10 Challenges in Cloud Migration and How to Solve Them

Most teams brace for the wrong risk when they plan a move to the cloud. They worry about the mechanics of copying files, but the projects that actually go sideways fail for less obvious reasons: the wrong workload landed in the wrong environment, a dependency nobody mapped broke on cutover day, the ongoing bill came in nowhere near the estimate, or nobody owned the environment once the migration team went home. These are the real cloud migration challenges, and they show up long before or long after the data transfer itself.

The scale of the problem is documented. Application dependencies were the single biggest migration obstacle cited by organizations, at 54%, according to Flexera’s 2026 State of the Cloud Report. Migration itself is a broader category than most people assume. It’s not just “on-prem to public cloud.” It also covers moving from public cloud back to private, switching providers entirely, consolidating data centers, or relocating a VMware estate into VCF. 

Below are the ten challenges that most often derail these projects, along with what a structured, well-managed approach does to reduce each one.

1. Migrating Without a Clear Cloud Strategy

A migration can hit every deadline and still be a failure if nobody defined what success looked like going in.

That’s what happens when the destination gets picked before the workload’s actual requirements are understood. Teams end up with a technically clean move that does nothing for cost, performance, or agility. 

The fix is to set measurable goals before choosing a target: lower cost, faster deployment, better compliance, whatever it is. Then build a workload-placement framework and apply the migration “Rs”: rehost, relocate, replatform, refactor, retain, retire, and repurchase, separately for each application rather than forcing one strategy across the board. 

2. Missing Application Dependencies

Applications rarely run alone. They lean on databases, identity services, APIs, firewall rules, and scheduled jobs that often live outside the scope anyone originally wrote down. This is where projects lose the most time: According to Flexera, 54% of organizations struggled with understanding dependencies, 44% with technical feasibility, and 43% with comparing costs across environments. 

The way through is a validated inventory built from actual observed dependency and performance data, not an old configuration database that nobody’s updated in two years. That inventory becomes the backbone for sequencing migration waves in the right order.

3. Legacy Application Compatibility

Older systems carry baggage that doesn’t disappear just because the environment changes.

Unsupported operating systems, hard-coded IP addresses, physical hardware keys, and outdated middleware all follow an application through a straight lift-and-shift. The constraints just move house with it. 

Classifying each app before migration (rehost, relocate, replatform, refactor, retain, retire, repurchase) and running proofs of concept on the riskiest ones catches this early. For VMware-heavy environments, HCX enables low-disruption relocation and network extension, which supports a simple principle: Modernize at the pace the application allows, not the pace the project calendar demands.

4. Complex Data Transfers

Volume, available bandwidth, how fast the data changes, and how sensitive it is all combine to create real risks, including incomplete transfers, corrupted records, or residency violations if data ends up somewhere it legally shouldn’t. Solving this means defining classification, encryption, seeding and incremental replication, integrity checks, a clear write-freeze window, and a rollback plan before a single byte moves. 

For very large datasets, offline or staged transfer beats one long internet connection every time. There’s also a data-gravity argument for private cloud here: Sensitive, high-volume data often belongs in a controlled, managed environment rather than spread across whatever public-cloud region happened to be convenient.

5. Security Risks During Migration

The transition period is when the attack surface is widest, not the steady state before or after it.

Fifty-five percent of organizations say cloud is harder to secure than on-premises infrastructure, only 8% encrypt at least 80% of their cloud data, and 68% name stolen credentials as the fastest-growing attack tactic, per the 2025 Thales Cloud Security Study. The following rules address most of that exposure before workloads ever arrive: 

• A hardened landing zone
• Least-privilege access
• Mandatory MFA
• Credential rotation
• Centralized key management
• Deny-by-default network

A managed provider also brings something individual IT teams often can’t sustain alone: continuous patching, monitoring, and incident response that doesn’t stop the day the migration project closes.

6. Compliance and Data-Residency Requirements

Migration can quietly change where data physically sits, who can access it, who holds the encryption keys, and how audit evidence gets collected, and none of that shows up until an auditor asks. What matters are: 

• Mapping regulated data
• Defining a clear shared-responsibility matrix
• Verifying the provider’s audit history
• Preserving audit trails through the move 

No platform does that on its own. This is one area where a dedicated or managed private cloud earns its keep, since it can support HIPAA, HITRUST, PCI DSS, and SOC 2 scopes with infrastructure built for that purpose from the start.

7. Cost Overruns and Licensing Surprises

Remediation work, egress charges, running parallel environments during cutover, disaster recovery, and licensing changes all add up quietly. Cost remains the number one cloud challenge at 85%, and estimated waste has climbed to 29%, according to Flexera 2026. 

A full business case, one that rightsizes against actual utilization and puts tagging, budgets, and forecasting in place from day one, closes most of that gap. Private cloud offers something public cloud struggles with here: predictable capacity for stable workloads, and modern VCF platforms now add project-level cost reporting so spend doesn’t stay a mystery until the invoice arrives.

8. Downtime and Cutover Risk

Cutover is where all the planning either pays off or gets exposed.

The cost of getting it wrong is real: 57% of major outages cost more than $100,000, and one in five tops $1 million, according to the Uptime Institute’s 2026 Annual Outage Analysis. The following can turn cutover from a single high-stakes event into a tested, repeatable process: 

• Breaking the migration into waves
• Starting with low-risk workloads
• Defining RTO and RPO up front
• Setting go/no-go criteria
• Naming who has rollback authority

For critical applications, near-zero-downtime replication should be the default. Additionally, treat cutover as connected to backup and disaster recovery testing rather than as an isolated milestone with nothing behind it.

9. Cloud Skills Gaps and Team Silos

Migration cuts across infrastructure, security, applications, and finance all at once, and most organizations aren’t structured to make that many decisions together.

According to Broadcom, 33% of organizations cite siloed teams as their top private-cloud adoption barrier, 30% point to inadequate in-house expertise, and 80% now lean on outside professional services to fill the gap. A cross-functional team with a real RACI matrix, a shared decision log, and clearly assigned day-two ownership prevents the late-stage conflicts that stall projects.

10. Hybrid-Cloud and Day-Two Management Complexity

Leftover source systems, multiple cloud providers, and fragmented monitoring tools pile up fast. According to HashiCorp’s 2025 Cloud Complexity Report, 52% call cloud complexity a top challenge, and 42% cite poor visibility as a major barrier. What prevents that complexity from becoming permanent includes: 

• Treating post-migration optimization as its own formal phase
• Reviewing performance, cost, backup success, and configuration drift
• Decommissioning old infrastructure

It’s telling that Google’s own migration framework includes an explicit “optimize” stage after deployment. Migration doesn’t end when the workload lands. That’s simply where day-two operations begin.

Plan Your Migration Around the Right Destination

None of these ten problems is solved by moving faster or moving everything at once. The safest migration is the one that puts each workload in the environment it needs, protects the business while it gets there, and leaves behind an operating model someone can run.

At OTAVA, we help organizations work through exactly these cloud migration challenges: assessing dependencies, designing compliant private and hybrid cloud environments, migrating VMware and business-critical workloads into managed VCF, and staying on to manage the infrastructure after cutover. If you’re weighing where your workloads belong, talk to our team about a workload assessment.