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The Essential Guide to Windows Server on Azure

Due to the increasing security threats and costs of maintaining an on-premises Windows Server, shifting to the cloud is the first preference of every business. Microsoft Azure is the first choice when it comes to providing the best cloud service for your Windows Server. 

Many businesses are running the majority of their day-to-day operations using Windows Servers. Windows Servers have served the business world for more than 20 years, but with the introduction of cloud-based servers, businesses are being pulled towards cloud-based servers. The reasons behind this are mainly improved security, the ability to work remotely, and the increase in the speed of processes. Staying up to date with the advancements in the industry allows a business to stay ahead of its competitors. 

Azure is a cloud service by Microsoft that enables businesses to maximise their potential and shift their Windows Server to Azure cloud. Azure operates on Windows Server; hence it is easier and quicker for companies to adopt. It is important to learn, get help (if required) and research the cloud services as well as the needs of your company before opting for a cloud service.  

What Is Windows Server?

To support business-level data storage, communication, application, and management Microsoft has designed a framework that comprises multiple operating systems. Networking, stability, and security are the main reasons behind the development of the Windows Server. 

In addition to Windows Server, Microsoft has introduced hardware support and deployment technologies. Additionally, to support small-scale businesses, Stock Keeping Units (SKU) have been created. Windows Servers are kept up to date in accordance with the new business demands.

So far, Microsoft has launched three versions of Windows Servers. The latest version of Windows Server is focused on Cloud Computing, and the name of this version is “Windows Server 2022”.

The first version was launched in 2003, named Windows Server 2003, followed by Windows Server 2003 R2, and; it used multiple Windows XP features. The Windows Server 2003 incorporated improved DFTS capabilities, web services, network integration, and installation. 

The second server version, “Windows Server 2008 R2 and Windows Server 2008,” was empowered with an enhanced Firewall, additional .NET framework, security, and administration features. Kernel, memory, and filing systems were improved in this server version. The Windows Server 2008 R2 features were shared by Windows Vista. 

Why Azure Is the Best Cloud for Windows Server  

There are many cloud service providers offering their services, and Microsoft Azure is one of them. One might wonder why one should choose Azure to shift their Windows Server to the cloud. Microsoft Azure offers key advantages that make it the best cloud for Windows Servers. 

1. Cost-friendliness

Microsoft Azure is continuously working to provide the most cost-effective cloud service for your Microsoft workloads. Shifting to the cloud should be compatible with your bottom line; Azure Hybrid Benefit helps customers save money when they move to Azure. To cater to the cloud’s security issues while keeping the client’s budget in mind, Azure offers free extended security updates for Windows Server. 

Once you add up all associated costs, Azure for Windows Server becomes five times cheaper than AWS. In addition to all its features, Azure offers free cost management to all customers, which helps them optimise their spending. The money saved can be used to create new business value and better compete in the industry. 

2. Security 

The security and compliance services that Azure delivers are unmatched in the industry. You can run your most important applications and store your data using the Azure platform, in which Microsoft has invested $1 billion purely for security purposes. The global team of more than 3500 cybersecurity experts and security best practices of Azure make sure that your information is handled with the best security available. The unique features that distinguish Azure from other cloud services are:  

a. Your entire hybrid environment is monitored for threats and alerted by the Azure security centre.

b. Transparent privacy and security requirements are in place in compliance with Industry-leading certifications. 

c. Your governance process is made quicker by allowing you to set up blueprints that control compliance and policies in your network.

3. Consistency 

A business has multiple components, and not all of these are supposed to be shifted to the cloud. The Azure engineering team delivers hybrid functionalities that any other cloud service provider does not offer. Azure Active Directory can connect with on-premise Active Directory, which provides unhinged service for Azure as well as Office 365. 

Azure file sync offers bottomless storage for your on-premises Windows Server. Azure site recovery and backup allow you to protect your on-premises data and servers instantly. You can run different Azure services in your own data centre by using the Azure stack. 

Benefits of Azure for Windows Server Workloads 

Azure provides a well-managed and simplified experience for Windows Server. Microsoft Azure offers more than 200 services that you can use to modernise your Windows Server environment. You can use all of these services in your hybrid environment by extending them to your on-premises datacenter, or you can use them in Azure cloud as well. 

Azure Auto Manage will manage and configure your workloads automatically. There is no need to reboot your system to patch Windows Server on Azure. The Azure Virtual Desktop allows you to easily deploy a remote and secure desktop. 

Microsoft Defender for Cloud provides advanced threat protection and security management. Microsoft Sentinel, which is a cloud-native SIEM, secures your server workloads and encrypts your data when in use. SMB (Server Message Block) over QUIC (Quick UDP Internet Connections) provides a reliable, secure, and strong connection available between edge file servers and Windows Server on Azure.  

