Cloud Migration: Top Challenges and How to Overcome Them

Introduction to Cloud Migration

In the era of digital transformation, cloud computing has become the backbone of modern IT infrastructure. Organizations across industries are moving their applications, workloads, and data to the cloud to take the benefits like scalability, flexibility, cost-efficiency, and faster innovation cycles. But despite its advantages, the journey to the cloud is filled with challenges.

Cloud migration refers to the process of moving digital assets—data, applications, services—from on-premises or legacy systems to cloud-based infrastructure. It may also involve moving from one cloud provider to another, known as cloud-to-cloud migration.

According to market research report, over 85% of organizations will embrace a cloud-first principle by 2025. However, many still struggle due to lack of planning, security concerns, downtime, cost surprises, and skills gaps.

This blog explores the six most common cloud migration challenges and offers practical strategies to overcome them, ensuring a smooth and successful transition.

Challenge 1 – Lack of a Clear Migration Strategy

Why It Happens:

A rushed decision to “move to the cloud” without proper planning can lead to cost overruns, poor performance, and project failure. Businesses often underestimate the complexity of cloud migration and jump in without analysing their current infrastructure or aligning migration goals with business needs.

Solution:

Start with a cloud readiness assessment. Understand your current architecture and decide what to move, how, and when.  You can use MRA (Migration Readiness Assessment), Migration evaluator, CART (Cloud adaptation Readiness Tool) at the initial stage of migration.

Also, define KPIs to measure success—performance, cost savings, or user experience.

Example: A retail company rehosting its ERP system might benefit from short-term gains, but if it doesn’t optimize for cloud capabilities, long-term costs may increase.

Challenge 2 – Security & Compliance

Why It Happens

Organizations handling sensitive data (healthcare, finance) fear losing control when their data resides in a third-party environment. Compliance regulations like GDPR, HIPAA, and PCI-DSS further complicate the migration process.

Solution:

Choose a cloud provider with strong security certifications (e.g., ISO 27001, SOC 2).

Encrypt all data—in transit and at rest.

Implement Identity and Access Management (IAM) policies and multi-factor authentication (MFA).

Use cloud-native security tools for real-time threat detection.

Tip: Regularly audit your cloud environment and map controls to compliance frameworks.

Challenge 3: Downtime and Service Disruption

Why It Happens

uring migration, system unavailability or failures can interrupt business operations, leading to revenue loss or customer dissatisfaction.

Solution:

Migrate in phases, starting with low-risk applications.

Use real-time replication tools to sync data during the move.

Implement blue-green deployments or canary testing to reduce disruption.

Always have a rollback plan to revert changes if needed.

Example: A fintech firm migrating customer account services should use dual deployment environments to switch traffic only after full testing.

Challenge 4: Cost Management

Why It Happens

Cloud pricing can be deceptively complex. Hidden costs—data egress, underutilized instances, or misconfigured services—can lead to overspending.

Solution:

Estimate costs with cloud pricing calculators before starting.

Monitor with tools like AWS Cost Explorer or Azure Cost Management.

Set budget alerts and enable autoscaling to match demand.

Use reserved instances or spot instances for predictable workloads.

Pro Tip: Tag all resources to track departmental or project-based usage.

Challenge 5: Skills Gap in the Team

Why It Happens

Legacy IT teams may lack expertise in cloud platforms, networking, DevOps, or cloud security—slowing down the migration or causing errors.

Solution:

Train your teams using platforms like AWS Training, Microsoft Learn, or Google Cloud Skills Boost.

Consider hiring certified cloud professionals.

Leverage managed service providers (MSPs) for complex projects.

Foster a DevOps culture to streamline collaboration.

Stat: According to a report by Flexera, 73% of organizations cite “lack of resources/expertise” as a top cloud challenge.

Challenge 6: Application Compatibility & Legacy Systems

Why It Happens:

Some legacy apps weren’t designed for the cloud. They may depend on outdated libraries, have complex integrations, or rely on low-latency local networks.

Solution:

Categorize applications by cloud-readiness.

Consider containerization with Docker or orchestration via Kubernetes.

Use cloud-native modernization tools (e.g., Azure App Service, AWS Lambda).

Where needed, replace with SaaS alternatives like Salesforce or Office 365.

Example: Instead of migrating an old CRM system, many companies opt for cloud-native SaaS like HubSpot or Zoho.

Common Migration Strategies

1. Rehosting (lift and shift) – Moving apps without changes. This can be done using MGN (Application Migration) service in AWS.
2. Refactoring – Making slight modifications to optimize for the cloud
3. Replatform – Make a few cloud optimizations to achieve a tangible benefit. You will not change the core architecture of the application. For example, reduce the amount of time you spend managing database instances by migrating to a database-as-a-service platform such as Amazon Relational Database Service (Amazon RDS) or migrating your application to a fully managed platform, such as AWS Elastic Beanstalk.
4. Repurchase– Moving to SaaS alternatives. For example, move from a customer relationship management (CRM) to Salesforce.com, an HR system to Workday, or a content management system (CMS) to Drupal.
5. Relocate – Move vSphere-based applications to AWS without application changes.
6. Retain (referred to as revisit) – Keep applications that are critical for the business, but that require major refactoring before they can be migrated. You can revisit all applications that fall into this category at a later point in time.
7. Retire – Remove applications that are no longer needed.

Final Thoughts: A Smart Cloud Journey

Cloud migration is more than just a technical shift—it’s a strategic transformation. With a structured approach, strong leadership, and a clear focus on business outcomes, organizations can navigate migration challenges effectively. Follow 3 step journey recommended by AWS – Access, Mobilize, Migrate and Modernize.

Key takeaways:

Start with a well-defined plan.

Prioritize security and compliance.

Manage costs proactively.

Start with small scale migration and then with experience start large scale migration.

Upskill your team and leverage automation.

Treat migration as an ongoing process, not a one-time event.

Done right, cloud migration opens doors to innovation, agility, and a resilient digital future.

About CloudThat

CloudThat is a leading provider of Cloud Training and Consulting services with a global presence in India, the USA, Asia, Europe, and Africa. Specializing in AWS, Microsoft Azure, GCP, VMware, Databricks, and more, the company serves mid-market and enterprise clients, offering comprehensive expertise in Cloud Migration, Data Platforms, DevOps, IoT, AI/ML, and more.

CloudThat is the first Indian Company to win the prestigious Microsoft Partner 2024 Award and is recognized as a top-tier partner with AWS and Microsoft, including the prestigious ‘Think Big’ partner award from AWS and the Microsoft Superstars FY 2023 award in Asia & India. Having trained 650k+ professionals in 500+ cloud certifications and completed 300+ consulting projects globally, CloudThat is an official AWS Advanced Consulting Partner, Microsoft Gold Partner, AWS Training Partner, AWS Migration Partner, AWS Data and Analytics Partner, AWS DevOps Competency Partner, AWS GenAI Competency Partner, Amazon QuickSight Service Delivery Partner, Amazon EKS Service Delivery Partner,  AWS Microsoft Workload Partners, Amazon EC2 Service Delivery Partner, Amazon ECS Service Delivery Partner, AWS Glue Service Delivery Partner, Amazon Redshift Service Delivery Partner, AWS Control Tower Service Delivery Partner, AWS WAF Service Delivery Partner, Amazon CloudFront, Amazon OpenSearch, AWS DMS, AWS Systems Manager, Amazon RDS, and many more.