IT Tips & Tricks

Updated 23 January 2024

Cloud Data Migration Challenges: An Overview of Three Key Barriers

What would G.I. Joe do?


Cloud migration problems?

We feel your pain, and you’re not alone. Tech research giant, Gartner, states that 83% of all data migration projects fail and that more than 50% of migrations exceed their budget. Nobody in their right mind wants to be the one responsible for either of those percentages or the side-servings of fuming bosses, downtime, irate end-users, or missing data that frequently accompany a botched migration — Cloud or otherwise.

When considering Cloud migration, Gartner’s forecast for 2024 says it all:
“Worldwide end-user spending on public cloud services is forecast to grow 20.4% to total $678.8 billion in 2024, up from $563.6 billion in 2023.”

“Cloud has become essentially indispensable,” says Sid Nag, Vice President Analyst at Gartner.

In their June 2022 report, Gartner identified three key problems that Infrastructure & Operations (I&O) leaders must overcome in order to ensure a successful Cloud migration. These three problems are still completely valid today and, per G.I. Joe, “Knowing is half the battle.” If it’s good enough for Joe, it’s good enough for us, so let’s dive into this overview of cloud migration.

Knowing is half the battle.”

— G.I. Joe


VP Research at Gartner, Phillip Dawson.

According to Gartner, cloud migration offers unique challenges. Gartner’s Philip Dawson explains, “Cloud migration initiatives for enterprise applications are often thwarted by application size, high levels of customization and insufficient skills. Before migrating applications, I&O leaders must break down the barriers by modernizing infrastructure and applications into Cloudlike configurations.”

The three identified barriers are:

  1. Application size,
  2. High levels of customization and
  3. Insufficient skills.

We’ll expand upon each of these points below.

Application Size

While virtual machines (VMs) advancements allow I&O leaders to migrate mid-sized applications (from 2TB to 6TB) to the Cloud, applications larger than 6TB cannot yet be migrated on a single VM. (The key word there is “yet.” Things change fast in the tech world.)


Gartner says that 83% of data migrations fail. Yours doesn’t have to.

Unlike new applications, the bulk of the enterprise application portfolio — about 85% of existing core IT applications — predates the Cloud and was therefore not designed using the principles of Cloud-native architecture. Examples include legacy mainframe and mid-range applications, ERP (enterprise resource planning) applications, and proprietary UNIX-based applications. These applications are often highly customized and large in size, making them incompatible with most Cloud platforms. A lift-and-shift approach for migrating legacy applications to the Cloud is seldom an effective strategy, and the approach to customized apps is discussed below.

The Impact of Customization

I&O leaders are tasked with managing a broad array of customized applications that are not designed to run in the Cloud (or even on Cloud-like on-premises infrastructure). Having identified which applications are suitable for Cloud migration, I&O leaders face another challenge: Many of their existing applications are customized and are not designed to run in the Cloud. This means that IT departments must standardize these applications before the migration can begin.

It logically follows that the path to standardization depends on the level of customization. Most legacy applications have three types of customizations:

  1. Added or customized screens and reports,
  2. Added fields or indexes/totals,
  3. Added processes and custom scripts.

The greater the level of customization, the more difficult and time-consuming it is for I&O leaders to migrate and modernize the application to the Cloud. Therefore it makes sense to kick off a migration with high-value apps that have fewer customizations, as these applications require less time and effort to standardize. The goal is to transform a lightly customized application into a configured application that has:

  • Edited text fields within configuration,
  • Hidden fields or indexes/totals,
  • Standard processes and custom scripts.

Once these issues are addressed, I&O leaders should then be able to migrate the configured application to the Cloud.

“Before migrating applications, I&O leaders must break down the barriers by modernizing infrastructure and applications into Cloudlike configurations.” — Philip Dawson, Gartner

Key Skills: Transitional and Transformational

Cloud providers often focus on providing operational and implementation skills, rather than transitional and transformational skills. In other words, the service level agreement (SLA) from the provider includes “build” and “run” (the vehicle), but not “plan” (the journey). Transitional and transformational skills are often beyond the scope of the contract, but there’s literally no point in creating a vehicle that’ll never travel the journey.


Things don't always go according to plan. But there's a reliable way to make sure that your linked data is always exactly where you want it to be.

