A Comprehensive Guide to Seamless Migration: From Legacy to Modern Headless CMS

As technology evolves, maintaining an outdated website can become a significant liability. Many businesses find themselves relying on legacy content management systems (CMS) that, while once cutting-edge, now struggle to keep pace with modern performance expectations, cybersecurity threats, and content delivery optimizations. These older platforms may have served well in the past, growing alongside the organization and becoming deeply integrated into its workflows. However, the aging system can often impede performance, result in security vulnerabilities and a lack of scalability — ultimately hindering innovation and competitiveness.

In contrast, modern web technologies, such as headless CMS architectures, microservices, and cloud-based digital asset management platforms, offer greater flexibility, efficiency, and speed. Migrating to a composable and headless solution is a strategic investment in future-proofing digital infrastructure. This transition allows organizations to leverage modern APIs, streamline content distribution, and enhance user experiences across multiple platforms.

This article provides a comprehensive guide to:

1. Migrating from a custom CMS hosted on AWS to an open-source headless CMS, Strapi.

2. Deploying on Google Cloud with Cloudinary handling asset management. 

By detailing the steps, challenges, and solutions encountered, we aim to provide valuable insights for organizations looking for a seamless migration.

Key Considerations Before Migrating

A website migration is a significant undertaking that requires careful planning and a clear approach. Before beginning such a transition, it is essential to evaluate the current state of your digital presence. Consider the following questions:

• Is your organization's website performance meeting business and user expectations?

• Does your current CMS support modern SEO best practices and ranking factors?

• How frequently is your organization's website refreshed, updated, and optimized?

• Does your CMS seem overly complex due to years of ad-hoc updates and feature additions?

• Is the database structured efficiently, or is it encumbered by excess data?

• Are your organization's resources consumed by constant bug fixes and maintenance rather than innovation?

• Are there critical features your organization wishes to implement but cannot due to technological limitations?

• Is excessive storage usage leading to unnecessary hosting costs?

If the answers to these questions reveal inefficiencies, limitations, or excessive technical debt, a migration to a modern headless CMS could be the optimal solution for your organization. Keeping these factors in mind will help your organization reinforce the decision to migrate, particularly when faced with challenges during the transition process.

Key Benefits of Migrating to a Headless CMS

Concerns about potential disruptions, replatforming complexities, and the risk of losing organic (SEO) traffic often make maintaining the status quo an comfortable  option.. However, the advantages of adopting a headless CMS far outweigh any short-term challenges, as it provides significant benefits across scalability, security, performance, and personalization.

1. Scalability

Unlike traditional CMS platforms, a headless architecture separates the presentation layer from data and compute processes. This allows the front-end to be deployed on serverless content delivery networks, enabling seamless global scalability without the need for additional hosting resources.

As traffic increases, performance remains stable, ensuring a smooth user experience regardless of demand.

2. Enhanced Security

By design, headless CMS implementations minimize security risks because content is delivered via authenticated APIs, while the front-end is often statically generated, significantly reducing attack surfaces. Without a traditional back-end directly exposed to the internet, the risk of cyber threats such as SQL injection, brute force attacks, and plugin vulnerabilities is virtually eliminated.

3. Improved User Experience (UX), Customer Experience (CX), and SEO

Leveraging modern front-end frameworks such as Next.js transforms page performance. Rather than relying on traditional server-side rendering, static site generation (SSG) and incremental static regeneration (ISR) provide near-instantaneous load times. This results in a seamless browsing experience, higher customer satisfaction, improved conversion rates, and enhanced SEO rankings due to superior core web vitals.

4. Advanced Personalization

Integrating a headless CMS with customer data platforms allows for dynamic and highly personalized content experiences. Websites can tailor content and landing pages to individual users or audience segments based on key data points such as industry, organization size, location, or browsing behavior. This level of personalization drives engagement, increases retention, and enhances overall customer interactions.

Laying the Groundwork for Migration

A successful migration requires a strategic and methodical approach, structured protocols and best practices, in order to ensure data integrity and achieve a seamless transition to a headless CMS.

Given the complexity of such projects, a coordinated team effort is essential. Clear communication between team members and stakeholders helps establish alignment on goals, timelines, and technical requirements.

