Windows Server 2008 R2 Upgrade

[J4K]

On 11th January 2020 Microsoft are ending all support for Windows Server 2008 R2.

 

I started working for my new employer around 5 months ago and we operate across a multi-site environment using a single Server 2008 R2 domain controller for all sites (5 offices in 5 different towns) and no virtualisation. The server is a relatively old Tandberg branded setup with only 4Gb RAM and a single 2Ghz Xeon E5504. But I know that Tandberg defunct around 2010 so the server is at least 10 years old and the spec sheet on it isn't great given the size of the organisation and level of dependency on IT.

 

The organisation I work for is a national charity but as we are an independent branch, we don't get direct funding from anyone unless it's for a designated project - and even then the funding isn't massive. Which means I hardly have an IT budget to work with. My concern is that with Server 2008 R2 losing all support from Microsoft, we are going to NEED to move onto a more up to date version of Server. I know that it's possible to 'upgrade' the current server onto Server 2012 R2 but in my personal opinion, I would prefer to move across to something more future proofed such as Windows Server 2016 or 2019. But this would mean doing a totally clean install of the new OS and then migrating the servers data from backup as I know its just not viable to upgrade to these from such an old version of Windows Server.

 

My major concern comes from the fact that I believe that in order to safely move up to a more up to date version of Windows Server that we will need to purchase a brand new server? I'm the head of IT within the organisation by default as I'm the only IT employee so I'm trying to gauge what is going to be the solution moving forward. Cost is a significant factor since the organisation actually doesn't have an IT budget - even though we have over 120 PC's, laptops and other mobile devices (40 paid staff and over 90 volunteers) across the 5 sites. So this increases to the pressure on me to find a solution which will both work and be a realistic cost for the organisation. To add to the frustration, any work conducted will have to be done during business working hours since our building is leased and has a compulsory lockup between 6pm and 6am so no personnel are allowed in the building between those hours. Any ideas? Am I just overthinking the whole situation? It's a difficult one really. I just fancied getting some other technical opinions on the situation before I go into a gradual decent of madness and see whether anyone has any thoughts or alternative solutions that I haven't considered (be sensible) xD

[LukeRowberry]

If it was me I'd get yourself a new server and run them side by side until you're happy to move roles and decom the original one.

I'd also look to make it a virtual server to give you more options in the future and easier backups etc.

[FN-GM]

Do you want to PM me the information of your charity please? I may be able to provide a used server that can run Server 2019. I would have to check though.

[Chris_]

Based on the information from Microsoft here https://docs.microsoft.com/en-us/windows-server/get-started-19/install-upgrade-migrate-19 I've upgraded a couple of 2008 R2 servers to 2019 by upgrading to 2012, then 2016, finally 2019. However, I came across some more Microsoft documentation saying that you can go from 2008 R2 straight to 2012 R2, which would mean one less step as you can go from 2012 R2 to 2019.

 

Fortunately I'm dealing with VMs so I can take snapshots should something go wrong but I haven't needed to revert.

[yac2016]

If you are a charity is it not time to look at Gsuite or O365, both products are free for education and charity sectors.

[XiJ]

In terms of upgrading it’s definitely worth running a new server alongside the current whole you move roles across and migrate data.

And wouldn’t even think about anything non-virtual.

 

It could be you look at refurb’d servers. You could run 2016/1019 hyper-v core to help cut down on OS resources. You’ll need storage and ram of course.

 

O365/google is a very good shout though. You have 5 remote sites so ‘cloud computing’ makes a lot of sense.

[SteveB_NI]

In terms of upgrading it’s definitely worth running a new server alongside the current whole you move roles across and migrate data.

And wouldn’t even think about anything non-virtual.

.

 

Sorry to hijack this thread but I'm in a similar situation. Current set up is 2 x Servers running 2008R2. I have a brand new server waiting to be configured.... I'm debating is it better starting completely afresh (with Win Server 2019) or like you are saying install Server 2019 on the new server, configure several virtual servers and then migrate roles across? Is there many issues moving a role from Server 2008R2 up to something newer?

[J4K]

We have Office 365 already! Cloud computing isn't an option for our charity due to the nature of the information that we sometimes have to handle, we're obligated by law to ensure total data security and confidentiality and that's something which can't be truly guaranteed using our Office 365 subscription to start storing things in One Drive etc.

