Cloud migration involves transferring digital assets, services, databases, applications, and IT resources from on-premises infrastructure to cloud environments.
A well-executed cloud migration can reduce operational costs, improve scalability, enhance flexibility, and boost performance. Organizations can shift from capital-intensive infrastructure to more predictable pay-as-you-go expenses while scaling resources to match needs.
However, the path to digital transformation can be fraught with complexity. A poorly executed migration can lead to weeks of service disruption, significant revenue loss, security vulnerabilities, or compliance violations. Cloud migration requires careful coordination between legacy systems, cloud services, and cross-functional teams. Tools like the internal developer portal Cortex help engineering teams navigate this complexity by providing the visibility, standardization, and collaboration capabilities essential for successful cloud migrations. For example, Rapid7’s initiative to upgrade RDS instances shifted what would have taken months to less than 2 weeks.
We've distilled these insights from leading engineering teams into actionable, expert guidance to help you navigate your cloud journey successfully.
Common cloud migration challenges
Cloud migration extends far beyond the technical lift-and-shift of workloads. According to an Informatica study, 84% of cloud migrations exceed their budgets or timelines.
Engineering teams face pressure to balance technical implementation with organizational change management. Developers must refactor applications built for monolithic architectures to leverage the benefits of the cloud, and security and compliance requirements add layers of complexity that can derail even well-planned migrations. By anticipating common pitfalls, teams can develop targeted mitigation strategies that reduce risk and accelerate cloud adoption.
Lack of a clear migration strategy
Many organizations jump into cloud migration without defining clear objectives, success criteria, or a structured approach. Without a plan, teams will come up with their own approaches and can create new problems, such as choosing different technologies or language frameworks. This can create scope creep, extended timelines, and misaligned expectations among stakeholders. Without a clear strategy, teams often make ad-hoc decisions that compromise the migration's success.
Data security and compliance risks
Moving sensitive data to the cloud introduces potential security vulnerabilities and compliance concerns. Organizations must ensure data sovereignty, implement proper encryption, establish access controls, and maintain compliance with regulations like GDPR, HIPAA, or industry-specific standards. It’s important to figure out security early so data is secure. Failing to address these issues can result in data breaches, regulatory penalties, and reputational damage.
Downtime and business disruption
Migration activities can interrupt critical business operations, particularly for applications that must maintain high availability. Insufficient planning for downtime windows, inadequate failover mechanisms, or lack of rollback strategies can create disruptions beyond acceptable thresholds. This can disrupt user experience and business continuity, and the effects can extend past the initial outage by damaging trust in the product’s stability.
Overlooked application dependencies
Applications rarely exist in isolation. They often have complex dependencies on other services, databases, middleware, or third-party components. Failing to map these dependencies comprehensively before migration can lead to broken functionality, performance degradation, or complete service failures in the cloud environment.
Cost overruns and inefficiencies
Without proper cost modeling and optimization, cloud expenses can quickly go over budget. Many organizations experience "bill shock" after migration due to over-provisioning resources, inefficient architectures, or paying for unused services. Moving from buying hardware to paying monthly cloud bills demands new ways to control spending and be cost-efficient.
13 cloud migration best practices
Engineering teams that master cloud migrations follow tried-and-true practices that minimize risk, accelerate time-to-value, and prevent the technical debt that plagues hasty migrations. Here are actionable best practices to guide your cloud migration journey.
1. Define clear business objectives for cloud migration
Successful migrations align with specific business outcomes rather than pursuing cloud adoption for its own sake.
Instead of simply looking at metrics, focus on how a cloud migration aligns with your business goals and determine how to quantify its success–for instance, cost savings targets, performance improvements, or time-to-market metrics. Create dashboards that track migration progress against these business objectives, making the impact of your technical work visible to non-technical stakeholders.
2. Conduct a comprehensive inventory of IT assets
You can't migrate what you don't know exists. A thorough inventory serves as the foundation for migration planning and reveals hidden technical debt.
Use automated discovery tools to catalog all applications, databases, infrastructure components, and their interrelationships. Classify assets based on complexity, business criticality, compliance requirements, and technical characteristics, and include details like current resource utilization patterns, licensing constraints, ownership, and technology stacks.
3. Assess application dependencies and compatibility
Overlooked dependencies are the primary cause of migration failures, with unexpected outages and loss of functionality.
Map application dependencies using automated tools and manual verification. Create visual dependency graphs to identify interconnections between applications, services, and data flows. Evaluate each application's cloud compatibility, identifying components that require refactoring, replacement, or retirement before migration. Cortex's Service Catalog automatically maps and visualizes dependencies between services, databases, and infrastructure components, providing the comprehensive inventory needed for effective migration planning.
4. Select the appropriate cloud migration strategy
Applications require different migration approaches based on their architecture, business value, and technical constraints.
Apply the 6 Rs framework to categorize applications and determine the optimal migration strategy. Create decision trees or scorecards for each strategy that factor in technical debt, business value, and cloud readiness to make this process more objective and repeatable.
Rehost (lift and shift): Move applications to the cloud with minimal changes
Replatform (lift and optimize): Make targeted optimizations while migrating
Refactor/re-architect: Significantly modify applications to leverage cloud-native capabilities
Repurchase (drop and shop): Replace with cloud-native SaaS alternatives
Retire: Decommission applications no longer providing business value
Retain: Keep applications on-premises if they're not ready for migration
5. Develop a detailed cloud migration plan with timelines
A structured roadmap with clear phases, milestones, and dependencies helps keep you on track.
