9 Cloud Migration Challenges and Solutions For CTOs in 2023

Worried about cloud migration challenges? Here are some practical solutions for your cloud migration success!

August 10, 2021
7 mins read
Last Updated February 01, 2023
Cloud migration challenges

9 Cloud Migration Challenges and Solutions For CTOs in 2023

How do you reduce the time-to-market when your engineers have to deal with thousands of microservices? That was the question Pinterest was looking for an answer for, while they’re figuring out a way to execute the rapid deployment of their products. Ultimately, they decided to use a hybrid-cloud approach by migrating some applications to cloud services and keeping the core data at their local infrastructure. 

However, it was not the decision to migrate but the execution of the migration process which posed a massive challenge for Pinterest. The most significant challenge was to modernize their legacy applications which were not compatible with cloud-based services. Another challenge was to keep the cost of operations optimal with reliable automation. 

The Pinterest team used a re-platform strategy to migrate some applications directly and tweaked others to be compatible with cloud services. Modernization of applications was achieved by leveraging containers. The result was a 30% reduction in cost per instance and on-demand scaling with reliable failover policies. While it may seem smooth sailing for Pinterest, it is not the same for others.

Cloud migration Statistics

In 2020, the spending on cloud services by organizations worldwide was close to $125 billion and will rise to $160 billion by the end of 2021. As the global spending on cloud computing is increasing, organizations face migration challenges despite heavy expenses. Though there is no way to skip past the challenges you may face during cloud migration, here are some solutions that you can use for your business.

Simform provides leading cloud migration consulting services that have helped organizations successfully move to the cloud and overcome migration challenges efficiently with the right strategies. Contact us today to avail our expert cloud services!

Top 9 Cloud Migration Challenges and Solutions

#1. Compatibility Challenge

One of the easiest ways to migrate your apps and data is to just “lift and shift” them in a cloud environment. However, shifting your data and apps from one environment to another is not that easy in real-life scenarios. Take an example of DigitalNZ, which is an advanced search-based website for digital content supported by the National Library of New Zealand. 

There were two significant challenges for DigitalNZ- knowledge, and compatibility. The first challenge was a lack of knowledge on cloud-based technologies, and the second was legacy applications that were incompatible with a cloud environment. DigitalNZ used on-premise infrastructure with different runtime environments, operating systems, and security measures than cloud environments. 

So, how did they resolve the challenges of compatibility?


DigitalNZ used a phased approach to their cloud migration process, which included three phases,

Phase1- Shifting apps that do not need any changes for compatibility

Phase2- Aligning their virtual network to interact with on-premise infrastructure

Phase3- Re-architectured some applications while decommissioning the obsolete ones.

Taking the cue from DigitalNZ, organizations can either re-architecture their existing apps to make them compatible with the cloud environments or retire them. The decision depends on the type of application and its impact on the business capabilities.

#2. Avoiding Vendor Lock-in

Migrating to the cloud can be great for your business, but sometimes it results in restrictions, often referred to as vendor lock-in. When organizations choose a cloud vendor, they analyze their existing requirements. As they scale, higher interoperability is needed, which is not always feasible with every cloud-based service, affecting your operations. 

Negative impacts of the vendor lock-in are,

  • Getting stuck to an inefficient cloud-based service that does not deliver as per requirements
  • Changes in the services that no longer are feasible with your current business requirements.
  • The massive price increase by the current vendor may put a load on your existing IT budget. 
Types of cloud

Solution- For CTO’s, vendor lock-in can be a real problem, and the best solution is choosing to go hybrid instead of relying on a single vendor. With a multi-cloud approach, you can keep the sensitive data on a VPC or Virtual Private Cloud infrastructure and non-sensitive services on the public cloud. It is the new normal in cloud migrations, and as per an IDC report in March 2020, more than 90% of enterprises will rely on the hybrid cloud by the end of 2022. 

