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Cloud Migration Delays Are Putting Businesses at Risk

How to Build a Strategy for Long-Term Success
Jonathan LaCour
Mission

Over the past 18 months, AI has been improving at a breakneck pace, and businesses globally are itching to take advantage of the most transformational new technology in decades. But, the harsh reality is that not all businesses are running on modern cloud infrastructure. Critically, their data estate requires significant evolution to even begin taking advantage of AI. They’re starting the race from the parking lot.

The explosion of generative AI and machine learning capabilities has fundamentally changed the conversation around cloud migration. It's no longer just about modernization or cost savings — it's about being able to compete in a market where AI is rapidly becoming table stakes. Companies that can't quickly spin up AI workloads, feed models with data at scale, or experiment with new capabilities are falling behind faster than ever before.

But here's what I'm seeing: many organizations want to capitalize on AI, but they're stuck. They're encumbered by legacy, and the internal friction around moving to public cloud is real. Security concerns, compliance questions, technical debt, cost control anxiety — these aren't trivial objections. They're legitimate concerns that slow everything down while the opportunity cost keeps growing.

What's Actually Holding Companies Back

The Flexera 2025 State of the Cloud Report nails the two biggest blockers: 77% of organizations cite security as a top cloud challenge, and 84% struggle with cost control. These aren't just survey numbers — they're the reasons why cloud initiatives stall in committee meetings and budget reviews.

If you're a CTO or infrastructure leader, you're being asked to move faster on AI while simultaneously being told to lock down security and control costs. That's a tough position. And when you're dealing with legacy systems that have been running business-critical workloads for years, the risk of a botched migration feels very real.

The problem is that waiting doesn't make it easier. Technical debt compounds. The gap between what your business needs and what your infrastructure can deliver just keeps widening. And critically, you're missing the window to build AI capabilities while your competitors are already experimenting and learning.

AI as the Accelerator

Here's some good news: the same AI technology creating urgency can also help solve the migration challenge. Business Insider recently covered how organizations are using AI tools to actually accelerate and de-risk migrations — mapping dependencies, estimating costs, identifying risks, and automating steps that used to require weeks of manual analysis.

This matters because it addresses both sides of the equation. You can move faster (which you need to do to unlock AI capabilities) while also reducing risk (which addresses those security and governance concerns that are keeping stakeholders up at night). AI-assisted migrations can catch configuration issues, predict cost impacts, and identify security gaps before they become problems.

But — and this is important — tools alone don't solve organizational readiness issues. You still need clear objectives, cross-functional alignment, and a realistic understanding of what you're trying to achieve. The migrations that fail usually fail because of people and process issues, not technology.

Migration Is Just Step One

The other thing I want to emphasize: getting to the cloud isn't the finish line. It's the starting line.

I see companies treat cloud migration like a project with a beginning, middle, and end. They move workloads, declare victory, and move on. Then six months later, they're shocked by their cloud bill or discovering that they're not actually more agile than before.

Cloud requires continuous optimization. You need ongoing governance, regular cost reviews, performance tuning, security monitoring, and constant alignment with best practices. The cloud providers are releasing new services and capabilities constantly. The companies that win are the ones that treat cloud as a continuous practice, not a one-time project.

This is where working with an expert partner can make a huge difference, especially if your organization is in the middle of this internal shift to public cloud. A good partner doesn't just help you migrate — they help you operationalize cloud management so you're constantly optimizing, governing, and evolving your cloud estate as your business needs change.

The Bottom Line

If your organization isn't fully committed to public cloud yet, I understand the hesitancy. But AI isn't waiting for anyone. Companies that can iterate quickly on AI capabilities are going to have a significant advantage, and that requires modern cloud infrastructure.

The question isn't whether to migrate. It's whether you have the right strategy, the right approach to risk management, and the right support to do it well. Because done wrong, cloud migration is expensive and disruptive. Done right, it's the foundation for everything you're going to need to build over the next decade.

The companies that move with discipline and a clear-eyed focus on continuous improvement will be positioned to capitalize on AI and whatever comes next. The ones that keep waiting are not reducing risk — they're accumulating it.

Jonathan LaCour is CTO of Mission

Hot Topics

The Latest

For decades, enterprise networks were designed around a simple assumption: work happened inside the office. Applications lived in centralized data centers, employees connected through internal infrastructure, and security focused on protecting the perimeter that surrounded everything ... But the way organizations operate today bears little resemblance to that environment. Cloud platforms host critical applications, employees connect from homes and airports as often as they do from offices, and partners collaborate through shared systems that exist far beyond corporate walls. In short, the corporate network no longer resembles the environment it was designed to protect ...

As an analyst who researches how IT organizations design, build, and operate their networks, I find that network data is a constant source of pain. Network teams struggle with data quality, fragmentation, authority, access, and trust. And these issues undermine everything they try to do. Here are the numbers: Only 45% of network teams are completely confident in the accuracy of their network source of truth, which documents the intent of their network ...

The 2026 Global Data Center Survey from Uptime Institute reveals an industry navigating workforce constraints, escalating outage expenses, even as rising costs remain the top concern for management teams ...

