Cloud Migration: Why "Move First, Fix Later" Still Fails (And How to Do It Right)

I came across a post recently that told the story of a company that spent €100k moving to the cloud… and another €100k moving back on-prem. Eighteen months later, key workloads were right where they started. The punchline was simple: The cloud didn't fail them — their assumptions did.

The original post made a few good points:

• Moving a tightly coupled system to the cloud doesn't magically make it modern.
• If something is hard to maintain on-prem, it won't become easier because it now runs in another data center.
• Poor architecture becomes more expensive, not more scalable.

All of that is true. But there's one part I don't fully agree with. The problem isn't lift-and-shift itself. The problem is lifting and shifting blindly.

A lift-and-shift migration can succeed — and often should be the first step — when you go in with eyes open, backed by a proper assessment, a clear roadmap, and realistic expectations of what you're getting into. Without that, yes, you're relocating your technical debt with a bigger invoice attached.

This is where companies get hurt.

Lift-and-Shift Isn't the Enemy — Lack of Planning Is

There's a misconception that you must modernize before migrating. In reality, many organizations don't have the luxury to delay:

• Hardware is at end-of-life
• Contract renewals are forcing decisions
• Teams are stretched thin
• Security requirements keep growing

A well-executed lift-and-shift can give you breathing room. It can give you stability and predictable performance. It can buy time for the modernization work that should follow.

But only if you know what you're lifting… and why.

None of these are cloud problems. They're planning problems.

A Clear Roadmap Changes Everything

Successful cloud migrations follow a pattern. It's not magic. It's discipline.

Here's a simple, practical roadmap that works in real life — not just in diagrams:

1. Start with an Honest Assessment

Not a 150-page PDF nobody will read. A real inventory with real constraints:

• What are you actually running?
• What breaks if you move it?
• What depends on what?
• What does it cost today — and what will it cost tomorrow?

This is where your migration succeeds or fails.

2. Decide What Needs to Change Now vs. Later

Not everything must be modernized on day one. In fact, trying to do that is one of the fastest ways to stall a migration.

Ask simple questions:

• Can this app move "as is"?
• Should it be improved before we move it?
• Or should it wait because modernizing it gives better ROI?

Priorities, not perfection.

3. Create an Architecture That Can Evolve

The cloud rewards flexibility. You don't need a microservices revolution on day one, but you do need:

• A solid landing zone
• Clear networking boundaries
• Identity and access handled properly
• Logging and monitoring that actually work
• A cost model you understand

This is your foundation. It lets you migrate safely without locking yourself into old patterns.

4. Migrate in Controlled Waves

Small, predictable steps beat big, heroic migrations.

• Move what is low-risk first.
• Observe, learn, adapt.
• Fix the gaps before the next wave.

This approach builds confidence, surfaces issues early, and gives your team time to develop cloud-native skills.

5. Modernize Intentionally, Not Reactively

Once workloads are stable in the cloud, that's when the real value shows up:

• Breaking apart bottlenecks
• Automating deployments
• Building resilience instead of firefighting
• Reducing costs through right-sizing and FinOps
• Gradually removing old technical debt

Modernization becomes a roadmap, not an emergency.

Cloud Migration Is Not About Moving Servers — It's About Moving Thinking

The common thread in every failed migration is simple:

They moved too quickly, with too many assumptions, and too little understanding of what needed to change.

Good planning doesn't slow you down. It saves you from paying twice.

This is exactly why assessment and roadmap work exists. Not to complicate things, but to prevent expensive surprises later.

And yes — this is the part where consultants like me come in. Not as "cloud evangelists," but as people who've seen migrations succeed, fail, and everything in between. The job is to help organizations move for the right reasons, at the right time, with the right expectations… and to avoid writing a €200k story no one wants to share on LinkedIn.

Closing Thoughts

Cloud isn't a destination. It's a capability.

• A lift-and-shift can be a smart first move.
• A full modernization can be the long-term goal.
• A migration can be both fast and sustainable.

But only when you plan it properly.

If your organization is considering a move — or recovering from one — take the time to ask the right questions before touching the first VM. The cloud doesn't fix broken architectures. It amplifies them.

With the right roadmap, though, it can amplify everything that already works well… and open the door to what comes next.