In addition to migrating to a headless CMS, our newly-developed Next.js front-end shows the contribution of each team member working at different stages of the migration process, including the investigative phase, which entails laying the groundwork for a successful transition.

Phase One: Initial Investigation

A thorough discovery phase is critical for understanding the intricacies of the existing CMS and website. Before initiating a migration, the team must develop a comprehensive understanding of:

• The current CMS’s features and functionalities

• The existing website’s infrastructure and architecture

• The database structure, shape and content organization

• Key third-party integrations and dependencies.

Beyond technical discovery, stakeholder interviews can provide valuable insights into how the system is used in practice. Understanding content management workflows, editorial requirements, and pain points ensures that the new CMS meets business needs effectively. Documenting these findings is essential, as overlooking key details can lead to incorrect data mapping or overlooked edge cases during migration.

Selecting the Right Technology Stack

Choosing the appropriate technology stack involves balancing business requirements, costs, and technical capabilities. During one migration project, the client requested feature parity with their existing CMS, a familiar editorial workflow for content managers, and a scalable, customizable solution for future growth. As such, these were the criteria which guided our team's selection process, ultimately resulting in us choosing Strapi as the headless CMS. Strapi’s open-source and self-hostable nature provided several key advantages, including flexibility, cost-effectiveness, and scalability of content management solutions.

One of the most significant benefits of Strapi is its customization and extensibility. As an open-source platform, it allows for deep customization, enabling developers to introduce new features and tailor the CMS to specific project requirements. Unlike proprietary solutions that may impose restrictions, Strapi’s flexibility ensures that unique business needs can be met without compromising on functionality or performance.

Another major advantage is cost control. Because Strapi is self-hosted, organizations can choose their preferred cloud provider, avoiding the vendor lock-in that often comes with SaaS-based CMS platforms. This level of control allows for cost-effective resource allocation, making hosting expenses predictable and manageable. Additionally, self-hosting provides greater oversight of updates and maintenance, reducing the risk of unexpected changes that could disrupt workflows.

Strapi also offers integration flexibility, a crucial factor in modern web development. With its API-first approach, Strapi seamlessly connects with third-party services and microservices. In this project, integrating Cloudinary as the digital asset management (DAM) solution was a key priority. Strapi’s API-driven architecture made this process smooth, allowing for efficient media handling, optimization, and delivery without compromising performance.

Finally, database optimization also played a vital role in our decision. Strapi supports multiple database options, and for this project, we selected PostgreSQL due to its reliability, scalability, and ability to handle structured content efficiently. PostgreSQL offers robust data integrity and supports advanced querying, making it an optimal choice for a modern CMS that requires efficient data management and retrieval.

By leveraging Strapi’s open-source capabilities, cost efficiency, seamless integrations, and strong database support, we ensured a highly adaptable and future-proof CMS infrastructure tailored to the client's needs.

For hosting, we selected Google Cloud Platform (GCP) due to its intuitive interface, cost-efficiency, and robust infrastructure.

On the front end, we adopted Next.js, a widely recognized React meta-framework, so that the website would be highly performant, benefiting from server-side rendering (SSR), static site generation (SSG), and incremental static regeneration (ISR)—all of which contribute to faster load times and enhanced user experience.

With this foundation in place, the next phase was execution: migrating data, implementing the new front-end, and optimizing content workflows within the new headless CMS environment.

Strategic Planning for Data Migration

A critical aspect of the structured migration strategy to ensure a seamless transition from the legacy CMS to Strapi is understanding how existing data will be mapped and structured within Strapi’s predefined architecture. Since Strapi provides a well-documented, out-of-the-box framework with a structured content model, it serves as the foundation for organizing and migrating data efficiently.

The first step in this process is database mapping, which requires analyzing the existing CMS database structure and aligning it with Strapi’s content-type architecture. This is essential for a smooth transition, as improper mapping can lead to data inconsistencies, loss of information, or additional rework during development. 

One of the primary considerations in database mapping is maintaining parity where practical. Ensuring a logical and predictable structure makes it easier for developers and content editors to adapt to the new system, improving workflow efficiency and reducing the learning curve associated with a new CMS.

Another important aspect of this process is eliminating redundant data. The migration process presents an ideal opportunity to audit and clean up the database, removing excess data that has accumulated over time, while ensuring that only relevant and valuable content is carried forward into Strapi.

