The 6 Rs of cloud migration—Rehost, Replatform, Refactor, Repurchase, Retire, and Retain—form a strategic framework that helps organizations decide how to transition applications to the cloud. However, the effectiveness of the 6 Rs depends entirely on how accurately they are applied. Too often, businesses make critical mistakes by rushing, oversimplifying, or misclassifying workloads without proper evaluation.
These mistakes aren’t just technical. They result in overspending, unplanned downtime, compliance gaps, and lost ROI. Whether it’s rehosting a system that should be refactored or retiring an app with hidden dependencies, the consequences can derail an entire transformation project.
This guide outlines the 10 most common and costly mistakes businesses make when applying the 6 Rs, drawn from real-world consulting experience. Each section includes:
- Why the mistake happens
- The business and technical impact
- How to prevent or fix it
Whether you’re a CIO, IT manager, or infrastructure lead, understanding these pitfalls will help you build a migration strategy that is technically sound, business-aligned, and future-proof.
1. Skipping the Strategy Phase Entirely
Why It Happens
Many businesses are driven by deadlines, budget pressures, or vendor incentives that push them to “just get to the cloud.” As a result, they bypass the strategy phase—moving forward without a complete workload inventory, compliance review, or R-path assignment.
In some cases, IT leads assume all workloads can be lifted and shifted (Rehost), or believe that migrating everything to SaaS (Repurchase) will be inherently cheaper. Without structured planning, these assumptions lead to misalignment between system requirements and cloud architecture.
Impact
Skipping strategic classification results in:
- Downtime from incompatible deployments
- Missed dependencies between systems or databases
- Overpaying for underutilized cloud resources
- Loss of stakeholder trust when applications break or underperform post-migration
Worse, once workloads are deployed in cloud with the wrong R path, rework can be more complex and costly than doing it right the first time.
Fix: Run a Migration Readiness Assessment
Before applying any R strategy, CitySource conducts a structured cloud migration readiness assessment, which includes:
- Workload inventory
- Technical architecture review
- Application criticality scoring
- Compliance classification
- Recommended R-path assignment with justification
This ensures that each system is matched to the correct cloud migration approach—not just the fastest or most popular one.
Our End-to-End Cloud Migration Strategy includes full strategy planning, risk analysis, and support continuity—before migration begins.
2. Rehosting Systems That Actually Require Refactoring
Why It Happens
Rehosting—often called “lift-and-shift”—is the fastest and least technically demanding of the 6 Rs. It involves moving workloads to the cloud without modifying code or architecture. This makes it attractive for IT departments under pressure to migrate quickly or demonstrate early wins.
However, Rehost is frequently applied to modern, high-impact systems that are better suited for Refactor—a strategy involving code restructuring to optimize for cloud-native features like scalability, resiliency, and API-first design.
This misapplication usually happens when:
- Stakeholders prioritize speed over functionality
- There is insufficient architectural analysis
- The application seems cloud-ready “on the surface”
- DevOps maturity is lacking, so teams avoid transformation
What’s missed is that modern applications—especially customer-facing platforms, eCommerce systems, or real-time analytics engines—require auto-scaling, containerization, and distributed architecture that Rehost cannot deliver.
Impact
Rehosting systems that need refactoring results in:
- Performance bottlenecks under high load
- Higher long-term cloud costs due to inefficient compute usage
- Inability to implement CI/CD pipelines or automation
- Difficulty in adding features or scaling environments
- Loss of competitive agility in delivering digital services
Instead of unlocking cloud-native benefits, the organization replicates legacy limitations in a cloud-hosted environment.
Fix: Use Architectural Scoring to Identify Refactor Candidates
At CitySource Solutions, we use an R-path scoring framework to determine when refactoring is not only viable but necessary. We evaluate:
- Application modularity
- Deployment frequency
- Scalability needs
- User concurrency
- Integration depth (APIs, third-party systems)
If a system is central to growth, product delivery, or digital transformation, and exhibits high change velocity, Refactor becomes the logical choice—even if it adds initial complexity.
Our engineers support clients in building containerized refactored applications using tools like Kubernetes, AWS ECS, or Azure Functions—allowing for automation, rapid scaling, and reduced TCO.
See the full 6 Rs Cloud Migration Strategy Breakdown to compare paths by risk, cost, and long-term value.
3. Retiring Systems With Hidden Dependencies
Why It Happens
Retirement is one of the most overlooked Rs in the migration framework. Organizations often discover legacy applications during their cloud readiness inventory and decide to retire them—assuming these systems are outdated, unused, or irrelevant.