The next observability gap may not be in the code. It may be under the rack. That sounds strange until you think about how AI incidents actually feel in the middle of an investigation ... The application dashboard may be accurate. It may also be stopping at the wrong boundary. AI systems depend on software, but they also depend on a dense physical stack: racks, power paths, thermal margin, maintenance activity and, in many environments, liquid cooling. Those physical dependencies can change slowly before they look like a software incident ...

Certificate expiration is the rare outage you can see coming. Every TLS certificate carries the date it stops working, so the moment it will begin breaking connections is knowable in advance. That's what makes an expired certificate such a frustrating way to lose a service. What's changing now is how often that date comes around ...

Enterprises operate different combinations of workloads across cloud, hybrid and multicloud environments. For business-critical workloads, teams need to consider monitoring and observability early so they can detect health issues, investigate failures, and understand operational impact. Organizations place workloads on cloud platforms based on a combination of technical requirements, economics, existing dependencies, organizational standards, and business priorities. Their monitoring priorities therefore depend on what they operate and where those systems run. Those priorities will not look the same for every organization ...

Top-performing businesses prioritize data-driven decision making, enabling leaders to move from intuition and gut feel towards evidence-based judgment. But that judgment is only sound when the data underpinning decisions is accurate. With incident management, data accuracy is particularly important. Long-term revenue, customer trust, and operational stability depend on high-quality data that enables teams to quickly identify and address the root cause of major incidents. Against this backdrop, governance becomes a critical endeavor to ensure the right data drives the right action ...

In MEAN TIME TO INSIGHT Episode 26, Shamus McGillicuddy, VP of Research, Network Infrastructure and Operations, at EMA discusses network compliance ... 

Most production autonomous agents do not run in a vacuum. They run inside cloud infrastructure: virtual machines, containers, pods, managed clusters or private servers. That is where most operations teams start monitoring. Is the VM alive? Is the container running? Did the pod restart? Is memory stable? Is CPU too high? Did the health check pass? Those signals are useful. They tell you whether the shell around the agent is alive. They do not tell you whether the agent inside is actually operational ...

Enterprise IT environments have never been more observable ... Yet many organizations still grapple with outages, lengthy incident resolution cycles, and increasing complexity. Most teams do not suffer from a shortage of data. They struggle to determine what deserves attention and what action to take next ... Enterprise IT operations must move beyond monitoring and visibility. The next stage of maturity is decision operations, an approach that helps teams make faster, better-informed decisions ...

Cloud Migration Delays Are Putting Businesses at Risk

How to Build a Strategy for Long-Term Success
Jonathan LaCour
Mission

Over the past 18 months, AI has been improving at a breakneck pace, and businesses globally are itching to take advantage of the most transformational new technology in decades. But, the harsh reality is that not all businesses are running on modern cloud infrastructure. Critically, their data estate requires significant evolution to even begin taking advantage of AI. They’re starting the race from the parking lot.

The explosion of generative AI and machine learning capabilities has fundamentally changed the conversation around cloud migration. It's no longer just about modernization or cost savings — it's about being able to compete in a market where AI is rapidly becoming table stakes. Companies that can't quickly spin up AI workloads, feed models with data at scale, or experiment with new capabilities are falling behind faster than ever before.

But here's what I'm seeing: many organizations want to capitalize on AI, but they're stuck. They're encumbered by legacy, and the internal friction around moving to public cloud is real. Security concerns, compliance questions, technical debt, cost control anxiety — these aren't trivial objections. They're legitimate concerns that slow everything down while the opportunity cost keeps growing.

What's Actually Holding Companies Back

The Flexera 2025 State of the Cloud Report nails the two biggest blockers: 77% of organizations cite security as a top cloud challenge, and 84% struggle with cost control. These aren't just survey numbers — they're the reasons why cloud initiatives stall in committee meetings and budget reviews.

If you're a CTO or infrastructure leader, you're being asked to move faster on AI while simultaneously being told to lock down security and control costs. That's a tough position. And when you're dealing with legacy systems that have been running business-critical workloads for years, the risk of a botched migration feels very real.

The problem is that waiting doesn't make it easier. Technical debt compounds. The gap between what your business needs and what your infrastructure can deliver just keeps widening. And critically, you're missing the window to build AI capabilities while your competitors are already experimenting and learning.

AI as the Accelerator

Here's some good news: the same AI technology creating urgency can also help solve the migration challenge. Business Insider recently covered how organizations are using AI tools to actually accelerate and de-risk migrations — mapping dependencies, estimating costs, identifying risks, and automating steps that used to require weeks of manual analysis.

This matters because it addresses both sides of the equation. You can move faster (which you need to do to unlock AI capabilities) while also reducing risk (which addresses those security and governance concerns that are keeping stakeholders up at night). AI-assisted migrations can catch configuration issues, predict cost impacts, and identify security gaps before they become problems.

But — and this is important — tools alone don't solve organizational readiness issues. You still need clear objectives, cross-functional alignment, and a realistic understanding of what you're trying to achieve. The migrations that fail usually fail because of people and process issues, not technology.

