Six Cloud Migration Challenges and How to Tackle Them

For a lot of organizations, cloud migration has become the centerpiece of their digital transformation. As everyone tries to stay competitive, agile, and cost-efficient, moving to the cloud often feels like the next logical step.

However, making that leap can feel overwhelming. The benefits are substantial, yet the path isn’t always straightforward. You might wonder: Are we ready? Are we prepared for the unexpected? The unknowns around security, cost, and integrations can create a sense of risk and even unease.
 

The good news? With the right knowledge and preparation, you can avoid many common pitfalls. Knowing what lies ahead gives you a big advantage—like getting the answers before the test.

Here, we’re highlighting 6 of the most common cloud migration challenges. By addressing these issues upfront, you’ll be ready to make your cloud migration smooth, secure, and successful. 

1. Inadequate Assessment and Planning 

The Challenge: The biggest mistake organizations make in cloud migration is jumping in without a thorough assessment and roadmap. Without a clear understanding of your existing infrastructure, data dependencies, and application needs, migration can lead to downtime, performance issues, and budget overruns. Failing to consider regulatory and compliance factors upfront can also introduce serious security and legal risks. 

Solution: The right starting point is a detailed migration assessment. This process goes beyond just identifying what you currently have—it uncovers how your systems, applications, and data interact. It pinpoints what can be migrated as-is, what may need re-platforming or refactoring, and where potential risks lie. 

With this clarity, you’ll gain a roadmap that outlines timelines, resource needs, and critical priorities for your migration. This step eliminates guesswork and ensures your move is efficient, cost-effective, and aligned with your business goals. 

By working with experts who specialize in migration assessments, you get a full view of potential challenges and opportunities. They provide tailored recommendations and actionable steps, helping you avoid disruptions and unexpected costs. A thorough assessment also ensures compliance and security are baked into the plan from the start, giving you peace of mind as you make the leap to the cloud.

2. Security and Compliance 

The Challenge: Moving any data to the cloud introduces new security challenges, especially as data moves beyond traditional firewalls. Compliance requirements around data storage, encryption, and access controls vary by industry, and a lack of clear security protocols can expose data to breaches and unauthorized access. 

Solution: Prioritize a security-first approach from day one. Set up multi-factor authentication, encryption protocols, and access management systems tailored to cloud environments. Work closely with your cloud provider to understand their shared responsibility model and how they address compliance requirements relevant to your industry. This often includes certifications for standards like GDPR, HIPAA, and SOC 2. 

In addition, implement regular monitoring and incident response protocols. Cloud-native security tools like Azure Security Center, AWS GuardDuty, and Google Cloud Armor can provide continuous monitoring and real-time threat detection to safeguard your data in the cloud. 

3. Hidden Costs 

The Challenge: Cloud migration often promises cost savings, but many organizations are surprised by the hidden costs that accumulate after migration. Usage-based pricing models can quickly add up, especially when resources aren’t optimized or managed correctly. For instance, organizations may see higher-than-expected fees for data storage, bandwidth, or even temporary burst capacity during peak usage. 

Solution: Conduct a thorough cost analysis before migrating, accounting for both initial and ongoing expenses. Use cloud cost calculators provided to estimate realistic expenses based on projected usage. After migration, consider a cloud cost management strategy that includes regular audits, identifying underused resources, and rightsizing your instances based on actual needs. 

Automation tools for cloud cost management will typically help track and control costs so you’re staying within budget while maximizing your cloud value. 

4. Integration and Dependencies 

The Challenge: Integrating cloud infrastructure with existing on-premises systems, applications, and databases can be a significant challenge, especially in complex IT environments. Legacy applications often have dependencies on specific servers, databases, or even other applications, making integrations tricky. Failing to account for these dependencies usually leads to failed migrations, disruptions, or performance issues. 

Solution: Identify all dependencies early (a migration assessment would be helpful here) and categorize applications based on their compatibility with the cloud. This should help guide decisions on which applications to migrate directly, which to re-platform, and which to retain on-premises. Leveraging hybrid or multi-cloud environments can also allow gradual integration for applications that may not be cloud-ready. 

Consider using API gateways and cloud integration platforms to bridge gaps between on-prem and cloud environments. Solutions like Azure Logic Apps, AWS AppFlow, and Google Cloud’s Apigee provide a way to link applications and data sources without disrupting operations. 

5. Skills Gap 

The Challenge: Cloud platforms require different skills than traditional on-prem IT environments. A lack of in-house expertise in areas like cloud architecture, security, and DevOps can slow down the migration process and increase the risk of misconfigurations, which then can lead to security vulnerabilities and inefficiencies. 

Solution: Invest in training or bring in skilled cloud professionals, either by hiring cloud-certified staff or by partnering with a managed cloud services provider. Many cloud providers offer extensive training programs—Azure, AWS, and Google Cloud all provide certification paths tailored to various roles, such as architects, developers, and administrators. Enrolling existing IT staff in these programs can help bridge skill gaps so your team is equipped to manage a cloud environment effectively. 

If in-house training isn’t feasible, consider working with a migration partner. These experts provide hands-on assistance and guidance for your team, and set up best practices to manage cloud environments. 

6. Multi-Cloud and Hybrid Environment Management 

The Challenge: Adopting a multi-cloud or hybrid cloud strategy offers flexibility and redundancy, but managing these environments can be easier said than done. Each cloud provider has unique tools, interfaces, and standards, making it challenging to maintain consistency, streamline processes, and stay secure across multiple platforms. 

Solution: Implement centralized management tools that provide a unified view of all cloud resources. Multi-cloud management platforms like Azure Arc allow administrators to monitor, secure, and optimize resources across diverse environments. Additionally, standardizing your security policies and configuration management across clouds can minimize misconfigurations and better ensure compliance. 

For a smoother multi-cloud or hybrid setup, you might want to adopt containerized applications with Kubernetes or use infrastructure-as-code (IaC) tools. These provide a consistent deployment and management experience, regardless of the underlying cloud provider, allowing you to maximize the benefits of a multi-cloud or hybrid approach without compromising on visibility or control. 

Final Cloud Migration Thoughts 

Migrating to the cloud is an exciting milestone for any business, but it’s natural to feel apprehensive about the unknowns. Each challenge—from planning and security to cost and multi-cloud management—represents a potential roadblock. But starting with a solid strategy, these challenges become manageable.

The key is preparation. By understanding what lies ahead, you can make better decisions, avoid most surprises, and set a steady course for cloud success. Cloud migration is a strategic investment in your organization’s future resilience and scalability. With the right approach, your cloud journey can be a smooth, cost-effective transformation that positions your business to thrive in a dynamic digital landscape.  

If you’re considering a move to the cloud let HBS guide your cloud transformation journey. Take the guesswork out of migrating by partnering with cloud migration experts.