At the same time, while Strapi is highly flexible, it does not always support a direct one-to-one replication of features from a legacy CMS. Identifying which functionalities may require custom field implementations, alternative data structuring, or additional plugins to achieve the desired outcome in the migration process allows teams to develop workarounds and proactively strategize for any required modifications.

Content Data Modelling

A unique feature of Strapi is its automated relationship model, which differs from traditional CMS platforms that often require extensive manual configuration for content relationships. In Strapi, accounting for these relations between content types which are managed dynamically, can simplify content modeling. Careful planning of Strapi's handling of relational data helps adjust the migration strategy accordingly.
Finally, Strapi’s plugin ecosystem provides various extensions that enhance functionality, from authentication and role management to media handling and data import tools. By maximizing the use of available plugins, organizations can reduce development time, minimize complexity, and enhance overall system capabilities without reinventing the wheel.

By considering these factors - database structure alignment, redundant data removal, Strapi’s technical constraints, automated relationships, and available plugins - the migration process is more structured and efficient. This ensures a seamless transition to Strapi while optimizing performance and maintaining data integrity.

Once the database structure and migration strategy are well-documented, the next step is identifying tools and solutions for executing the migration. Given that Strapi is open source, pre-built migration solutions are limited, particularly when working with a fully custom CMS. We found that developing a custom migration application tailored to our project’s requirements worked best as it was designed to:

1. Extract content from the legacy CMS (Point A)

2. Transform and format the data into JSON

3. Seed it into Strapi (Point B)

4. Additionally, media assets required a separate process, which were uploaded to Cloudinary (Point C) before the corresponding JSON entries were updated in Strapi. 

By taking this approach, all structured content and assets were migrated efficiently while maintaining data integrity.

Proof of Concept and Minimum Viable Product (MVP)

Before any significant progress can be made in migration, the foundational setup must be in place. This includes initializing a new Git repository, ensuring that the latest stable version of Strapi is installed, and setting up a local database to host the Strapi application—this will become the future home of the migrated content. Once these preliminary steps are completed, in addition to strategies, documentation, and theoretical planning, the migration process can begin.

Strapi offers built-in functionality, but depending on project requirements, third-party plugins or custom extensions may be necessary to meet specific needs. For example, Strapi’s default rich text editor proved insufficient for the project due to limited formatting and content management features. To resolve this, we integrated CKEditor 5, a robust and highly customizable text editor, to ensure an enhanced authoring experience for content managers. Installing such dependencies before creating collections and defining content fields within Strapi results in a smooth setup of content collections.

With all necessary plugins and dependencies installed, the next step is executing the database mapping plan previously developed. At this stage, the structured content model in Strapi is built using Collection Types, Single Types, and Components. Since Strapi provides an intuitive UI for structuring collections and defining content fields, this phase should be relatively straightforward, especially if the mapping documentation was thoroughly prepared in advance. This is a crucial part of ensuring that the new CMS accurately reflects the original data structure while optimizing for efficiency.

Once the content schema is established in Strapi, the focus shifts to the actual content migration process. At this point, the dashboard may appear empty, prompting several critical questions:

• How do we efficiently transfer content from the legacy CMS to Strapi?

• How do we provide real, structured data for the frontend development team to begin their work?

• How do we validate whether the migration strategy is effective before committing to a full-scale data transfer?

To address these challenges, we developed a custom migration application. This tool facilitated the transfer of content from the legacy CMS (Point A), transformed the data into JSON format, and then seeded it into Strapi (Point B). Additionally, media assets followed a separate workflow, requiring them to be uploaded to Cloudinary (Point C) before updating their references in Strapi. By taking this approach, the content was not only transferred accurately but also optimized for future scalability.
A deeper technical breakdown of this structuring, testing process, and the coordination between frontend developers, clients, and internal teams, provides some key insights from the migration process, including:

• Preparing for extensive debugging by expecting to spend considerable time sifting through console logs and error notices. A comfortable IDE theme and a well-structured logging system will be your best allies.

• Testing migrations in smaller batches rather than attempting a full data migration in one go, start with small datasets to identify potential issues early and prevent catastrophic failures.

