Windows server upgrade

[DimitriP]

It's  October 2023.
Server 2016 is "out of support" and about to be  replaced with Server 2019 .
It's still October of 2023.
Any thoughts ?

[golden_labels]

If you still have applications, that require Windows Server 2016, you have a few more years to find replacements. Extended support continues for the next 3+ years.

[Halcyon]

My thoughts are, don't replace one obsolete OS with another.

There have been plenty of recent critical vulnerabilities impacting Windows Server 2019 and although they are being patched, mainstream support ends in 3 months. While you'll still receive (some) security updates, depending on your use-case, it may still be a risk to an organisation.

My question would be, why wouldn't you use Windows Server 2022, or perhaps even Linux?

[nightfire]

At work, we have some remains of Server 2016, which are currently replaced by Server 2019.
My experience: 2016 has still some time left in the extended support timerame, but as lots of systems were running now for some time, they have serious issues in getting new monthly patches installed.

Reason: Windows keeps track of the installed patches (THe WinSXS folder), and sometimes the background mechanisms to clean out replaced patches etc. does not work correctly.
Then you can try to clean that manually with the DISM command, and install patches manually.

On the other hand, the 2019 Servers run just fine and behave well.
The trick is, to buy 2022 licenses, because you have a downgrade right, so that they also cover previous versions, and later they allow an upgrade to the 2022 server.
As our workload is still mainly on 2019 server, and we have some datacenter licenses, we are happy with them, so the next 1 or 2 years we will continue using 2019 servers.

[Haenk]

There is always the option to testdrive the server; without license, you can run the full installation for 180days. Without any limitations (other than a little hint on the windows desktop).
MS even allows you multiple "rearm"s, to prolong the test phase.

So you could easily check out the latest version, without having to buy upfront. If it works - great - then just buy a license.

[Jackster]

Be sure to test new OS before deploying. Best to go with latest release that is not beta.
I have some very old code running on 2019 and it does not work on 2022. Completely nonsensical but it is so basic it should just work but it doesn't.

[DimitriP]

At work, we have some remains of Server 2016, which are currently replaced by Server 2019.

Ok, but as it was so eloquently put above:   

My thoughts are, don't replace one obsolete OS with another.

There have been plenty of recent critical vulnerabilities impacting Windows Server 2019 and although they are being patched, mainstream support ends in 3 months. While you'll still receive (some) security updates, depending on your use-case, it may still be a risk to an organisation.

My question would be, why wouldn't you use Windows Server 2022, or perhaps even Linux?

I've been trying to see the point of such a move other than someone selling an "upgrade" aka excuse for an invoice!

[Halcyon]

I've been trying to see the point of such a move other than someone selling an "upgrade" aka excuse for an invoice!

If an organisation it looking to upgrade, either through necessity (the current solution isn't doing its job anymore) or it's just getting a bit old in the tooth (lack of available replacement parts, old software that might be vulnerable to exploits), then why not just go the whole hog and have it last another 5-10 years?

I think if you're looking at Windows Server 2019, you're just going to be in the same position in a few years.

I understand that there might be some edge cases where old hardware/software support needs to be maintained, but those should be considered carefully on a case-by-case basis with appropriate controls in-place to mitigate (or accept) any risks.

[golden_labels]

I've been trying to see the point of such a move other than someone selling an "upgrade" aka excuse for an invoice!

Putting what Halcyon said into another perspective: the buyer is so far behind with updates schedule, that even the version following their current one is becoming outdated soon. What is the point in updating to Windows Server 2019, if one has to instantly work towards discarding it and moving to Windows Server 2022? Visually:

Code: [Select]

R
E                           ╭──WS2022─────────────┬┄ ┄ ┄ ┄ ┄ ┄ ┄ ┄ ┄╮
L                           ╵
E               ╭──WS2019─────────────┬┄ ┄ ┄ ┄ ┄ ┄ ┄ ┄ ┄╮
A               ╵
S   ╭──WS2016─────────────┬┄ ┄ ┄ ┄ ┄ ┄ ┄ ┄ ┄╮
E   ╵
┄─┼───┼───┼───┼───┼───┼───┼───┼───┼───┼───┼───┼───┼───┼───┼───┼───┼───>
 ’15 ’16 ’17 ’18 ’19 ’20 ’21 ’22 ’23 ’24 ’25 ’26 ’27 ’28 ’29 ’30 ’31
PHASE         ░░░▒▒▒▒▒▒▓▓▓██WS2016
 OUT                      ░░░▒▒▒▒▒▒▓▓▓██WS2019
                                      ░░░▒▒▒▒▒▒▓▓▓██WS2022 (estimated)
                                  ^
                     here we are ─╯
                                                                       

And that assumes some preparations for a move are already happening. Otherwise, depending on the size of the organisation and its dependency on old software, with security updates available for a few more years it may be even saner to rather aim for a move to the next (unnaounced) release. Because, if the updates were neglected, it’s possible the entire shift will end when WS 2022 itself is outdated.

[evaadms]

Windows Server 2016 was released for general availability on Oct. 12, 2016, and was developed concurrently with Windows 10. Mainstream support for Windows Server 2016 ended on Jan. 11, 2022.

[50ShadesOfDirt]

You paid for that software, and you should use it forever, or at least until something changes on your end that *forces* an upgrade. You didn't "rent" it, like a car lease period, and now you have to give it back.

"Out of support" is kind of like a "best if used by" date on food or medicine, and it is the vendor's suggested time frame for "we want you to buy the next release, for another amount of money" ... we don't really want to support you any longer with that release. If you can keep it running, and there's no pressing reason for *you* to upgrade it, then keep using it. The software is still fine, and functioning as it was intended, with the features it came with. I have come across some orgs that still have very old server versions running ... some radio sites probably still have old dos systems running.

Just pay attention to security vunerabilities, and determine if they really apply to your use of the server software. There are organizations that are required by their security policies to mitigate all vunerabilities, upgrade to the latest versions of software, etc. ... don't know what your scenario is, from OP.