at a much later time...incase you decide to move to Exchange Online (aka. MS365 without the MS Office)

1
· · ·
Slyldawg
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If no one else has noted this, then I will. Microsoft does not recommend having Exchange running on a domain controller. 

0
· · ·
MagicMike
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1st Post

Do yourself a favor and migrate to exchange online. You will need to migrate to Exchange 2016 and then to EX online. 

0
· · ·
Joz_
Datil
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Joz_
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Totally agree with what they have replied above.

In addition, here's a similar thread for your reference and hope it is helpful to you: Migrating Exchange 2010 to Exchange 2019 guide

1
· · ·
Tarek - IT manager
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there is some mix up here with the years ? what do you mean by 2x and 1x ? i see you decommissioned the 2008r2 twice or am i missing something ?

also would this work with dc2016 ?

0
· · ·
Tarek - IT manager
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it is a different server , good point

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· · ·
Tarek - IT manager
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unfortunately i am in Congo , internet is not very stable .. and we only use the exchange for internal mailing 

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· · ·
Tarek - IT manager
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found this for the domain issue - so i am forced to raise the DFL to 2012R2 minimum before adding the exchange 2019

this is starting to getting clearer , you are all very knowledgeable - thank you


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· · ·
Tarek - IT manager
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what about in place upgrade of exchange from 2010 to 2016 ?? is it doable ?! 

0
· · ·
Priyal (Stellar Info Tech)
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1 - can the Exchange 2016 migration be done on a trial license ?

Ans - You can run Exchange in standard mode for 180 days without a license if you want to use the 2016 server as an intermediate step simply.

2 - during all of this , can the domain be upgraded to 2019 ? if yes , can it coexist with a 2008r2 domain ?Ans - The minimum requirement to add a Windows Server 2019 Domain Controller is a Windows Server 2008 forest functional level. The domain also has to use DFS-R as the engine to replicate SYSVOL. According to the description, please check whether your domain functional level is 2008 in ADUC (Active Directory Users and Computers) and whether the forest function level is 2003 in ADDT (Active Directory Domains and Trusts).

3 - how to upgrade ? i have around 100 inbox , some are heavy but most are less than 10 GB in size .. what do you advise? Ans - And for large mailbox migration, you can check How to Migrate Mailboxes over 100GB to O365?

I hope this will help.

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