Mitigating Cloud Migration Missteps

Jonathan LaCour
Mission

Though the cloud may seem ubiquitous at this point, not everyone has made the move. The many challenges with migration give some organizations pause. More than half of migration projects fail due to hidden complexities and misaligned goals. However, if you're aware of the potential setbacks going into your migration process, you can prevent those pitfalls, resulting in more successful transformation with less friction.

Though migrating to the cloud offers myriad advantages over staying on-prem, there are some potential obstacles to be aware of. With thoughtful preparation and strategic implementation, you can navigate these hurdles to execute a seamless migration that makes the most out of your cloud investment. I've outlined some of the most common challenges below, as well as strategies for overcoming them.

Failing to plan = planning to fail

It's a cliche, but it's true. To properly prepare for the transition, it's critical that you have a strong understanding of what your infrastructure will look like before and after the migration, including dependencies, performance characteristics, and required operational changes. Having a plan in place will not only minimize risk, it will enable you to handle your migration with confidence.

Curtailing costs

Without sufficient oversight, cloud migration can bust budgets. Before embarking on your migration, perform analysis, and estimate your post-migration costs. Deploy tooling to track and monitor costs and have a process to react to unexpected spikes. With the right planning, tooling, and governance, you will be able to predict, report on, and control your costs.

Ensuring security

Transitioning from an on-prem workload to the public cloud represents a significant paradigm shift. Limiting risk, preventing breaches, and enabling rapid incident response will still be your primary goals, but the tactics to achieve these goals will be different. As part of your migration planning, implement robust security processes, like data encryption, multi-factor authentication and routine security assessments, to safeguard information during the transition and into the future.

Maintaining compliance

Migrating to the cloud doesn't change regulatory requirements and legal standards. Maintain compliance by thoroughly understanding applicable regulations like GDPR or HIPAA and partnering with cloud vendors to satisfy these requirements.

Deterring downtime

Migrating production workloads inherently creates risk. Define your availability goals in advance, planning carefully for a phased transition. Understand your customer and stakeholder commitments, and ensure that you have the right process and tooling in place to ensure that you meet them.

Championing organizational adoption

Change resistance often deters adoption, but with the right plan, you can proactively prevent frustrations. To get everyone on board, involve stakeholders early on, ensure everyone has the training to succeed, and maintain transparency around the importance and benefits of migration.

Choosing and vetting vendors

Selecting the right cloud service provider is critical for preventing problems down the line. When vetting vendors, keep scalability, security, compliance, and cost top of mind. Making sure their services align with your business needs now will help facilitate future-proofed success.

Staying aware of what challenges may arise will help you proactively work toward preventing them from happening at all. With these potential setbacks, as well as strategies for solving them, in mind, you can help ensure that your migration process runs as smoothly as it can.

Cloud migration goes beyond just a technical change. It's the next step in complete digital transformation. This evolution allows your organization to nurture and encourage innovation, expand capabilities, and stay relevant in the always-accelerating business environment. With strategic migration plans in place and an awareness of common stumbling blocks to avoid, you're opening the door to enhanced operational efficiency, stronger data protections, and business development that drives long-term growth.

Jonathan LaCour is CTO of Mission

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Mitigating Cloud Migration Missteps

Jonathan LaCour
Mission

Though the cloud may seem ubiquitous at this point, not everyone has made the move. The many challenges with migration give some organizations pause. More than half of migration projects fail due to hidden complexities and misaligned goals. However, if you're aware of the potential setbacks going into your migration process, you can prevent those pitfalls, resulting in more successful transformation with less friction.

Though migrating to the cloud offers myriad advantages over staying on-prem, there are some potential obstacles to be aware of. With thoughtful preparation and strategic implementation, you can navigate these hurdles to execute a seamless migration that makes the most out of your cloud investment. I've outlined some of the most common challenges below, as well as strategies for overcoming them.

Failing to plan = planning to fail

It's a cliche, but it's true. To properly prepare for the transition, it's critical that you have a strong understanding of what your infrastructure will look like before and after the migration, including dependencies, performance characteristics, and required operational changes. Having a plan in place will not only minimize risk, it will enable you to handle your migration with confidence.

Curtailing costs

Without sufficient oversight, cloud migration can bust budgets. Before embarking on your migration, perform analysis, and estimate your post-migration costs. Deploy tooling to track and monitor costs and have a process to react to unexpected spikes. With the right planning, tooling, and governance, you will be able to predict, report on, and control your costs.

Ensuring security

Transitioning from an on-prem workload to the public cloud represents a significant paradigm shift. Limiting risk, preventing breaches, and enabling rapid incident response will still be your primary goals, but the tactics to achieve these goals will be different. As part of your migration planning, implement robust security processes, like data encryption, multi-factor authentication and routine security assessments, to safeguard information during the transition and into the future.

Maintaining compliance

Migrating to the cloud doesn't change regulatory requirements and legal standards. Maintain compliance by thoroughly understanding applicable regulations like GDPR or HIPAA and partnering with cloud vendors to satisfy these requirements.