Expert Qoutes

#3. Choosing Cloud Services

There are many cloud service providers with different services. Moreover, not every service is in sync with your business requirements. So, rather than spending on a suite of services, organizations should choose specific cloud-based services. However, the challenge lies in identifying the exemplary cloud service for your business.

For example, Abode systems offer DIY home security solutions that are simple to set up for homeowners. Camera sensors play a pivotal role in Abode’s solutions which enables consumers to monitor their homes remotely. 

These sensors were powered by a third-party commercial media streaming technology which created multiple challenges. So, Abode chose Amazon Kinesis Video Streams, a fully managed service that allows secure video streaming from connected devices to AWS for playback, analytics, and other processing. 

Solution-  Consult with cloud service providers and let them assess your existing systems, and then understand where these services stand in terms of application. It will help you decide better whether or not the service is suitable for your project or not.

#4. Not Configuring Right Strategy

Cloud migration strategies are roadmaps to the entire process of shifting your assets to the cloud infrastructure. Most of the CTOs face the challenge of choosing an optimal strategy that fits their business requirements. If the strategy is wrong, there will be less ROI and lower uptime resulting in inefficient business operations. 

For example, the “lift and shift” approach is a simple approach to moving your assets directly to the cloud, but it is not a one-size-fits-all cloud migration strategy. Especially if your applications have compatibility issues, you may want to tweak it a little. Similarly, if the application runtime environment is different from the cloud environment, you can’t just “lift and shift.”

Solution- The best way to decide on a suitable strategy is to analyze your business requirements, assess different use cases, and create a cloud migration plan. To make such a plan, you will need to have a sound pre-migration assessment, which can help you audit existing systems’ data and analyze the need for scalability, obsolete components, and compatibility.

Cloud migration stats

Cloud migration strategies also depend on specific business requirements. For example, a survey was conducted with CTOs of four business verticals- Banking, Fintechs, Insurance, and Telecoms on cloud adoption strategies. While Fintechs relied more on cloud-native development, the Telecom industry primarily used the lift and shift approach.

Expert Quotes

Learn More About Different Cloud MIgration Strategies

#5. Maintaining Data Security & Risk Assessment

Every organization has sensitive data, and identifying them is critical. Assessment of essential data and core services will help you understand the need for secure cloud migration practices. Unfortunately, most risk assessment programs lack a framework that can help them create a reliable management plan. 

Every risk management framework needs the identification of risks and security policies to counter them. According to Harvard Business Review, there are three categories of risks that every organization faces. These are preventable risks, strategic risks, and external risks. 

For cloud migration, data leaks and data loss can be a preventable risks to some extent. But, you will need a centralized security policy. One can enforce compliance and apply an infrastructure-wide secure access process which helps in reducing the loss of sensitive data. However, creating a centralized policy is not that easy and needs an understanding of all the risk types, critical access checkpoints, and authentication methods.

Solution- Opting for SaaS (Security as a Service) can help you reduce such security risks. In addition, many cloud providers offer pre-built security features to help their customers with data security. Still, you can go beyond such features and collaborate with cloud vendors to develop Security as a Service.

#6. Prioritization Problems

Prioritization is one of the most important aspects of cloud migration. It is a process of identifying critical services and components that you need to migrate first or prioritize to ensure zero downtime. 

Most CTOs have a hard time aligning their datasets with the technical drivers. However, such alignment can enable organizations to collect data elements and create a ranking for each application to prioritize if done right. 

Solution- To better align the technical drivers and data elements obtained through pre-migration assessment, you need pre-defined business metrics. Then, define these metrics and the priority of workload migration after a brainstorming session with all the stakeholders. For example, if your primary tech driver is agility, you may consider the number of deployments or iterations an application will have in a year.

Expert quotes

At the same time, if the primary driver is cost reduction, you may need to target the annual savings and aspects of cloud migration that can affect. Resiliency can be defined in terms of lost revenues per hour of downtime for better prioritization. 

