Case Study: Responding to Infrastructure Risks in a Cloud Migration

Planning for Failure to Ensure Success

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This edition of The PM Playbook reveals how a mid-sized company managed infrastructure risks during a full cloud migration. The project required tight timelines, active user environments, and critical data protection—all while maintaining downtime to a minimum.

By building a layered risk strategy from the outset, this team avoided costly surprises and delivered a successful migration with minimal disruption. You’ll learn how clear ownership, testing plans, and scenario planning can reduce uncertainty and increase team confidence.

Let’s dive in...

Introduction

A mid-sized logistics company faced a critical decision: migrate its aging on-prem infrastructure to the cloud or continue operating at increasing risk. The existing systems were stable but outdated, with limited support, patching delays, and no disaster recovery plan. Customer demand had grown, operations had scaled, but IT had fallen behind. Leadership pushed for a 90-day migration to modernize the stack and reduce costs. But the project manager saw the real challenge wasn’t the migration—it was the risk of disruption.

The company’s daily operations depended on multiple interconnected systems. Shipping data, inventory records, invoicing, and customer communications all ran through a fragile infrastructure. A single outage could halt deliveries and trigger missed SLAs. Every application had dependencies, and many of them weren’t well-documented. Migrating without a risk strategy was like trying to rewire a plane mid-flight.

The project required more than technical planning. It needed a full risk management strategy baked into the foundation. That included stakeholder alignment, cross-team testing, and fallback plans for every scenario. From the start, the team treated risk not as a task, but as a thread running through every workstream. They knew clarity and preparation would beat speed every time.

This case study shows how that mindset paid off. The team built a living risk register, ran simulations, and created rollback paths for each step. Vendors were brought into the planning, not just the delivery. By focusing on resilience, not just completion, the team protected operations and built trust. This wasn’t just a successful migration—it was a controlled, confident one.

Background

The company had grown rapidly over the last five years, expanding its customer base and distribution reach. But its infrastructure hadn’t kept up. Servers were outdated, patching was inconsistent, and failover strategies were limited. The decision to move core systems to a cloud platform was driven by cost, security, and scale, but the shift came with major risks, including data loss, integration failure, and downtime during business hours.

With daily shipments, live inventory updates, and 24/7 customer portals, any interruption could impact revenue and customer trust. The project sponsor emphasized that “failure wasn’t an option”—but the PM knew success meant planning as if it was.

Challenges

• Legacy System Dependencies: Core applications were tightly coupled with on-premises infrastructure, making it difficult to untangle dependencies.
• Downtime Sensitivity: Even brief outages could delay shipments and trigger support escalations.
• Limited Internal Expertise: The company’s IT team had never led a full-scale cloud migration.
• Vendor Coordination: The project involved multiple external vendors for cloud hosting, application support, and security.
• Data Integrity Risks: The volume and sensitivity of transactional data require careful transfer, verification, and rollback options.

Solutions Implemented

• Comprehensive Risk Register: The team identified over 40 potential infrastructure risks, grouped by severity and likelihood. Each was assigned a mitigation strategy and an owner.
• Rollback and Recovery Planning: For every migration task, the team documented a rollback procedure. They created full backups and validated them before initiating transfers.
• Red Team Testing: A “Red Team” of internal IT staff and external consultants simulated worst-case scenarios before go-live. These included server failures, corrupted files, and API disconnects.
• Vendor Alignment Meetings: Weekly triage calls with vendors ensured shared awareness of risks, dependencies, and decision points.
• Staged Migration with Pilot Users: Instead of a big bang cutover, the team migrated systems in phases, starting with a low-impact department to test performance and controls.

Results

• Zero Critical Downtime: The phased rollout and recovery plans kept core systems available throughout the transition.
• Data Integrity Maintained: 100% of critical data was verified post-migration with no rollback events required.
• Cross-Team Confidence: Using structured risk discussions improved collaboration and reduced friction during escalations.
• Improved Vendor Coordination: Vendor teams cited the PMO’s approach as the best-prepared project team they had worked with that year.
• Faster Issue Resolution: Because risks were identified early, mitigation responses were executed in under 2 hours on average during the migration window.

Key Takeaways

• Plan for Failure, Not Perfection: Building in rollback strategies and testing worst-case scenarios gives teams the confidence and options they need under pressure.
• Create a Living Risk Register: Keep your risk log active, up to date, and shared with vendors and internal stakeholders.
• Mitigation Starts with Ownership: Assign clear owners for every high-priority risk to ensure action, not just awareness.
• Stage the Cutover: A phased approach to migration lowers impact and gives teams space to validate and adjust.
• Test More Than Functionality: Simulate outages, errors, and failures, not just feature sets, to uncover hidden gaps.

Conclusion

Infrastructure risk is one of the most overlooked parts of cloud migration. Teams focus on tool selection, speed, and integration, but often forget about what happens when things go wrong. In this project, the PM didn’t let optimism cloud the reality of risk. The goal wasn’t a perfect rollout. The goal was a prepared one.

The company succeeded because it planned for what could go wrong. Red Team testing, phased deployments, and assigned contingency roles made the difference. Risks didn’t turn into delays because every scenario already had an owner and a plan in place. The team didn't improvise under pressure—they executed. That clarity saved hours—and protected operations.

Leadership played a key role by giving space to slow down and assess risk. That support built a culture where flagging issues wasn’t punished—it was expected. Monthly risk reviews continued after the migration. Preparedness became part of how the team operated. And the value extended well beyond IT.

This case proves that smart risk management isn’t about being risk-averse. It’s about being risk-ready. The best teams don’t wait to be surprised—they simulate the worst, then build systems that survive it. Risk planning isn’t extra work. It’s the difference between chaos and control. And it’s how this project finished on time, fully operational, and with zero major incidents.

Discussion Questions

• What’s the right balance between risk planning and delivery speed in a migration?
• How can project managers encourage honest risk reporting without causing fear?
• What role should vendors play in your risk register and mitigation plans?
• How do you simulate failure without disrupting current operations?
• What tools are most effective for documenting and monitoring infrastructure risk?

Further Analysis

• Compare risk planning strategies for phased vs. big-bang migrations.
• Analyze the long-term operational impact of structured rollback procedures.
• Investigate how Red Team testing can improve project outcomes beyond security.
• Explore best practices for involving non-technical stakeholders in infrastructure risk conversations.
• Evaluate the role of project sponsors in creating psychological safety for risk discussions.

Areas for Future Research

• Examine the effectiveness of AI-driven risk prediction tools in infrastructure projects.
• Explore how hybrid cloud models affect traditional infrastructure risk categories.
• Investigate the relationship between project size and breakdowns in risk communication.
• Study post-mortem processes and how they influence future risk planning maturity.
• Analyze the scalability of risk registers across enterprise Project Management Offices (PMOs).

Follow me for more Project Management Insights: LinkedIn | Substack Newsletter

🎙️ Love real stories like this one? Check out our new podcast “2 Disgruntled PMs” on Spotify and Amazon to catch full episodes, behind-the-scenes breakdowns, and real-world strategies you won’t find in the textbooks.

Follow the 2 Disgruntled PMs Podcast LinkedIn page for episode drops, news, and updates.

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