Deterring downtime

Migrating production workloads inherently creates risk. Define your availability goals in advance, planning carefully for a phased transition. Understand your customer and stakeholder commitments, and ensure that you have the right process and tooling in place to ensure that you meet them.

Championing organizational adoption

Change resistance often deters adoption, but with the right plan, you can proactively prevent frustrations. To get everyone on board, involve stakeholders early on, ensure everyone has the training to succeed, and maintain transparency around the importance and benefits of migration.

Choosing and vetting vendors

Selecting the right cloud service provider is critical for preventing problems down the line. When vetting vendors, keep scalability, security, compliance, and cost top of mind. Making sure their services align with your business needs now will help facilitate future-proofed success.

Staying aware of what challenges may arise will help you proactively work toward preventing them from happening at all. With these potential setbacks, as well as strategies for solving them, in mind, you can help ensure that your migration process runs as smoothly as it can.

Cloud migration goes beyond just a technical change. It's the next step in complete digital transformation. This evolution allows your organization to nurture and encourage innovation, expand capabilities, and stay relevant in the always-accelerating business environment. With strategic migration plans in place and an awareness of common stumbling blocks to avoid, you're opening the door to enhanced operational efficiency, stronger data protections, and business development that drives long-term growth.

Jonathan LaCour is CTO of Mission

Related Links

Hot Topics

The Latest

Alert Fatigue Is No Longer a Morale Problem, It's a Reliability Risk and a System Failure

For years, production operations teams have treated alert fatigue as a quality-of-life problem: something that makes on-call rotations miserable but isn't considered a direct contributor to outages. That framing doesn't capture how these systems fail, and we now have data to show why. More importantly, it's now clear alert fatigue is a symptom of a deeper issue: production systems have outgrown the current operational approaches ...

Most Enterprises Think They Can Switch AI Vendors in a Month ... Most Who've Tried Couldn't

I was on a customer call last fall when an enterprise architect said something I haven't been able to shake. Her team had just spent four months trying to swap one AI vendor for another. The original plan said three weeks. "We didn't switch vendors," she told me. "We rebuilt half our integrations and discovered what we'd actually been depending on." Most enterprise leaders don't expect that to be the experience ...

Your Observability Stack Has a Telemetry Pipeline Problem

Ask any senior SRE or platform engineer what keeps them up at night, and the answer probably isn't the monitoring tool — it's the data feeding it. The proliferation of APM, observability, and AIOps platforms has created a telemetry sprawl problem that most teams manage reactively rather than architect proactively. Metrics are going to one platform. Traces routed somewhere else. Logs duplicated across multiple backends because nobody wants to be caught without them when something breaks. Every redundant stream costs money ...

Operator to Orchestrator: 80% of IT Pros See Shift in Role as AI Permeates Workflows

80% of respondents agree that the IT role is shifting from operators to orchestrators, according to the 2026 IT Trends Report: The Human Side of Autonomous IT from SolarWinds ...

Gartner: 40% of Organizations Deploying AI Will Use AI Observability to Monitor Model Performance by 2028

40% of organizations deploying AI will implement dedicated AI observability tools by 2028 to monitor model performance, bias and outputs, according to Gartner ...

Almost Half of AI-Generated Code Fails in Production

Until AI-powered engineering tools have live visibility of how code behaves at runtime, they cannot be trusted to autonomously ensure reliable systems, according to the State of AI-Powered Engineering Report 2026 report from Lightrun. The report reveals that a major volume of manual work is required when AI-generated code is deployed: 43% of AI-generated code requires manual debugging in production, even after passing QA or staging tests. Furthermore, an average of three manual redeploy cycles are required to verify a single AI-suggested code fix in production ...

AI Requires Design, Not Edicts

Many organizations describe AI as strategic, but they do not manage it strategically. When AI plans are disconnected from strategy, detached from organizational learning, and protected from serious assumptions testing, the problem is no longer technical immaturity; it is a failure of management discipline ... Executives too often tell organizations to "use AI" before they define what AI is supposed to change. The problem deepens in organizations where strategy isn't well articulated in the first place ...

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Across the enterprise technology landscape, a quiet crisis is playing out. Organizations have run hundreds, sometimes thousands, of generative AI pilots. Leadership has celebrated the proof of concept (POCs) ... Industry experience points to a sobering reality: only 5-10% of AI POCs that progress to the pilot stage successfully reach scaled production. The remaining 90% fail because the enterprise environment around them was never ready to absorb them, not the AI models ...

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Today's modern systems are not what they once were. Organizations now rely on distributed systems, event-driven workflows, hybrid and multi-cloud environments and continuous delivery pipelines. While each adds flexibility, it also introduces new, often invisible failures. Development speed is no longer the primary bottleneck of innovation. Reliability is ...

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Seeing is believing, or in this case, seeing is understanding, according to New Relic's 2025 Observability Forecast for Retail and eCommerce report. Retailers who want to provide exceptional customer experiences while improving IT operations efficiency are leaning on observability ... Here are five key takeaways from the report ...