Migrate vs Extend: Windows Server on Azure  

On-premises servers can take up to weeks to set up, while you can easily configure a new Windows Server using Azure in minutes. Setting up multiple virtual machines or servers is very quick and easy with Azure. Round-the-clock support, constant health monitoring, and availability are ensured by Azure with data centres in 19 regions around the globe. Before starting to use Azure or any cloud services, you need to determine 

  • What applications in your Windows Server require to be transformed? 
  • Which applications can be shifted directly to the cloud? 
  • Which applications will benefit and which applications will not benefit from Azure integration? 

Once all these questions have been researched and answered, several options will be available for your applications and operating systems. 

  1. The first option will be to migrate the data and apps to the cloud or Azure platform. 
  2. The second option is to use new Azure services to extend the on-premise Windows Server environment to the cloud. 
  3. The third option can be to re-architect or redesign existing applications by using Azure “platform as a service” services.  

Migration and Modernization of Windows Server on Azure  

When you shift your existing applications systematically to Azure, it is called migration. Optimising and scaling applications using the Azure platform is referred to as modernization. Significant change management in the organisation that extends from people processes and technology is involved in cloud migration and modernization. There are three stages in migration; planning, implementation, and operation. 


This step involves assessing your environment, aligning the stakeholders, and defining your strategy toward migration. 

A good practice is to document and record your motivation behind migrating and modernising your Windows Server on Azure. This document must represent what business outcomes you want to achieve through the modernization and migration of Windows Server on Azure. You can involve IT managers, financial experts, and business owners to observe a smooth and faster migration.  

Azure offers multiple tools that can be used for planned migration and modernization of Windows Server or Azure. These tools include Cloud Economics on Azure, cloud migration eBook, documentation for developing a cloud adoption plan, and Azure TCO calculator. 


Training your IT departments and app development teams on how cloud techniques and migration tools operate can be very helpful for a smooth migration. It is vital to ensure that your workloads’ landing zones are preconfigured according to the best practices for Azure. This will allow you to easily use Azure migrate for cloud migration of your Windows Server on Azure with centralised tools. You can migrate a chunk of workload word loosened by an iterative process to migrate one workload at a time. 

You can increase your app innovation and agility by modernization at any stage. You can do it before, during, or after migrating your workloads from Windows Server to Azure. You can refactor or repackage your applications to connect easily with Azure. By re-architecting applications, you can break down bigger applications into microservices that can work together and enhance cloud scalability. To increase the lifespan or functionality of existing applications, you can use Azure Cloud Solutions to rebuild or re-create an app. 


Shifting your workloads from Windows Server to Azure gives you more control and visibility in the security infrastructure. In this stage, you familiarise yourself with being offered guidance and the tools provided by Azure. You can use real-time trends to add insights to keep a check on your workload performance to modernise your Windows Server on Azure. Disaster recovery solutions and cloud backup provided by Azure ensure that your workloads stay protected. 

Extend Windows Server on Azure with its Services  

Businesses prefer to work in a hybrid setting where they can keep working with their original data centre while sending some of the applications to the cloud. Azure enables businesses to work in their desired environment by improving their current data centres. In this way, businesses can retain the data centre environments and extend some of the functions to the cloud. 

Costs of maintaining a data centre, complexity of procedures, and compliance are enhanced by Azure site recovery and backup. Azure virtual machines help to increase the speed of the processes being run on the on-site machines. Seamless file sharing between local and remote users is possible by using Azure File Sync. 

All active directories that are on-premise or can be extended to Azure Active Directory, which helps you manage user access to on-premise and cloud information. You can archive on-premise data using Azure BLOB, which stores billions of objects in different tiers, Pending on how soon the data needs to be accessed. Azure allows you to archive inactive on-premise data to expand capacity automatically. 

Best Practices: Windows Server on Azure 

As Windows Server has reached the end of its support, continuing to use it can generate compliance issues with industry regulations like FEDRAMP, PCI DSS, GDPR, and others. Moreover, it can expose your business to security threats. Shifting Windows Server to Azure provides free extended security updates with no additional costs. Some best practices while converting Windows Server on Azure include assessment, planning, and preparation. 

Businesses need to determine and understand what workloads they have and what the purpose of that workload is. Where those workloads are installed and what do the workloads depend on, and which workloads are best suited to migrate to the cloud? While conducting an assessment following properties should be considered:

  1. Type of storage in Azure 
  2. Size of virtual machines  
  3. Running time for virtual machines 
  4. The category for the services 
  5. Target Azure location 

MAP for Microsoft assessment and planning toolkit can help you to make a full assessment of your workload. MAP is an easy-to-use agentless tool that helps in detailed Azure readiness assessment. 

Another best practice is to organise your workloads categorically. These categories include custom applications, Microsoft applications, workload running servers, and Microsoft partner applications.


Increasing competition in the business world demands new reforms. Shifting Windows Servers to Azure can be the first step ahead in the race with your competitors. You will decide which Azure service best suits your organisation, whether full cloud integration or a hybrid one. Windows Servers are safe and better performing when integrated with Azure Cloud Infrastructure.  

Want to automate your business, increase revenues migrate your workloads to the cloud? Wait no more; contact our Microsoft-certified cloud migration experts.

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