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As the end-of-life date for Windows Server 2008/2008 R2 approaches, should you stay on premises and migrate to Windows Server 2019, or is it time to make a change?
Has the cloud -- specifically Azure -- matured to the point you can hand over most of your on-premises identity infrastructure and other server-based workloads to Microsoft to manage? After all, no regular company profits from managing the identities of its employees, groups, passwords and the like. There are the usual arguments in favor of an Azure cloud migration: There is server hardware and software that may, in many cases, make sense to offload to a service provider to host and manage. The same logic applies to business email, and after several years, we see many organizations choosing to move entirely into the cloud or take a hybrid approach with some mailboxes hosted on Microsoft's platform and some left in the data center.
There are obviously other edge cases to consider, and every organization is different. But you can certainly use the January 2020 end of life for Windows Server 2008 to move a few critical workloads up to Azure. The feature sets in these cloud services can exceed the on-premises version of the workload, and Microsoft support handles most of the administrative work, such as security and troubleshooting.
Deciding between Active Directory versus Azure Active Directory
Active Directory (AD), the primary source of employee and identity information in most medium and large organizations around the globe, represents a substantial investment in corporate identity management. A significant number of technologies -- domain controller, read-only domain controller, distributed file system (DFS), Group Policy -- rely on on-premises AD.
While Microsoft's Azure AD is suitable for small businesses using Windows 10 along with device management and user management solutions, such as InTune, corporations with a fleet of thousands of laptops with software deployment through Group Policy, IntelliMirror and System Center cannot simply move to Azure AD. The feature set isn't there yet.
While it's clear Microsoft intends to make Azure AD functionally equivalent to on-premises AD, it still has a way to go. For most organizations with a substantial enough investment to care, they aren't close either.
Should I hold on to that on-premises file server?
The corporate file server has been the bedrock of the enterprise since the days of NetWare and 286 computers. Many companies still depend on them to hold gobs of data, and quite a few have DFS implementations on Windows Server 2003 still running.
The good news is that, as your client endpoints move to more modern OSes, like Windows 10, the Azure Files service can act as your cloud-based file server. You can keep a file server VM in each of your offices synced with a master file server instance running in Azure, and your clients can access the Azure Files service and shares directly over the internet just as they would address an internal file server.
Once you're on Windows 10, a newer Linux distribution or recent macOS versions, you can almost totally dismantle your internal file serving infrastructure if you want, and your Opex budget can handle it.
Is it time to switch to a cloud-based print server?
Despite the efforts of several vendors to move this infrastructure piece into the cloud, enterprise print servers are still required in almost all cases for end users to print from any number of devices at their disposal. Many times, this role is handed over to a device colocated on the printer so that a separate workload on a regular server isn't required.
Printing from a machine in the cloud to a locally installed printer requires printing over the remote desktop protocol or with a utility such as TSPrint and also requires network connectivity and service between your local network and the cloud. In short: Print servers will stay local for the foreseeable future.
Go with hosted email or stick with Exchange Server?
There will always be holdouts to cloud-based email, especially businesses in heavily regulated environments. For other organizations, it's not feasible to get the necessary bandwidth to have 100 users in a branch office run Outlook over the public internet. In those scenarios, there are technologies to ease this transition to hosted email on Exchange Online, such as storing attachments to OneDrive for Business to avoid transmitting them across slower links.
Apart from a few edge cases and super-large Exchange deployments with hundreds of thousands of mailboxes that would result in a ridiculous Opex budget impact, Exchange within Office 365 or hosted elsewhere is the way to go for many enterprises.
Is Remote Desktop Services on the way out?
Remote Desktop Services is a critical workload that isn't quite ready for the cloud for a variety of reasons. This may change as the Windows Virtual Desktop service matures, exits preview and reaches general availability, which is expected sometime in the second half of 2019.
Until all that happens, there is a hefty cost to run applications on VMs in the cloud with connectivity back to your on-premises network to remote into individual machines; it's expensive, and the performance is not optimal. Plus, there is a lot of manual configuration, and if you like the RD Web experience, there isn't a cloud equivalent.
For shops with many users who work remotely either intermittently or all the time and depend on Remote Desktop apps or machines in a virtual desktop infrastructure-type scenario, you still need your on-premises infrastructure.
Are web servers better off hosted in Azure?
If you run your web servers only on Windows Server 2008 or 2008 R2, then you might consider a switch to Azure App Service. Azure App Service graduated from hosting static webpages into a full-fledged platform for running .NET Web applications in ASP.NET and C#.
Azure App Service exceeds the web capabilities on those server platforms with advanced features, such as automatic instance scaling to meet spikes in demand and support for several popular databases as the back end for the web application. And, as a cloud service, Microsoft handles the patching and management for you. There's little advantage to hosting a website in your data center anymore when services as cheap, scalable and capable as Azure App Service are around.