Break the migration into logical waves based on application groups with minimal dependencies. For each wave, define preparation tasks, migration activities, validation steps, and rollback procedures. Use techniques like feature flags and canary deployments to enable progressive migration with safe rollback capabilities. Establish realistic timelines that account for testing cycles, business approval processes, and potential remediation work. Cortex dashboards enable teams to track migration progress in real time, providing technical and business stakeholders with visibility into each application and service's status.
6. Implement robust security measures
Cloud environments introduce new security considerations around shared responsibility models, identity management, and network boundaries.
Establish a cloud architecture that addresses authentication, authorization, encryption, network security, and compliance requirements. Implement the principle of least privilege for all identities and resources. Set up continuous security monitoring and automated compliance checks. Incorporate security validation into your CI/CD pipelines and enforce architectural standards and governance guardrails while maintaining developer autonomy. It can also help develop security patterns and guardrails that development teams can easily adopt and ensure consistency across teams. Conduct regular security assessments and penetration testing to validate security controls.
7. Perform thorough testing in the cloud environment
Cloud environments behave differently from on-premises infrastructure, affecting performance, reliability, and functionality.
Establish a comprehensive testing strategy that includes functional validation, performance testing, security assessment, disaster recovery exercises, and business continuity verification. Create a staging environment that closely mirrors the production cloud configuration. Automate testing wherever possible, like in your CI/CD pipelines, to enable rapid validation cycles.
8. Utilize specialized tools to migrate to the cloud
The right cloud migration tools can accelerate the process, reduce errors, and provide valuable insights.
Evaluate and select tools for different phases of migration. Consider integrating some tools into your migration workflow to automate repetitive tasks and provide consistent governance.
Discovery and assessment: AppDynamics, CloudHealth, Flexera
Data migration: AWS Database Migration Service, Azure Data Factory, Striim
Application migration: CloudEndure, VMware HCX, Google Migrate for Compute Engine
Cost management: CloudHealth, Apptio, AWS Cost Explorer
9. Train and upskill IT staff
Cloud platforms require different skills than traditional infrastructure management, creating potential capability gaps.
Assess your team's current cloud capabilities and identify skill gaps. Develop a training plan that includes hands-on workshops and shadowing opportunities. The right tools will help share knowledge across teams. Cortex facilitates cross-team collaboration and knowledge sharing by documenting best practices, migration patterns, and service ownership in a centralized, searchable platform. Consider partnering those developing cloud skills with experienced cloud engineers for knowledge transfer.
10. Establish a post-migration monitoring and optimization plan
Continuous monitoring and optimization are essential for long-term success with cloud migration. Since initial capacity planning often involves making educated guesses and assumptions, it's critical to fine-tune and adjust as you gain more insights into your new architecture.
Implement distributed tracing and observability from day one in your cloud environment. Establish baselines for key metrics and set up alerting for deviations. Create dashboards that provide visibility into system health and cost efficiency. Develop regular optimization reviews to identify opportunities for improvement.
11. Use key metrics to measure migration success and continuous improvement
Quantifiable metrics can help provide an objective assessment of whether the migration was successful and guide ongoing optimization efforts.
Define and track key metrics across multiple dimensions to quantify improvements and identify areas for further optimization:
Technical: Availability, latency, error rates, deployment frequency
Financial: Cost per transaction, resource utilization, ROI
Operational: MTTR, incident frequency, automation coverage
Business: User satisfaction, feature delivery velocity, time-to-market
12. Ensure compliance with industry standards and implement advanced security protocols
Cloud environments introduce unique compliance and security considerations that you should address proactively.
Map regulatory requirements to specific cloud controls and configurations. Use policy-as-code tools like Open Policy Agent (OPA) or AWS Config to enforce compliance requirements programmatically. This enables developers to validate compliance during development rather than discovering issues in production. Develop security baselines for different types of workloads and environments.
13. Leverage IDPs to streamline collaboration and maintain engineering excellence
Many teams are involved in cloud migrations, and having a centralized knowledge base and standardized approaches makes the process much smoother.
Choose an IDP that serves as the single source of truth for migration documentation, best practices, reusable patterns, and service catalogs. Implement "golden paths" for common migration patterns—prescriptive, well-documented approaches that teams can follow to accelerate migration while ensuring consistency and compliance. Use the portal to enforce governance requirements while reducing friction for development teams.
Streamline your cloud migration with Cortex
IDPs like Cortex help teams with seamless cloud migration by providing the organizational infrastructure needed to support complex projects.
Cortex enables engineering teams to:
Catalog and document all services and their dependencies between services, databases, and infrastructure components in a single, searchable platform, creating the essential foundation for migration planning
Standardize migration patterns and approaches through scorecards, templates, and best practices, ensuring consistency across teams
Track migration progress in real-time with workflow automations and customizable dashboards that provide visibility into each application and service’s status to both technical and business stakeholders
Enforce architectural standards and governance guardrails while maintaining developer autonomy and velocity
Facilitate cross-team collaboration through shared knowledge bases and service ownership information
Organizations like Rapid7 have leveraged Cortex to accelerate their cloud migration initiatives while maintaining engineering excellence. Rapid7 streamlined the process, significantly reducing the time spent coordinating the migration and ensuring clear visibility into the remaining workload.
Amanda Jackson, Program Manager at Rapid7, says, "We had around 3,000 RDS instances that needed to be migrated across a variety of regions. With Cortex, we were able to spread out the lift to the appropriate domain owners to track down which RDS instances were left to be upgraded and which teams were responsible for the upgrade.”
Ready to supercharge your cloud migration? Book a demo with Cortex to see how our platform can help your engineering organization navigate cloud transformation successfully.