However, many of these so-called “obsolete” systems continue to serve critical background functions, such as:
- Scheduled batch jobs or data exports
- API endpoints used by downstream applications
- Embedded authentication or user access flows
- Legacy data sources referenced in reporting dashboards
Without deep dependency analysis, these systems are retired prematurely—causing cascading failures across the IT environment.
The problem is worsened when:
- System logs are incomplete or disabled
- Only a few users or departments rely on the tool
- Documentation is outdated or nonexistent
- The application has no front-end but powers back-end automation
Impact
Incorrectly retiring systems can lead to:
- Broken integrations and failed transactions
- Loss of historical or regulatory data
- Unplanned downtime in adjacent systems
- Support team escalation and emergency fixes
- Compliance breaches if records are deleted without audit review
These errors often surface post-migration, when the retired app was quietly powering finance exports, CRM syncs, or legal record retrievals.
Fix: Map System Dependencies Before Applying “Retire”
CitySource applies a dependency discovery process as part of any Retire recommendation. This includes:
- Port scanning and traffic analysis
- Cross-system integration checks
- Application log review and usage history audit
- Stakeholder interviews with department owners
Only once a system is confirmed to have no downstream reliance, and all data is archived in accordance with policy (e.g., FINRA 17a-4, HIPAA retention), is it approved for decommissioning.
We also provide structured retirement runbooks, outlining:
- Data extraction
- Metadata export
- Legal hold application
- Access revocation and audit trail preservation
4. Choosing SaaS Without Reviewing Compliance
Why It Happens
The Repurchase strategy—replacing legacy tools with SaaS platforms—is appealing for businesses seeking reduced maintenance, improved UX, and predictable pricing. Tools like Salesforce, Microsoft 365, Google Workspace, and industry-specific SaaS products promise instant modernization.
However, many organizations move forward with SaaS repurchase decisions without validating vendor compliance posture, especially in highly regulated environments like:
- Healthcare (HIPAA, HITECH)
- Financial Services (FINRA, SOX, GLBA)
- Legal and Government (CJIS, NYDFS, FISMA)
Often, SaaS vendors offer standard security certifications (e.g., SOC 2, ISO 27001), but lack industry-specific guarantees or data residency controls required by enterprise customers.
Impact
Unverified SaaS adoption leads to:
- Audit violations and regulatory penalties
- Data residency conflicts (e.g., storing U.S. PII in foreign data centers)
- Inability to pass vendor risk assessments or security reviews
- Forced rollback to legacy systems during compliance remediation
Many IT teams assume SaaS = secure, but not all SaaS platforms align with internal governance, especially in hybrid or multi-cloud environments.
Fix: Run SaaS Compliance Mapping Before Repurchase
Before recommending Repurchase, CitySource performs a SaaS Compliance Fit Analysis based on your industry, location, and policy obligations.
We validate:
- HIPAA/HITECH attestations for healthcare
- SOC 2 Type II and PCI-DSS scope for finance
- NYDFS Part 500 and data encryption standards
- Data retention timelines and logging capabilities
When SaaS platforms meet 80% of the client’s compliance needs but fall short in a few critical areas, we advise replatforming or hybrid retention instead—keeping core sensitive systems in a secure private cloud while adopting SaaS for front-end tools.
Our cybersecurity monitoring also integrates with third-party SaaS platforms to ensure threat visibility, configuration hardening, and ongoing access control.
5. Underestimating Replatforming Complexity
Why It Happens
Replatforming is often misunderstood as a “safe middle ground” between Rehost and Refactor. It typically involves making minor adjustments to operating systems, middleware, or database engines to gain performance or scalability benefits—without rewriting application code.
Because it sounds low-risk, many businesses move forward with replatforming without conducting compatibility, performance, or dependency testing. This is especially true when migrating:
- Legacy Windows Server apps
- On-prem SQL Server or Oracle DBs
- Applications with hardcoded paths or proprietary DLLs
- Systems dependent on internal authentication services like Active Directory
Executives often greenlight replatforming to accelerate time-to-cloud, assuming it’s a simple OS or DB upgrade. The reality is that even “small” infrastructure changes can break critical business functions if not scoped correctly.
Impact
Poorly executed replatforming results in:
- Authentication or session timeout failures
- Service crashes due to OS-level conflicts
- Data corruption from incompatible DB schema handling
- Broken integrations with legacy API gateways
- Rollback complexity during live migration events
These outcomes not only stall migration progress—they erode trust from internal teams, customers, and business stakeholders.
