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Common Challenges in On-Premise to Azure Cloud Migration and How to Solve Them

Author: Olivia Johnson
by Olivia Johnson
Posted: Jan 24, 2026

If you are running a company, you know that switching to cloud infrastructure is no longer an option. That's why enterprises are increasingly moving away from restrictive premises data centers. They want greater agility and cost optimization. All of that is found in cloud computing. And among all the platforms in the market, Microsoft's Azure manages to stand out. But moving from an on-premises environment to the Azure cloud is still rarely a straightforward lift and shift operation. The process is complex, involving numerous factors such as legacy system dependencies and security integration. The destination decidedly has obvious advantages, yet the journey is frequently fraught with challenges.

You see, you can't navigate this transition solely based on technical skill. This migration demands meticulous planning and a strategic approach. So in this blog, I will discuss some of the more common on premise to Azure migration challenges and how to deal with them.

On Premise to Azure: Key Migration Challenges You Are Likely To Face

Migrating from on-premises systems to Azure isn’t just a technical shift, it’s a strategic challenge. Organizations often face hurdles like application complexity, security gaps, network latency, and cost overruns. Understanding these issues upfront is critical to ensure a smooth transition and unlock the full potential of Azure’s cloud capabilities.

Let’s discuss the key migration challenges;

  • Application complexity: Legacy applications are frequently tightly coupled to the specific configuration of on premises hardware and OS, with complex dependencies. This inherent complexity precludes a simple cloud migration, necessitating significant cost and effort for application modifications, etc. to ensure functional compatibility in the Azure environment. The first step towards overcoming this is to conduct a thorough application discovery and assessment.
  • Security risks: Migration from an on-premises environment poses significant risks because the existing perimeter-based security model does not seamlessly translate to the cloud's shared responsibility model. So, organizations must first gain a clear understanding of the Shared Responsibility Model. This involves explicitly defining which security tasks remain under the internal team's control versus those managed by Microsoft.
  • Network performance issues: During both the active migration phase and the initial post migration operation, the required connectivity between the existing on premises systems and the new Azure infrastructure can be severely hampered. By what? That would be increased latency, limited bandwidth, and so on. To ensure consistent performance, Azure ExpressRoute is the primary option. It provides guaranteed higher bandwidth, low latency, and other benefits for fast data transfers. It also supports business critical hybrid operations.
  • Budget overruns: A common mistake in cloud migration planning is underestimating the TCO. The most effective way to control costs is to use "right size" resources. That means using performance data and the Azure Migrate Assessment tool before migrating. This is meant to determine the true utilization of on premises VMs and databases. Workloads with predictable usage patterns can also help with cost savings through Azure Reserved VM Instances or the Azure Savings Plan for Compute. This leads to significant discounts over the standard pay as you go rates.
  • Service interruptions: A cutover during a migration is vulnerable to downtime. This is due to inadequate planning or the unexpected discovery of unknown app dependencies. Service interruptions can be easily mitigated by setting up a dedicated testing environment within Azure. And don't forget the backup and recovery procedures must also be thoroughly tested.
  • Skill shortages: The disparity among the existing IT teams is a major impediment to smooth and rapid migration. I speak about their skills, of course. The primary solution is to invest in team development through targeted training and certification programs focused on Azure. Prioritizing automation via IaC tools can result in increased long-term efficiency and less reliance on individual experts.
  • Performance problems: Once you have successfully migrated to Azure, apps may perform noticeably slower than they did with premises infrastructure. The first step is to establish and maintain performance benchmarks taken prior to migration. For database specific slowness, leverage Azure's database assessment and tuning tools to identify and optimize any inefficient SQL queries or stored procedures.
  • Final WordsMigrating to Azure offers unmatched scalability and efficiency, but success depends on preparation. By addressing application complexity, security, performance, and cost challenges proactively, businesses can ensure a seamless transition. With the right strategy and skilled teams, Azure becomes a powerful enabler of innovation and long-term growth. Are you ready to kick off your on premise to Azure migration? Then you must find and onboard a trusted service provider ASAP.

    About the Author

    Olivia Johnson is a technical writer, love to share stuffs related to technology & development.

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    Author: Olivia Johnson

    Olivia Johnson

    Member since: May 27, 2018
    Published articles: 62

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