Unlocking Business Agility: Successfully Migrating Microsoft Workloads from Azure to AWS

Overview

A leading provider of time and attendance business solutions for small and mid-size companies recently underwent an acquisition, necessitating the consolidation of their IT infrastructure. As part of this strategic consolidation effort, the company needed to migrate 25 Virtual Machines (VMs) from Microsoft Azure to AWS. Caylent was engaged to deliver this migration with minimal downtime while maintaining network configurations, user access, and existing firewall rules. The project aimed to enhance operational efficiency while ensuring business continuity throughout the transition process.

Challenge

Following the acquisition, the client faced several significant challenges in consolidating their IT infrastructure. They needed to migrate 25 VMs from Azure to AWS while ensuring end users could continue using Microsoft Terminal Services Client for remote access—a critical requirement for their daily operations. The migration necessitated configuring Active Directory authentication for the instances to maintain secure user access without disrupting established workflows.

Maintaining security posture and network configurations during the transition presented another layer of complexity. The client's existing environment had specific firewall rules and security configurations that needed to be preserved in the new AWS environment. Additionally, the migration had to be completed with minimal disruption to business operations, as the client's time and attendance solutions were essential for their customers' daily operations.

The technical complexity was compounded by the need to synchronize systems during the transition period and ensure that all 25 VMs could be successfully migrated and cutover with minimal downtime. The client also required knowledge transfer to their team for ongoing management of the AWS environment, as their expertise was primarily in Azure.

Solution

Caylent developed a comprehensive migration strategy beginning with thorough discovery and planning. The team conducted an extensive inventory of all Azure VMs, applications, data, and configurations to establish a complete understanding of the environment. Security requirements and existing firewall rules were identified, network configurations and dependencies were mapped, and all VMs were assessed for AWS compatibility.

The architecture and design phase focused on creating an AWS environment that mirrored the Azure configurations while implementing AWS best practices. Amazon Elastic IP was utilized for static IP address allocation across all 25 instances, providing consistency in addressing. Security controls and compliance measures were designed in alignment with AWS best practices, and an implementation plan for Amazon Managed AD setup was created to support user authentication. The team also planned IAM roles and policies for secure remote access and translated existing firewall rules for the AWS environment.

Implementation included the setup of AWS infrastructure according to the design specifications. Secure VPN connections were established between Azure and AWS for data transfer, and AWS VPN was configured for end users to establish RDP connections to VM instances. Amazon Managed AD was set up, and existing users were exported and imported into the new Managed AD environment. The team then migrated VMs using AWS migration tools, implemented firewall rules within AWS, and configured IAM roles and policies for user access management.

The migration followed a phased approach starting with synchronization between source VMs and destination EC2 instances. All 25 VMs were synchronized to AWS for testing purposes, creating a parallel environment for validation before cutover. During the testing phase, the team conducted network performance and security testing while assisting the client with application testing from an infrastructure perspective. The cutover phase involved executing the final transfer of live data and workloads with careful monitoring of systems during the transition.

Results

The successful migration delivered significant benefits to the client's operations and infrastructure. Operational efficiency was enhanced through a consolidated IT infrastructure, reducing management overhead and streamlining processes across the newly combined organization. Business continuity was maintained with minimal disruption during migration, allowing the client to continue serving their customers without interruption.

User experience was preserved through familiar remote access methods, reducing the need for retraining and maintaining productivity. End users could continue using Microsoft Terminal Services Client to remote into the machines post-migration, just as they had done in the Azure environment. The migration also improved the security posture through implementation of AWS best practices and provided seamless authentication through properly configured Active Directory.

The AWS environment was configured with appropriate security controls, including data encryption during transit and at rest, AWS security groups mirroring Azure firewall rules, and AWS Key Management Service for key generation and management. AWS CloudTrail was enabled for governance, compliance, and operational auditing, providing improved visibility into the environment.

Comprehensive documentation was delivered for ongoing management, enabling the client's team to effectively operate in the new environment. Knowledge transfer sessions were conducted to ensure the client's team understood the operation of the infrastructure and could manage it moving forward. The client now benefits from a modernized environment that supports their business needs while providing a foundation for future growth and innovation.

By successfully migrating from Azure to AWS, the client achieved their goal of consolidating IT infrastructure following the acquisition, setting the stage for improved efficiency, reduced costs, and enhanced capabilities in their time and attendance business solutions.