I think it can still continue to evolve and innovate, especially on the Security side of things where we now have TLS1.3 enabled by default, SMB improvements, AD hardening, SSO. Additionally, I think we shall all see a tighter integration with Azure Entra for Hybrid deployments. 

One of the most interesting is going to be Hyper-V and see where Microsoft heads towards that, especially with the news coming out of Broadcom and their long term plans. 

There is still a need to on-prem server deployments as we are getting to a point where some SMBs would rather run services on-prem when it comes to cost savings. 

Agree with Dipen...Win will continue being relevant and evolve, and not just for SMBs.

As Dipen shares...I wonder if MS will get off their “duff” and start really pouring into on-prem HV to compete with VMW….

I think they will continue to evolve and grow Windows Server for a little while longer.  As noted, you have to wonder if they will go in on Hyper-V to compete with Broadcom now.  It would also be nice to see maybe some containerization services added to Windows for that part of the market.

IMHO yes.  Something like 85% of Azure customers are Hybrid.  We are one of those.  On-Prem is shrinking but it will be a long time before it is gone if it ever is.

My company runs VMware for now.  However, our RBO licenses expire next month, and we got an insane quote from our VAR (RBO is gone, so standard license at new pricing) and so we are going to move to Hyper V in that area.  Our Data Center VMware licenses are still supported until 2026, but we will be putting some time into getting up to speed with Hyper V on fail over clusters/SCVMM as well.

I think they will continue at the pace they have been going. Most of their innovation has been in the Azure space, which will continue to grow, but the “Cloud Everything” attitude is slowing down and “Cloud where it makes sense” is more popular right now. I just have too much data to make cloud affordable.

I think Microsoft have no choice but to keep trying to innovate in the security space, but they will most likely push to a subscription model for services like everything else as time goes on.

There are some things that they really SHOULD innovate though. The WSUS interface, AD Users and Computers searching, along with a few other things that have been the same forever that have so much potential. There are some old bugs as well that they have left behind for years too under certain conditions. 

I think until they redesign Windows Server from the ground up though, there will only be smaller features added as we go forward.  

I feel like Microsoft will continue to innovate, but it feels like Hyper-V and such’s real goal anymore is a gateway into Azure, or as a hybrid solution.  For instance, Exchange started off standalone on-premise, but moved to hybrid in conjunction with Microsoft 365, but now there is very little on-premise.  It’s windows right behind in the same motions?  Move it all to the cloud?  Although I feel like that’s a harder thing to do for existing orgs.  If you’re greenfield, then it makes more sense to start in the cloud.

Oh, and for SMB’s, I don’t expect it to expand much on-prem.  I feel like the innovation needed is going to be more in the enterprise space and those things just kinda filter on down to the SMB space.

What containerization services are you looking for? With Windows Server having WSLv2 and supporting both Windows and Linux containers, but also AKS-Hybrid enables the deployment of AKS Clusters on-prem. It currently supports AKS on Windows Server, Azure Stack HCI and in-preview vSphere - Azure Kubernetes Service (AKS) enabled by Azure Arc documentation | Microsoft Learn

Or is it more the supporting services like container repos?

Personally, I’d like to see Microsoft introduce a RestAPI for Windows Server. Powershell (Core) and SSH on Windows has improved interoperability with other systems, but realistically I’d like to have an API for like Performance Counters and Hyper-V rather than CIM and Powershell.

Yeah, I had forgot about WSLv2 and how you can run Kubernetes, etc. thanks for brining that up.

That would definitely be something interesting to see happen especially if they can make it work better than CIM/PS.