SERVER UPGRADE: 2008 R2 Standard to 2016 Standard

[G33kman]

OK so I'd like to start off by saying I'm just starting to look at my options here I would like to get a clear understanding of things before I start actually doing anything with our network...

 

Main Server Specs:

(08SRV) Dell PowerEdge T320

 

OS: Windows Server 2008 R2 Standard

CPU: Intel Xeon E5 2420 @ 1.90GHz

RAM: 16GB Triple-Channel DDR3 @ 666MHz

RAID CONTROLLER: Dell PERC H310 (RAID 1)

HDD: 2 x 1TB SCSI

 

Backup Server Specs:

(WS2012) HP ProLiant ML350 G6

 

OS: Windows Server 2012 R2 Standard

CPU: Intel Xeon L5506 @ 2.13GHz

RAM: 6GB Triple-Channel DDR3 @ 399MHz

Raid Controller: P410i Controller

HDD: 2 x 136GB SCSI - 2 x 1TB SCSI

 

Computer Specs:

Custom Computers

OS: Windows 10 Pro x64

CPU: Intel Core i5 7600 @ 3.80Ghz

RAM: 16GB Dual-Channel DDR4 @ 1196MHz

HDD: Samsung 850 EVO SSD (500GB)

 

So I'm looking at upgrading the main server to 2016 Standard from 2008 R2 Standard. I have a copy of 2016 that is not being used at the moment and would like to make use of it but I am not sure if it's going to be worth the upgrade for this hardware for one and not sure if 2016 is a good upgrade path.

 

We are a small office that use the Server for Active Directory (Domain logins), DHCP, DNS, File Shares, Printer Sharing, and IIS

Just looking to see what peoples thoughts are on the situation.

Thanks,

Ryan

[leadeater]

Are there any features of Server 2016 that you want to make use of that are not in Server 2008 R2? Is it worth your effort to go through the upgrade if there isn't anything to be gained at the end of it?

 

I would wait for a hardware replacement if the answer to the above is no, it would also be much easier and side by side migrations are at lot easier and safer than in-place/rebuild migrations.

[G33kman]

Well to be perfectly honest I would like to use some of the new features (containers and possibly the nano installation) but I don't NEED any of the new features. I am not planning to do anything for a while just trying to plan ahead. We bought this server 2 years ago and aren't planning to upgrade any time soon. I know 2008's EOL is in 2020 so I'd like to be moved to something new by that time. That's 2 1/2 years away so plenty of time for me to plan this out and figure out everything.

[Electronics Wizardy]

11 minutes ago, G33kman said:

Well to be perfectly honest I would like to use some of the new features (containers and possibly the nano installation) but I don't NEED any of the new features. I am not planning to do anything for a while just trying to plan ahead. We bought this server 2 years ago and aren't planning to upgrade any time soon. I know 2008's EOL is in 2020 so I'd like to be moved to something new by that time. That's 2 1/2 years away so plenty of time for me to plan this out and figure out everything.

Well you probably should upgrade to 2016 due to support.

 

Upgrading looks like its gonna be a lot of manual working setting things up, as there is no easy upgrade program from microsoft.

 

Id also look at running things in hypver-v vm's(you have 2 licences incuded in 2012 and 2016 standard). This could make hardware upgrades in the future easier, and its also easier to move to amouther server if you want to(you can do it without rebooting anything)

 

 

[leadeater]

3 minutes ago, Electronics Wizardy said:

Well you probably should upgrade to 2016 due to support.

 

Upgrading looks like its gonna be a lot of manual working setting things up, as there is no easy upgrade program from microsoft.

 

Id also look at running things in hypver-v vm's(you have 2 licences incuded in 2012 and 2016 standard). This could make hardware upgrades in the future easier, and its also easier to move to amouther server if you want to(you can do it without rebooting anything)

Yea I was going to say if going ahead with the upgrade move to VMs and make use of the right to run two virtual instances with a single Standard license.

 

@G33kman

You'll have to think about how you are actually going to do the upgrade. Is the backup server also a DC? You'll need a second one to be able to take down the primary for the migration work, I think it is from memory of another post you made?

 

I'd make one VM the DC, DHCP, DNS and another for File, Printing and IIS.