To facilitate a smooth migration journey to the Cloud, I&O leaders need to avail themselves of four distinct skill sets:

  • Operational skills. This requires the ability to run standardized applications in the Cloud more cost-effectively than on-premises infrastructure. Cloud IaaS (infrastructure as a service) providers excel at providing infrastructure skills, and a provider’s subscription-based model is often cheaper than on-premises, project-based alternatives (at least for the first couple of years of the contract, but this will vary, provider to provider).
  • Implementation skills. This is the ability to directly move those standardized applications to the Cloud. Most Cloud providers offer this capability for configured applications. However, highly customized and complex applications could potentially be more expensive when moved to the Cloud (especially in the longer term). This means that standardization could pay for itself over time.
  • Transitional skills. This translates to the ability to move a customized app from on-premises to PaaS (platform as a service). Without specialized skills related to the systems, these transitions can be difficult, if not seemingly impossible. Cloud providers typically lack these skills and partner with a system integrator (SI) to provide this capability — at a cost — to you.
  • Transformational skills. The ability to move a customized app from on-premises to a new packaged application or SaaS (software as a service). To complete this migration, the application must be standardized, modernized and configured, which requires specialized skills that come at a premium and are generally only available from system integrators and third parties.

While Cloud IaaS providers deliver the underlying infrastructure and shine at offering operational and implementation skills in SLAs, they often rely on external partners for specialized transitional and transformational skills — resulting in an I&O skills gap.

The bulk of the enterprise application portfolio was not designed using the principles of Cloud-native architecture.

The bottom line? You may find it more cost-effective to temporarily contract your own specialist rather than paying your Cloud provider’s fees for this service. Let’s face it. There are always data migration issues, and, more specifically, Cloud data migration challenges. But that’s precisely what your specialist is there to handle for you, making them a worthwhile investment.

Suggested Solutions

Whether you’re the I&O leader or the IT professional responsible for the success of the migration, what exactly, are you supposed to do about the above points? Gartner suggests the following:

  • Classifying applications based on size helps determine the best migration path for each existing application (such as Cloud versus hosting).
  • Collaborate with application teams to standardize legacy applications by reconfiguring heavily customized applications (for hosting) and re-platforming customized applications (for Cloud).
  • Encourage modernization by complementing traditional I&O teams with transitional and transformational skills from strategic partners or system integrators (SIs).

Why Cloud Migrations Fail

Ask a gathering of IT staffers why Cloud migrations fail, and you’ll get more answers than grains of rice in a carton of Chinese takeout.

“Blame it on lack of planning,” some will say, or “selecting the wrong migration approach.” “Not testing thoroughly” is another common response. “Legacy applications” take a lot of heat, as does “talent scarcity.” Of course, “security issues” feature strongly, alongside “control and governance.” “Inadequate strategy” frequently gets the blame, along with “underestimation of complexity” and “employee resistance to change,” while some maintain that all Cloud migration failures stem from one major cause: “Lack of insight into data.”

Either way, it’s easy to see why the project failure statistics from Gartner are as high as they are. In case you don’t remember, the figures we mentioned in the first paragraph were 83% for failed data migration projects and over 50% for migrations that exceeded their budget.

Data migrations can be as individual as a fingerprint, so there’s no one-size-fits-all strategy to prevent failure — although overcoming a “lack of insight into data” is a good place to start.

The article, 5 Common (and Dangerous) Data Migration Mistakes, offers insights into how to avoid some typically overlooked migration pitfalls. Another article, Four Things Before Starting Your Data Migration states, “Failed data migration projects (heck, most failed IT projects of any kind) fail due to lack of imagination.” It’s a worthwhile read with some surprising insights.

The Fourth Wall


Don't let broken links cause disruption or bury you in service tickets.

We’ve taken a look at three potential barriers to a smooth Cloud migration, but if we’re talking broad approaches to migrating into the Cloud, there’s another issue that warrants mention: the fourth wall, as it were.

We’re willing to support your determination, leading up to your migration, to avoid black cats and refrain from walking under ladders. But if you feel like what you need is something that really makes a difference, then here’s a tip that definitely makes a difference and requires no avoidance of cats or ladders.

You’re probably aware that missing data is a frequent side-effect of data migration, and you may also know that a common cause of that missing data is the file links that break during the migration process. Missing data results in a host of things we’d all prefer to avoid, such as downtime, moaning end-users, a storm of open service tickets, grumpy bosses and you being stuck at the office long after others have left.

Want to avoid all of that? Then the smartest thing to do is to avoid the broken links phenomenon in the first place. How? With LinkTek’s LinkFixer Advanced software.

LinkFixer Advanced can be used prior to a migration to prepare your file links. After you’ve completed your migration, LinkFixer Advanced will repair any prepared links that broke, thus preventing the usual data loss.

If you’ve already completed a migration and have missing data due to broken file links, think of LinkFixer Advanced as your disaster recovery tool. It can repair broken links after the fact and instantly restore your missing data.

For more information, visit or call 727-442-1822 to speak to a friendly Service Consultant. Don’t forget to ask about the third way LinkFixer Advanced can help you.

We wish you a successful migration — whether to the Cloud or elsewhere — and a scarcity of black cats and ladders.

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