Windows Server 2008 upgrade path help

[shaiknbaik]

Hello I am a new Sys Admin and was hoping to get some help regarding some servers. I need help with the logistics of getting some server upgraded from windows server 2008 up to 2016 (cant go to 2019 for other reasons). From what I have seen you have to upgrade to 2012 and then 2016, How do you go about this in terms of licensing? Do I need to buy a 2012 key and then a 2016 key? Is there a way to upgrade to 2012 without activating and then activate once I get to 2016 or do I need an active key at each step? Lastly I saw mention of buying a 2016 key and downgrading to 2012 would this downgraded key be able to active on 2012 and then up to 2016 or would I have to buy 2 2016 keys and use one for the downgrade to 2012 and one for the upgrade to 2016?

Thank You!

 

Note: I am unsure if these machines are 2008 r2 or not and I cannot confirm this until tomorrow, In addition one machine is windows Storage server 2008 and I am unsure if this will cause an issue.

[jaslion]

You can upgrade to them unlicensed no problem just gets a 30 day trial.

[Vishera]

18 minutes ago, shaiknbaik said:

Note: I am unsure if these machines are 2008 r2 or not

If it's not 2008 R2 then you will have to upgrade to 2008 R2 and then 2016.

[shaiknbaik]

13 minutes ago, Vishera said:

If it's not 2008 R2 then you will have to upgrade to 2008 R2 and then 2016.

Yeah 2008 - 2008 R2- 2012 - 2016 for the path if I am not mistaken

[shaiknbaik]

26 minutes ago, jaslion said:

You can upgrade to them unlicensed no problem just gets a 30 day trial.

Gotcha so lets say I upgrade from Windows Server 2008(activated) to 2008 R2(not activated) to 2012(not activated), and then to 2016 and try to active 2016 should I have any issues with only a single 2016 key? Thank You

[jaslion]

1 minute ago, shaiknbaik said:

Gotcha so lets say I upgrade from Windows Server 2008(activated) to 2008 R2(not activated) to 2012(not activated), and then to 2016 and try to active 2016 should I have any issues with only a single 2016 key? Thank You

Should work just fine. R2 upgrade was meant to be seamless as possible.

[Vishera]

49 minutes ago, jaslion said:

Should work just fine. R2 upgrade was meant to be seamless as possible.

Yep,I did the upgrade from 2008 to R2 back in the day and it was great,

and the backwards compatibility with 2008 programs was excellent.

[shaiknbaik]

57 minutes ago, Vishera said:

Yep,I did the upgrade from 2008 to R2 back in the day and it was great,

and the backwards compatibility with 2008 programs was excellent.

Awesome thank you very much, I dont forsee app compatability being too much of an issue the server only do pretty basic things (Exchange, Active Directory, and File Server). Do you happen to know if I can use the evaluation ISO's on the Microsoft site to upgrade? https://www.microsoft.com/en-us/evalcenter/evaluate-hyper-v-server-2012-r2 Not sure if you can use an Evaluation ISO to upgrade a standard retail software on a server?

[Vishera]

41 minutes ago, shaiknbaik said:

Awesome thank you very much, I dont forsee app compatability being too much of an issue the server only do pretty basic things (Exchange, Active Directory, and File Server). Do you happen to know if I can use the evaluation ISO's on the Microsoft site to upgrade? https://www.microsoft.com/en-us/evalcenter/evaluate-hyper-v-server-2012-r2 Not sure if you can use an Evaluation ISO to upgrade a standard retail software on a server?

I have no idea,i have never used an evaluation ISO for an upgrade.

[shaiknbaik]

28 minutes ago, Vishera said:

I have no idea,i have never used an evaluation ISO for an upgrade.

Gotcha alright thank you very much for the help!