Checkout The Most Comprehensive Cloud MIgration Checklist

#7. Skill Shortage

Cloud migration will require skill up-gradation for the existing employees, especially for an organization using a legacy architecture. Lack of skill is a massive cloud migration challenge, and many organizations spend enormous money on training. 


A study from Forrester suggests that cloud monitoring skills are one with the highest shortage in internal staff for organizations with a gap of around 12%. At the same time, cloud ecosystem expertise amounts to a skill shortage of 11%. 

Simultaneously, the cost expertise has a shortfall of 11%, with an application architecture skill gap of 8%. Apart from the training, some skillsets may take more time to master that may eventually increase the migration costs. For some skill sets, training is not enough, and enterprises need a more reliable solution. 

Solution- The best way to bridge the skill gap is to partner with a cloud management partner to help through extended teams. For example, at Simform, we have helped many organizations with different cloud management, deployment projects. One such example is Mission Rabbies. We assisted the non-profit organization in migrating from Azure to AWS cloud with a skilled engineering team to ensure high availability and zero downtime. 

#8. Cloud Migration Costs

Cloud migration costs are among the biggest challenges that CTO’s encounter due to lack of skills, compatibility issues, higher cost of data migrations, wrong migration strategy, lack of data recovery provisions, etc. 

Enterprises spend a lot of capital on tweaking their existing infrastructure to be compatible with the cloud environment. Another cloud migration challenge that is related to overall costs is the transfer of massive data and recovery. 

Organizations lose data during migrations due to a lack of DR (Data Recovery) provisions and then recover it through third-party tools. Therefore, the cost of third-party tools is an extra cost that can be avoided through provisions for DR. 

Cloud migration strategies are also a significant contributor to the costing issues; if not in sync with your business requirements. Even when you don’t prioritize your migration workloads, there can be disruptions resulting in revenue loss.  

Solution- Cloud migration costs depend on the scalability of your projects and specific needs. Every cloud-managed service has a different pricing structure, and you will need a pre-migration assessment to configure the cost. 


For example, Amazon EC2 charges based on instances that are terminated once the functionality is over. So, you only pay for what you use. However, how many instances you need is what you can configure through the assessment of your systems.

#9. Migrating Massive Database

Imagine processing more than 100 petabytes of data with 20000 daily data pipeline runs? That is what Spotify was dealing with while having its infrastructure on-premise. Expanding teams across four different geographical regions to manage such a massive database was difficult, so they decided on cloud migration to GCP(Google Cloud Platform). 

Most organizations choose cloud migration to solve the data storage issue and the need for scalability, flexibility, and others. However, they faced a problem while deciding whether to migrate all at once to distribute data into small chunks. Even if you choose to migrate in smaller chunks, there is always a question of what to shift first?

Apart from these challenges, CTOs also face the challenge of migrating unstructured data within their systems. If the target database supports structured data and massive unstructured data, processing information on such a scale is challenging. 

Solution- Taking cues from Spotify’s cloud migration journey, you can use small sprints to migrate the entire database to the cloud infrastructure. For example, the engineering teams at Spotify migrated 50-70 services per week, prioritized as per need basis. 


Cloud migration challenges are different for every organization, and there is no single solution that will work as one-size-fits-all. From my experience at Simform over the years, there have been six vital aspects of cloud adoption strategy, 

  • Costing
  • Security
  • Compatibility
  • Performance
  • Scalability
  • Flexibility

Formulating the correct cloud adoption strategy and ensuring that these aspects are covered is a challenging task. You will need engineering expertise and skilled professionals that can offer reliable solutions. Simform has proven experience in managing cloud migrations and helping organizations achieve growth with minimal disruptions. 

So, if you are looking for a cloud migration partner to counter these challenges and improve your system performance, Simform is here for you!

Cloud Migration Challenges

Ronak is Tech Lead at Simform with comprehensive experience designing, developing, and implementing software solutions to address complex business issues and provide technical leadership.

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