[G33kman]

Yeah as far as setup goes I plan to spend a weekend getting everything setup since no one will be in the office. I will be backing files up and setting everything up from scratch if I do this upgrade. So I'll have plenty of time to do things without being rushed.

[G33kman]

7 minutes ago, leadeater said:

Yea I was going to say if going ahead with the upgrade move to VMs and make use of the right to run two virtual instances with a single Standard license.

 

@G33kman

You'll have to think about how you are actually going to do the upgrade. Is the backup server also a DC? You'll need a second one to be able to take down the primary for the migration work, I think it is from memory of another post you made?

 

I'd make one VM the DC, DHCP, DNS and another for File, Printing and IIS.

Yeah you're correct the backup is a DC as well. I would really like to take advantage of two VM's for sure.

I'd just like to get away from 2008 since it's EOL is around the corner technically. I figure if I start planning things out now I should be able to get things moved over and running smoothly before that happens.

[Blake]

On 4/25/2017 at 4:08 AM, G33kman said:

Yeah you're correct the backup is a DC as well. I would really like to take advantage of two VM's for sure.

I'd just like to get away from 2008 since it's EOL is around the corner technically. I figure if I start planning things out now I should be able to get things moved over and running smoothly before that happens.

No way to convince management to get a new physical box? Just thinking the T320, is going to be out of support also/cost of support will likely be cost prohibitive at this point. 

 

Also, I'd try to stay away from an in place upgrade if possible. spin up a new system, and migrate the role individually (i.e. migrate the FSMO roles to make the 2012/2016 VM the PDC, make sure everything is replicated to new system power down 2k8 box, make sure nothing breaks, etc etc).

[samiscool51]

2016 is a B***H to handle

stay on 2012 R2, you (and your sanity) will be thanking me for the warning

also don't use 2016 as a DNS (or other server that has to stay on 24/7) as the system auto reboots everytime there is an update

there is an option to turn this off in policies

the second post explains how to disable it permanently and still update system, their is also a reddit link but i haven't checked that out:

https://www.experts-exchange.com/questions/29003500/Windows-Server-2016-Disabling-Automatic-Updates-Reboot.html 

[Blake]

1 hour ago, samiscool51 said:

2016 is a B***H to handle

stay on 2012 R2, you (and your sanity) will be thanking me for the warning

also don't use 2016 as a DNS (or other server that has to stay on 24/7) as the system auto reboots everytime there is an update

there is an option to turn this off in policies

the second post explains how to disable it permanently and still update system, their is also a reddit link but i haven't checked that out:

https://www.experts-exchange.com/questions/29003500/Windows-Server-2016-Disabling-Automatic-Updates-Reboot.html 

He's going to have an AD environment, spinning up a WSUS VM wont really be that difficult, so that issue is voided.

Really, should be using cluster aware updating anyway to prevent a production server from just rebooting and taking everything down, this would also sort out the DNS/HA issues. In all seriousness, why would you run a mission critical service that requires 24/7 up time on a single server without a way to mitigate a server reboot/single point of failure?

 

Looking at his list of services:

Active Directory, will have the 2012r2 box as a failover.

DHCP, can be configured as active/active or active/passive with the 2012r2 box.

DNS, will most likely be integrated with AD, I'd assume that 2k16 would be primary DNS and 2k12r2 as secondary, no issues here assuming only one system goes down at a time).

File Shares, setup a DFS share and then your good on this side also (assuming you have enough space on both servers).

Printer Sharing, I haven't had to look at this one for a long time, but I know you can cluster this service bac in 2k3 days so i am assuming you still can. worst case scenario people can just not print for a day or two (which is fine 99% of the time unless you work in a printing press shop....). 

IIS, Bit more complicated if your doing network load balancing etc, but there isn't any reason this couldn't be Clustered, it'll really depend on the application pools, etc.

[Erkel]

Terminal services is rather broken in 2016,  Gave up on our main production TS and switches uses back to the 2008 R2,  To many issues, will do a rebuild from scratch when I get bored.

 

I personally do not do major upgrades, Either new builds on new hardware / VM,  or pull the disks out and install onto new disks if needing to use the same server.  Reverting back is easy that way, just pull the disks out and put the old ones back in. 

[leadeater]

5 hours ago, Erkel said:

Terminal services is rather broken in 2016,  Gave up on our main production TS and switches uses back to the 2008 R2,  To many issues, will do a rebuild from scratch when I get bored.