 

At the moment it looks like I'm going to have to get a new server and run the thing alongside the current system and just migrate stuff that way. I would love to Virtualise the new solution, but I also have to consider the type of end-users which currently use our systems. Our users are primarily Dinosaurs when it comes to computers and even migrating across to using Google Chrome from IE and Skype to Microsoft Teams has been an absolute nightmare in terms of training and getting people to understand how and why they need to use things. I've wanted to Hyper-V or VMware the new system but I just feel this would be more hassle on me than its worth - given I'm one person stretched over 50sq miles. Plus, some of our sites are only running from a max 20mbps LAN-to-LAN ADSL connection (which can be temperamental at the best of times) and can't be improved because of the local infrastructure, so working from VM's could quite easily become a massive headache.

 

SteveB_NI, I've also thought the same thing about migration from 2008 R2 to 2019. I'm guessing there shouldn't be any issues as long as all network firmware etc is up to date but it's something I'm not sure about either as I've never actually managed moving anything between servers running OS which are so far apart in age. Unless there are core differences between 2008 R2 and 2019 I don't see why migration would be difficult but again, it's something that would be good to know.

[LukeRowberry]

I'd have thought going down the hyper-v or vmware route would create less pressure on you. The end users wouldn't notice any difference but it will give you massive advantages with backup and DR.

[yac2016]

We have Office 365 already! Cloud computing isn't an option for our charity due to the nature of the information that we sometimes have to handle, we're obligated by law to ensure total data security and confidentiality and that's something which can't be truly guaranteed using our Office 365 subscription to start storing things in One Drive etc.

 

At the moment it looks like I'm going to have to get a new server and run the thing alongside the current system and just migrate stuff that way. I would love to Virtualise the new solution, but I also have to consider the type of end-users which currently use our systems. Our users are primarily Dinosaurs when it comes to computers and even migrating across to using Google Chrome from IE and Skype to Microsoft Teams has been an absolute nightmare in terms of training and getting people to understand how and why they need to use things. I've wanted to Hyper-V or VMware the new system but I just feel this would be more hassle on me than its worth - given I'm one person stretched over 50sq miles. Plus, some of our sites are only running from a max 20mbps LAN-to-LAN ADSL connection (which can be temperamental at the best of times) and can't be improved because of the local infrastructure, so working from VM's could quite easily become a massive headache.

 

SteveB_NI, I've also thought the same thing about migration from 2008 R2 to 2019. I'm guessing there shouldn't be any issues as long as all network firmware etc is up to date but it's something I'm not sure about either as I've never actually managed moving anything between servers running OS which are so far apart in age. Unless there are core differences between 2008 R2 and 2019 I don't see why migration would be difficult but again, it's something that would be good to know.

I would still virtualise the new hardware, this does not affect any users, they won't even know you have virtualised anything as it will be on the server side. It will give you many options including more VM's, backing up etc.

 

I am based in Staffordshire so happy to give you some advice if you need any.

[2097]

Having recently upgraded the following

 

2008 R2 DC / Print Server / KMS

2008 R2 DC / DHCP

 

Transfer DHCP to its own 2019 server

Transfer the Print Server and KMS to a single 2019 server

 

transferred all roles from both servers to the exisiting 2008 GC server

Decommissioned one DC

Setup a new 2019 DC ( using decommissioned name) , Joined and transfer all roles to new DC

Decommission last 2008 DC

Then setup another 2019 DC and transfer 1/2 the roles over.

 

All this is fine assuming you have enough hardware resources

 

In my opinion get a new server and run ESXI on it. If all the 2008 r2 server is doing is Domain controller dutys you should be able to do 99% of this while live !

Edited April 1, 2019 by 2097

[supportman]

Out of interest what is best practice for virtualizing a domain controller on a domain now? Should it be on an off domain Hyper-V host or on domain?

[2097]

Out of interest what is best practice for virtualizing a domain controller on a domain now? Should it be on an off domain Hyper-V host or on domain?

 

Sadly i have never used Hyper-V, Only vmware . Hoping some one will have an answer for you. Sounds to me it should be on a "Off Domain" host . Is there a reason why a Hyper-V host would be on a domain ?

[ThatBoringBloke]

Out of interest what is best practice for virtualizing a domain controller on a domain now? Should it be on an off domain Hyper-V host or on domain?

 

If your host dies and your DC is a VM on that host how would you log on?

[TwistedHelixis]

Apparently for Hyper-V it should not make a difference if it is on the domain or not as the hyper-v should cache the login details, but I have always had my hosts off the domain.