Fix: Validate Compatibility and Dependencies Pre-Migration
Before approving any Replatform recommendation, CitySource performs a full environmental compatibility and risk audit, including:
- OS-level dependency tracing
- Database schema + stored procedure testing
- Load and concurrency simulation in staging
- SSO, Active Directory, and permission flow verification
- Containerization feasibility for Linux-based workloads
If a system lacks documentation or supportability, we often recommend starting with Rehost and gradually evolve to Replatform or Refactor after infrastructure stabilization.
We also deploy pilot environments where replatformed workloads can be validated against real-world business use before go-live—ensuring service continuity and user confidence.
6. Applying the Same R to Every Workload
Why It Happens
Organizations often seek standardization for simplicity—choosing one R strategy (usually Rehost or Repurchase) and applying it across the board. This usually stems from executive pressure to accelerate timelines, reduce decision fatigue, or align with a preferred vendor platform.
In reality, every application has unique:
- Compliance requirements
- Licensing conditions
- Technical dependencies
- Business criticality
- Modernization potential
For example, rehosting a non-critical file server might be efficient. But rehosting a real-time order processing system—or repurchasing a tightly integrated CRM—introduces risk, loss of functionality, and cost inefficiency.
Impact
Over-standardizing R strategy leads to:
- Misallocated budgets (refactoring low-value apps, or underinvesting in strategic systems)
- Feature regression due to SaaS limitations
- Over-provisioned resources from lift-and-shift inefficiencies
- Data fragmentation across inconsistent platforms
- Project failure in hybrid environments
Standardization for the sake of simplicity often creates long-term complexity.
Fix: Assign Rs Based on Workload Scoring
CitySource applies individual workload evaluation across six scoring criteria:
| Dimension | Scoring Purpose |
|---|---|
| Business value | Core, supporting, or obsolete? |
| Risk classification | Compliance, SLA impact, data residency |
| Technical debt | Legacy code, unsupported versions |
| Integration depth | How many systems rely on it? |
| Scaling requirements | Static load or dynamic user base? |
| Modernization potential | Refactor candidate or stable legacy? |
We classify systems one by one, then assign appropriate Rs across the migration wave plan.
7. Ignoring Licensing and Cost Overlap After Repurchase
Why It Happens
Repurchase—replacing software with SaaS—is often justified as a cost-cutting measure. But businesses frequently neglect to fully decommission legacy licenses, tools, and maintenance contracts after adopting new cloud platforms.
This is especially common when:
- SaaS is purchased before legacy contracts expire
- Departments use overlapping tools (e.g., Teams and Zoom, Dropbox and SharePoint)
- IT fails to disable auto-renewals or reclaim on-prem licenses
- End-users quietly continue using old systems in parallel
Over time, this results in duplicate spending and shadow IT, undermining the intended ROI of migration.
Impact
Unmanaged post-repurchase environments create:
- Budget drain from overlapping vendor fees
- Conflicting user workflows across old and new systems
- Support complexity from multiple platforms
- Security risk if legacy apps remain exposed or unpatched
- Audit failure due to untracked software use
Organizations migrating to cloud often reduce CapEx, but unintentionally increase OpEx through license sprawl.
Fix: Decommission and Rationalize Concurrently
CitySource creates a Repurchase Retirement Plan as part of our SaaS transition model. This includes:
- License audit and cancellation timeline
- SaaS usage monitoring for adoption and coverage
- Legacy system access restriction policies
- Contract review for early termination clauses
- Communication strategy for end-user adoption and migration
We also monitor new SaaS platforms through our Managed IT Support stack—tracking logins, update cycles, and configuration hygiene to keep tools compliant and optimized.
8. No Retention Plan for Retired Systems
Why It Happens
When teams identify systems for Retirement, they often treat decommissioning as deletion—especially if the system is old, undocumented, or deemed non-critical. The assumption is that “we’re not using it, so we can remove it.”
However, retired systems often contain records, logs, or audit trails needed for:
- Regulatory compliance (HIPAA, FINRA, GDPR)
- Historical analytics
- Internal investigations or audits
- Legal hold obligations
The lack of a retention policy or archival plan leads to irreversible data loss, audit failures, and security gaps.
