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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

Hot Topics

The Latest

Pilots are everywhere, stakeholders are seeking results, businesses are pushing for new tools, and IT teams are being asked to make AI secure, reliable, and useful at scale. But as organizations move from testing AI to operationalizing it, many are discovering that the biggest barrier is not the model, the use case, or even the budget. It is the file data foundation within ...

Fast or cheap? For most of my career in engineering, speed and quality sat on opposite ends of a seesaw. The "OR" in "fast or cheap" was non-negotiable. It was expected that pushing for faster releases meant that something in quality would give way. Tightening quality controls meant the schedule slipped. Every engineering leader I know has lived some version of that tradeoff ... The seesaw is starting to level out ...

I have been building enterprise software for more than 20 years ... One thing stays true across all of it: You do not find out your foundation is wrong during the crisis. You find out when the debt comes due. For a lot of organizations, that bill is arriving now. New research ... puts hard numbers on something practitioners have been sensing for a while. The telemetry problem isn't coming. It's already here ...

The rapid growth of AI workloads is pushing traditional log management approaches to their limits, according to The State of Log Management 2026 report from Dynatrace. Modern logs have become critical to understanding, validating, and securing AI-driven decisions, helping organizations ensure reliability, compliance, and performance at scale. However, the volume and complexity of AI telemetry are overwhelming legacy tools ...

For years, secure connectivity has relied on a familiar pattern: route traffic back to centralized gateways, inspect it, and then allow access. This model worked when applications lived in a handful of data centers and users were largely confined to offices. That model is now under strain. Applications are distributed across clouds, users connect from everywhere, and real-time workloads demand performance that centralized inspection points struggle to deliver. As traffic volumes grow and latency expectations shrink, routing everything through a small number of control points has become both a performance bottleneck and a resilience risk. The future of secure connectivity requires a different approach ...

The AI experimentation phase is over, and the private cloud is where enterprise AI workloads are being deployed for security and scale, according to Private Cloud Outlook 2026, a new report from Broadcom ... 2026 marks an acceleration into a full AI tipping point. The shift is being shaped by three forces — costs, complexity, and control — that public cloud environments are increasingly failing to address for production AI at scale. Key findings from the report include ...

44% of organizations have reported an outage in the past year tied to suppressed or ignored alerts, and 78% had at least one incident where no alert was fired at all ... Engineers learned about failures from customers. That gap between what our tools report and what our customers experience is the problem DevOps teams have been quietly solving with GenAI tooling, even as most enterprises continue to run their NOCs on manual alert triage ...

Cloud outages are usually described as technical failures. When a service goes down, a dependency breaks, or a region has issues, the focus immediately shifts to infrastructure. But if you look closely at how these incidents actually unfold, the root cause is rarely the technology itself. It is almost always tied to decisions made earlier, during design, implementation, or day-to-day operations. The system behaves the way it was built. The real question is how it was built ...

77% of leaders say their teams need AI skills urgently. 64% say their organization plans to train current employees rather than hire new ones. So far, so reasonable. The part that surprised me is who's been put in charge: 34% of those leaders say IT and engineering own the AI skills mandate. Learning and Development or HR own it at 7% of organizations. That's roughly five-to-one in favor of the people who understand the tools, over the people whose actual job is teaching adults how to learn new ones ...

In the ever-evolving digital landscape, enterprises are increasingly focused on enhancing their observability stacks to gain deeper insights into their IT environments. Observability has become a cornerstone of modern IT operations, enabling organizations to monitor, diagnose, and optimize their systems with unprecedented precision. However, a critical piece of the puzzle often goes unnoticed in this transformation: IBM i ...

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

Hot Topics

The Latest

Pilots are everywhere, stakeholders are seeking results, businesses are pushing for new tools, and IT teams are being asked to make AI secure, reliable, and useful at scale. But as organizations move from testing AI to operationalizing it, many are discovering that the biggest barrier is not the model, the use case, or even the budget. It is the file data foundation within ...

Fast or cheap? For most of my career in engineering, speed and quality sat on opposite ends of a seesaw. The "OR" in "fast or cheap" was non-negotiable. It was expected that pushing for faster releases meant that something in quality would give way. Tightening quality controls meant the schedule slipped. Every engineering leader I know has lived some version of that tradeoff ... The seesaw is starting to level out ...

I have been building enterprise software for more than 20 years ... One thing stays true across all of it: You do not find out your foundation is wrong during the crisis. You find out when the debt comes due. For a lot of organizations, that bill is arriving now. New research ... puts hard numbers on something practitioners have been sensing for a while. The telemetry problem isn't coming. It's already here ...

The rapid growth of AI workloads is pushing traditional log management approaches to their limits, according to The State of Log Management 2026 report from Dynatrace. Modern logs have become critical to understanding, validating, and securing AI-driven decisions, helping organizations ensure reliability, compliance, and performance at scale. However, the volume and complexity of AI telemetry are overwhelming legacy tools ...

For years, secure connectivity has relied on a familiar pattern: route traffic back to centralized gateways, inspect it, and then allow access. This model worked when applications lived in a handful of data centers and users were largely confined to offices. That model is now under strain. Applications are distributed across clouds, users connect from everywhere, and real-time workloads demand performance that centralized inspection points struggle to deliver. As traffic volumes grow and latency expectations shrink, routing everything through a small number of control points has become both a performance bottleneck and a resilience risk. The future of secure connectivity requires a different approach ...

The AI experimentation phase is over, and the private cloud is where enterprise AI workloads are being deployed for security and scale, according to Private Cloud Outlook 2026, a new report from Broadcom ... 2026 marks an acceleration into a full AI tipping point. The shift is being shaped by three forces — costs, complexity, and control — that public cloud environments are increasingly failing to address for production AI at scale. Key findings from the report include ...

44% of organizations have reported an outage in the past year tied to suppressed or ignored alerts, and 78% had at least one incident where no alert was fired at all ... Engineers learned about failures from customers. That gap between what our tools report and what our customers experience is the problem DevOps teams have been quietly solving with GenAI tooling, even as most enterprises continue to run their NOCs on manual alert triage ...

Cloud outages are usually described as technical failures. When a service goes down, a dependency breaks, or a region has issues, the focus immediately shifts to infrastructure. But if you look closely at how these incidents actually unfold, the root cause is rarely the technology itself. It is almost always tied to decisions made earlier, during design, implementation, or day-to-day operations. The system behaves the way it was built. The real question is how it was built ...

77% of leaders say their teams need AI skills urgently. 64% say their organization plans to train current employees rather than hire new ones. So far, so reasonable. The part that surprised me is who's been put in charge: 34% of those leaders say IT and engineering own the AI skills mandate. Learning and Development or HR own it at 7% of organizations. That's roughly five-to-one in favor of the people who understand the tools, over the people whose actual job is teaching adults how to learn new ones ...

In the ever-evolving digital landscape, enterprises are increasingly focused on enhancing their observability stacks to gain deeper insights into their IT environments. Observability has become a cornerstone of modern IT operations, enabling organizations to monitor, diagnose, and optimize their systems with unprecedented precision. However, a critical piece of the puzzle often goes unnoticed in this transformation: IBM i ...