Migration Is Just Step One

The other thing I want to emphasize: getting to the cloud isn't the finish line. It's the starting line.

I see companies treat cloud migration like a project with a beginning, middle, and end. They move workloads, declare victory, and move on. Then six months later, they're shocked by their cloud bill or discovering that they're not actually more agile than before.

Cloud requires continuous optimization. You need ongoing governance, regular cost reviews, performance tuning, security monitoring, and constant alignment with best practices. The cloud providers are releasing new services and capabilities constantly. The companies that win are the ones that treat cloud as a continuous practice, not a one-time project.

This is where working with an expert partner can make a huge difference, especially if your organization is in the middle of this internal shift to public cloud. A good partner doesn't just help you migrate — they help you operationalize cloud management so you're constantly optimizing, governing, and evolving your cloud estate as your business needs change.

The Bottom Line

If your organization isn't fully committed to public cloud yet, I understand the hesitancy. But AI isn't waiting for anyone. Companies that can iterate quickly on AI capabilities are going to have a significant advantage, and that requires modern cloud infrastructure.

The question isn't whether to migrate. It's whether you have the right strategy, the right approach to risk management, and the right support to do it well. Because done wrong, cloud migration is expensive and disruptive. Done right, it's the foundation for everything you're going to need to build over the next decade.

The companies that move with discipline and a clear-eyed focus on continuous improvement will be positioned to capitalize on AI and whatever comes next. The ones that keep waiting are not reducing risk — they're accumulating it.

Jonathan LaCour is CTO of Mission

Hot Topics

The Latest

For decades, enterprise networks were designed around a simple assumption: work happened inside the office. Applications lived in centralized data centers, employees connected through internal infrastructure, and security focused on protecting the perimeter that surrounded everything ... But the way organizations operate today bears little resemblance to that environment. Cloud platforms host critical applications, employees connect from homes and airports as often as they do from offices, and partners collaborate through shared systems that exist far beyond corporate walls. In short, the corporate network no longer resembles the environment it was designed to protect ...

As an analyst who researches how IT organizations design, build, and operate their networks, I find that network data is a constant source of pain. Network teams struggle with data quality, fragmentation, authority, access, and trust. And these issues undermine everything they try to do. Here are the numbers: Only 45% of network teams are completely confident in the accuracy of their network source of truth, which documents the intent of their network ...

The 2026 Global Data Center Survey from Uptime Institute reveals an industry navigating workforce constraints, escalating outage expenses, even as rising costs remain the top concern for management teams ...

The next observability gap may not be in the code. It may be under the rack. That sounds strange until you think about how AI incidents actually feel in the middle of an investigation ... The application dashboard may be accurate. It may also be stopping at the wrong boundary. AI systems depend on software, but they also depend on a dense physical stack: racks, power paths, thermal margin, maintenance activity and, in many environments, liquid cooling. Those physical dependencies can change slowly before they look like a software incident ...

Certificate expiration is the rare outage you can see coming. Every TLS certificate carries the date it stops working, so the moment it will begin breaking connections is knowable in advance. That's what makes an expired certificate such a frustrating way to lose a service. What's changing now is how often that date comes around ...

Enterprises operate different combinations of workloads across cloud, hybrid and multicloud environments. For business-critical workloads, teams need to consider monitoring and observability early so they can detect health issues, investigate failures, and understand operational impact. Organizations place workloads on cloud platforms based on a combination of technical requirements, economics, existing dependencies, organizational standards, and business priorities. Their monitoring priorities therefore depend on what they operate and where those systems run. Those priorities will not look the same for every organization ...

Top-performing businesses prioritize data-driven decision making, enabling leaders to move from intuition and gut feel towards evidence-based judgment. But that judgment is only sound when the data underpinning decisions is accurate. With incident management, data accuracy is particularly important. Long-term revenue, customer trust, and operational stability depend on high-quality data that enables teams to quickly identify and address the root cause of major incidents. Against this backdrop, governance becomes a critical endeavor to ensure the right data drives the right action ...

In MEAN TIME TO INSIGHT Episode 26, Shamus McGillicuddy, VP of Research, Network Infrastructure and Operations, at EMA discusses network compliance ... 

Most production autonomous agents do not run in a vacuum. They run inside cloud infrastructure: virtual machines, containers, pods, managed clusters or private servers. That is where most operations teams start monitoring. Is the VM alive? Is the container running? Did the pod restart? Is memory stable? Is CPU too high? Did the health check pass? Those signals are useful. They tell you whether the shell around the agent is alive. They do not tell you whether the agent inside is actually operational ...

Enterprise IT environments have never been more observable ... Yet many organizations still grapple with outages, lengthy incident resolution cycles, and increasing complexity. Most teams do not suffer from a shortage of data. They struggle to determine what deserves attention and what action to take next ... Enterprise IT operations must move beyond monitoring and visibility. The next stage of maturity is decision operations, an approach that helps teams make faster, better-informed decisions ...