Impact
Improper system retirement leads to:
Data privacy violations if old records are deleted or mishandled
Loss of business-critical historical data
Non-compliance with legal recordkeeping rules
Forensic blind spots during breach investigations
Litigation risk from failure to maintain discoverable records
Fix: Apply Structured Data Lifecycle Management
CitySource never retires a system until the following are completed:
- Retention review: Match data against regulatory retention mandates
- Legal hold application: Apply holds to specific data classes or users
- Metadata extraction: Maintain searchability post-system shutdown
- Access isolation: Archive to secure cold storage with access logging
- Documentation: Log what was retired, where it resides, and how to retrieve
Retirement ≠ deletion. We treat it as a controlled transition, not a purge.
9. Failing to Include Stakeholders in Strategy Selection
Why It Happens
IT leaders often drive cloud projects based on infrastructure readiness—but neglect to include business users, compliance leads, finance, or legal in the R-assignment process. This causes blind spots in:
- Operational workflows
- SLAs and customer expectations
- Regulatory considerations
- Budget constraints and licensing implications
When stakeholders are excluded, critical input is missed—and buy-in is lost.
Impact
Siloed decision-making creates:
- Rejected SaaS rollouts due to missing functionality
- Compliance conflicts from unacknowledged data handling needs
- Unbudgeted costs when teams continue using legacy apps
- Loss of confidence in IT ownership of transformation initiatives
Fix: Build a Cross-Functional Migration Working Group
CitySource establishes a Cloud Migration Governance Framework at project kickoff, including:
- IT and engineering leaders
- Application owners
- Security, compliance, and GRC stakeholders
- Finance for TCO and license overlap
- Executive sponsor or transformation lead
Each R-assignment is validated across technical fit, business value, and operational impact, with full visibility.
10. Launching Without Post-Migration Monitoring or Support
Why It Happens
After migration go-live, IT teams often shift focus to other priorities—assuming the “cloud will manage itself.” But without structured monitoring and support, cloud environments drift from configuration, leaving:
- Vulnerabilities unpatched
- Costs unmanaged
- Users unsupported
- Performance unoptimized
Cloud-native doesn’t mean cloud-maintained.
Impact
Lack of post-migration support causes:
- Cost creep from unused or overprovisioned resources
- Unmonitored access permissions and security gaps
- High volume of unresolved user tickets
- Lack of visibility into uptime or SLA violations
Cloud without operations = infrastructure debt.
Fix: Implement Ongoing Monitoring and Helpdesk Support
CitySource provides full-stack managed cloud support, including:
- 24/7 infrastructure monitoring
- Automated patching and OS updates
- Real-time alerting and anomaly detection
- Helpdesk for end-user issue resolution
- Performance tuning based on usage metrics
Our Managed Support and Helpdesk Services ensure your cloud stays optimized, secured, and aligned with business operations—long after migration is complete.
Conclusion: Prevent the Most Expensive Cloud Migration Mistakes Before You Commit
Cloud migration is not just about moving infrastructure—it’s about making strategic decisions that affect business continuity, cost control, and compliance long after deployment. Applying the 6 Rs of cloud migration without structured evaluation often results in rework, unplanned costs, missed objectives, and operational downtime.
By avoiding these ten critical mistakes—misclassifying workloads, ignoring dependencies, skipping compliance mapping, and failing to engage stakeholders—your organization can achieve a smooth, scalable, and secure transition to cloud infrastructure.
At CitySource Solutions, we help you make the right R decisions the first time through technical scoring, stakeholder validation, compliance modeling, and full-stack support from planning to optimization.
Get Your Cloud Migration Strategy Right With CitySource
Don’t risk your business-critical systems with poor planning or misaligned strategy. At CitySource Solutions, we align every R strategy to business goals, technical fit, and regulatory requirements—backed by our expert engineers and real-world experience.
1- Application scoring and dependency mapping
2- R-strategy validation and cross-functional planning
3- End-to-end migration execution
4- Post-migration monitoring and helpdesk support
📞 Call us at (914) 815-9000
📧 Contact our cloud consultants today
FAQ: 6 Rs Cloud Migration Mistakes
What’s the most common mistake in applying the 6 Rs?
Assigning the same R strategy to all workloads—typically Rehost or Repurchase—without evaluating technical complexity, compliance impact, or business value.
Can we change our R strategy after migration?
Yes, but it introduces risk, downtime, and cost. Refactoring a Rehosted system later is more complex than starting with the correct approach.
How do I know if we selected the wrong migration strategy?
Signs include increased post-migration support tickets, performance issues, security misconfigurations, and systems failing to meet business or compliance needs.
Who should be involved in migration strategy selection?
IT leaders, infrastructure teams, compliance officers, application owners, and finance stakeholders. R decisions affect more than infrastructure—they impact business operations.