Yea tons of issues with RDS atm, general consensus is even though it supports upgrading a 2012 R2 farm don't do it as it causes database corruption for the connection brokers. So only a brand new clean 2016 farm is a viable option right now, if that also isn't full of critical issues as well.

[leadeater]

5 hours ago, Erkel said:

I personally do not do major upgrades, Either new builds on new hardware / VM,  or pull the disks out and install onto new disks if needing to use the same server.  Reverting back is easy that way, just pull the disks out and put the old ones back in. 

I do the same, also before the VM days I used to remove a disk in the OS mirror before doing any significant maintenance or changes so if it all goes wrong I could just put in the unmodified disk and be back up before the changes, then insert the bad disk and wait for the array to heal and try again. Physical server snapshot .

[G33kman]

Well that's a lot of information! Thanks for the input guys. It looks like I will be steering clear of WS2016 for now. I would love to upgrade to a new Server but being a small business (6 employees in the office) we're not able to put a lot of money towards upgrades too often. I just built new computers a few months back so buying a new server at the moment probably isn't in the budget. Lol

I am sure I can start planning things out and by the time we'll need to upgrade I might be able to replace the old Server with the current one and install a new server but that'll be down the line for sure.

Thanks for the help I'm definitely learning a lot!

[leadeater]

50 minutes ago, G33kman said:

Well that's a lot of information! Thanks for the input guys. It looks like I will be steering clear of WS2016 for now. I would love to upgrade to a new Server but being a small business (6 employees in the office) we're not able to put a lot of money towards upgrades too often. I just built new computers a few months back so buying a new server at the moment probably isn't in the budget. Lol

I am sure I can start planning things out and by the time we'll need to upgrade I might be able to replace the old Server with the current one and install a new server but that'll be down the line for sure.

Thanks for the help I'm definitely learning a lot!

Well Server 2016 still fine to use, RDS is only one role and not one you're planning to use. I've been using it since technical preview 3 so a very long time. I wouldn't do a new install not using Server 2016 personally, servers hang around for a long time so it's good to use the newest when possible. AD/DHCP/DNS/IIS/File and Print are all stable so there isn't any reason not to use it.

 

For the above point about patching and rebooting servers that's always been a thing, it's not new to Server 2016. You need to use Group Policies to tell your servers how to handle Windows Updates as the defaults are not production appropriate.

[G33kman]

Well that's a relief. I will definitely have a look at that. Maybe I'll just use the copy of WS2016 that I have on my backup server in a VM so I can get familiar with the OS.

[NZLaurence]

Another thing to consider is that a move to 2016 requires 2016 CAL's for the users. Depending on the copy you have it might be better to up both machines to 2012 R2 using downgrade rights on your 2016 license (if it supports it). There is quite a few compelling reasons to ditch the 2008 R2 machine it you already have a full win10 environment. However a lot would depend on what type of workload you are running, being basic file and print or any sort of network applications/file database workloads.

 

Often the best upgrade path can be dedicated by the licenses you are running and not the hardware you have in a small business environment.

[G33kman]

Yeah after looking at the core licensing and CAL's I think I'll hold off on the upgrade to 2016 for now. I think 2012 R2 is what we'll upgrade to when we need to do the upgrade.

Thanks for you information. After reading up on how CAL's work now I'm glad I didn't start planning out the upgrade yet! 

[NZLaurence]

Yip. Pretty much the only time you don't need CAL's for a new version of windows server is when its run in Azure. Otherwise you need a CAL of equal or greater version for every user that authenticates against the server. Meaning if you have a single 2016 DC in your domain you need to have 2016 CALs for all users in the domain, even if all the main workloads are on the 2012 R2 machines.

 

Basically, If you have the license for the server you will get better mileage by upgrading your other server to 2012 R2 and building out some form of HA between the two at a service level.

 

Windows Server 2016 has some cool features but in an SMB environment none of them are likely to be must haves.

[G33kman]

Yeah that's kind of what I'm gathering. Lol I'm going to be looking into my options for an upgrade since I would like to move that server over to the failover spot. I have a retail copy of 2012 R2 so I should be able to transfer it to that Server and get an upgrade to run as the main DC. That's my thought process as of right now at least.