Introduction

Have you ever looked at the weather, spotted a small cloud, and thought: “No big deal, this will be a smooth trip”, only to end up in a storm that turned everything upside down? Well, your cloud migration journey can feel exactly the same. That seemingly simple cloud can quickly become a thunderstorm if you’re not properly prepared. Understanding the challenges and knowing how to avoid pitfalls is the secret to turning this wild migration into a smooth journey. Trust me, you’ll want to be ready!

Cloud migration promises scalability, cost-efficiency, and innovation - but the journey isn’t without its challenges. From data transfer complexities to unexpected costs, even the simplest migrations face challenges. For large-scale projects, the stakes are even higher.

Fortunately, many of these challenges can be mitigated - or even avoided - through meticulous planning and adopting proven best practices, as outlined in our previous posts. In this post, that is part of our Cloud Migration series, we’ll see some common obstacles organizations face during migration and explore actionable strategies to overcome and prevent them.

Common Challenges:

• Data Transfer Complexity
• Cost Overruns (Plan vs. Real)
• Security and Compliance Concerns
• Skill Gaps
• Complexity in Large-Scale Projects

Challenges and Solutions with Proactive Strategies

Data Transfer Complexity

Transferring data can be slowed by limited bandwidth, compatibility issues, or the risk of data corruption. Large-scale migrations exacerbate these challenges, especially for businesses with diverse datasets and strict uptime requirements. Some businesses have only a short downtime window available, while others rely on a simple VPN connection. If you don’t plan the data transfer properly or don’t have a clear understanding of the data volume and available bandwidth, this will likely become the first major issue in your project.

Avoiding theses problems:

• Execute an effective assessment and ensure migration readiness.
• Plan migration pipelines early in the assessment stage (especially during data assessment).
• Conduct a bandwidth analysis to ensure your network can handle the load. Evaluate the options: VPN, Direct Link, or Device Transfer.
• Perform incremental migrations to reduce downtime.
• Implement robust data validation techniques to ensure accuracy.
• Implement a hybrid model during migration to keep critical systems operational.

A good assessment and plan can save you time and money, and will certainly help you avoid trouble!

Important services and tools that can help you:

• Leverage tools like AWS Snowball for offline data transfer to minimize network dependency.
• Use AWS DataSync to automate and accelerate repetitive tasks.
• Test migrations with smaller datasets before full-scale operations to identify bottlenecks.

Cost Overruns (Plan vs. Real)

One of the most common reasons people move to the cloud is cost reduction (I’ll share my honest opinion on this in a future post dedicated to cloud costs). However, the first issue, challenge, or problem (whatever you want to call it) is the high costs during the migration phase and even afterward.

I often see people miscalculating migration projects simply because they fail to consider costs during the migration phase, such as:

• The number of instances or services running more frequently and without savings plans.
• Data transfer costs (especially when transferring data out of other clouds).
• High storage volumes due to backups and temporary transfers.
• Local data center costs that continue to accrue throughout the project.

Migration projects often exceed budgets due to underestimating complexities, unexpected delays, or inefficient resource allocation.

Solution:

• Conduct detailed cost modeling using tools like AWS Pricing Calculator.
• Monitor expenses during migration with AWS Cost Explorer.
• Establish clear KPIs and regularly review progress against the budget.
• During the planning phase it's really important understand real current costs.
• Build contingency into your budget to account for unforeseen challenges.
• Engage stakeholders to align on objectives and avoid scope creep.

Tools and Services:

• Use AWS Cost Explorer and AWS Budgets for real-time expense tracking.
• Use AWS Pricing Calculator to simulate the costs.
• Optimize workloads post-migration by right-sizing resources.

Security and Compliance Concerns

Maintaining data security and meeting compliance standards during migration is critical, especially in regulated industries. Common risks include data exposure during transfer and post-migration misconfigurations.

How to Avoid It:

• Design a secure landing zone during the planning phase that adheres to your organization’s compliance requirements.
• Conduct risk assessments and compliance audits before and after migration.
• Implement cloud governance to ensure adherence to best practices and company compliance standards.
• Train your team on cloud security best practices.
• Engage compliance specialists to ensure adherence to relevant standards (e.g., HIPAA, GDPR).

Tools and Services:

• Encrypt all data in transit and at rest using AWS KMS.
• Use AWS Well-Architected Framework Security Pillar to review and enhance security practices.

Skill Gaps

Cloud is a fast-evolving technology, and it’s common to see companies without a trained team ready to manage cloud computing. It’s important to have a well-prepared internal team capable of supporting the migration and handling operations afterward. However, if you don’t have a highly skilled team, don’t worry - you can partner with a cloud services provider that has experienced professionals ready to execute your migration and support your operations.

Cloud migrations require expertise in areas like network architecture, application refactoring, and cloud-native tools. Lack of in-house skills can lead to delays and errors.

Solution

• Partner with an AWS Advanced Partner for specialized knowledge.
• Identify skill gaps early and build a training plan before initiating migration.
• Begin team training early - this can be incorporated into the partner's migration plan to speed up cloud adoption.
• Upskill your team using AWS Training and Certification programs.
• Invest in training for internal teams using AWS Skill Builder or certification programs.
• Start with smaller projects to allow the team to gain confidence before tackling complex workloads.

Complexity in Large-Scale Projects

"With great power comes great responsibility," as Uncle Ben would say when discussing the migration of complex or large workloads to the cloud. While challenges exist even with the simplest cloud migrations, they multiply significantly in complex scenarios. These include workloads requiring modernization, integration with multiple legacy systems, strict downtime windows, and diverse systems being moved simultaneously. And the complexity doesn't end there.

Managing interdependencies, multiple stakeholders, and performance requirements during massive migrations can be overwhelming.

I've been working primarily with SAP migrations, and SAP systems are typically complex with multiple legacy integrations and short downtime windows. This makes even simple lift & shift projects challenging due to the nature of the business.

How to handle with complex migration?

• The assessment phase is more critical than ever to ensure a thorough understanding of the current scenario and detailed planning of each phase.
• Use a phased migration strategy to reduce risk.
• Design a comprehensive architecture to validate each phase.
• Execute the AWS Well-Architected Framework before, during, and after migration.
• Track and review KPIs and milestones at each step.
• Implement strong project management practices.
• Engage specialists for each area and system being migrated.
• Break down the project into manageable phases and use tools like AWS Migration Hub for tracking progress.
• Monitor performance and dependencies in real-time using AWS CloudWatch.
• Create a detailed runbook to align teams and establish clear expectations.
• Designate a migration leader to maintain consistent communication and decision-making across teams.

Conclusion

Challenges are a natural part of any transformation, but they’re not insurmountable. With careful planning, a skilled team, and the right tools, even the most complex cloud migrations can succeed. By addressing these obstacles head-on, you’re not just moving to the cloud - you’re building a foundation for future innovation. In our next post, we’ll focus on securing your cloud environment and implementing governance strategies to maintain operational excellence. Stay tuned for more insights!

Blog series:

Blog post 1: Cloud Migration: What, Why, and Who Benefits

Blog post 2: Choosing the Right Path: 7 Cloud Migration Strategies (7R's)

Blog post 3: Every Phase Explained: An Overview of Successful Cloud Migration

References:

AWS Prescriptive Guidance - About the migration strategies

AWS Prescriptive Guidance - Phases of a Large Migration

AWS - How to Migrate

Numen Cloud Services

That’s all, let’s rock the future, see you soon!

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