• Accounting for edge cases, with no two data entries are the same. Testing with a single dataset is insufficient; thorough validation across multiple content types ensures that the migration process is resilient against unexpected variations.

With content flowing from Strapi into the frontend application, the project begins to take shape. At this stage, a functional demonstration is essential. Showcasing the MVP allows for early feedback, identifies areas needing refinement, and ensures that the migration strategy aligns with the client’s expectations. At this point, the entire team - developers, designers, and stakeholders - assesses progress and critiques the implementation, evolving from a raw technical migration into a refined, production-ready CMS solution that delivers scalability, flexibility, and an enhanced user experience.

Demo, Client Feedback, and Finalizing

At this stage of the migration process, clients, naturally, want to see tangible progress on the product they are investing in, and that their vision is materializing as expected. Receiving and incorporating client feedback is essential to keeping the project aligned with their expectations and preventing unnecessary refactoring later. At this stage, a stable Strapi instance with a representative dataset populated from their existing site should now be demonstrable. This milestone serves as a critical checkpoint, enabling stakeholders to assess the migration progress, identify gaps, and provide insights that will help refine the final product.

The period leading up to a demonstration can be demanding, but it is also a crucial validation of the work invested in the migration process. Thorough preparation is essential: all necessary browser tabs should be readily accessible, alternative content should be preloaded, user flows should be rehearsed, and potential client inquiries should be anticipated. By this stage, the dataset within Strapi should be sufficiently developed to facilitate a seamless demonstration, allowing the focus to remain on showcasing key functionalities rather than drawing attention to incomplete content or placeholders. Furthermore, as the individual overseeing the data migration, a comprehensive understanding of Strapi’s architecture and the specific implementation will be critical in providing clear, confident explanations. 

Following the demonstration, it is essential to move beyond feedback from a guided walkthrough by providing the client with access to a test environment. This enables them to explore the system independently, engaging with the CMS in a real-world context rather than through the lens of a developer. Encouraging the client to interact with the platform in this way is crucial for identifying any remaining usability challenges, pain points, or unexpected issues that may not have emerged during structured testing. The insights gained from this process offer valuable, practical feedback that informs the final refinements before full deployment.

If everything has gone according to plan, this phase should yield constructive feedback rather than fundamental concerns. By this point, the extensive planning, thorough documentation, strategic mapping, and clear communication should show the client that they made the right choice in trusting the team with this migration. Their vision should now be taking shape, and internally, the development team should begin to see the finish line approaching. 

The final phase involves completing the content migration, ensuring that all remaining structured data and media assets are seamlessly integrated into their new home. While migrating raw content is one challenge, handling assets - including images, videos, and downloadable files - also requires carefully ensuring a smooth final transition into production.

Asset Transfer

Regardless of where the assets are currently stored, the migration process involves locating the assets, transferring them to a new destination, and updating all references to reflect their new URLs. This often involves extensive regular expression (Regex) work to create a seamless transition. In our case, the migration involved transferring assets to Cloudinary, a powerful Digital Asset Management (DAM) platform known for its advanced media handling capabilities.

Cloudinary offers multiple approaches to asset migration, all of which are documented in their official Migration Guide. However, the first and most critical step is evaluating the scale of the migration. When dealing with a large volume of assets (for example, 150,000 images and files, scattered across structured image fields and rich text content), it is preferred to have a migration script. The actual transfer process, while lengthy, is relatively straightforward: 1) Identify asset locations; 2) Request Cloudinary to fetch them, and 3) Record the new asset details within the CMS. Fortunately, Strapi offers a Cloudinary integration plugin via the Strapi Marketplace, which helps facilitate a smooth connection between the two systems. However, the more complex challenge is mapping the newly generated Cloudinary URLs back to their respective locations in Strapi.

A detailed breakdown of the methodology, challenges, and problem-solving techniques used during the asset migration process is as follows:

1. If a specific URL structure is needed, Cloudinary must configure it manually.

2. Large migrations can take hours, so breaking the process into multiple sessions is advisable.

3. Using service workers or multiple scripts enables concurrent asset transfers for faster migration.

4. Cloudinary charges based on storage and transfer volume, potentially leading to significant expenses.

5. All assets must be migrated first to prevent broken image links in content.

6. Logging errors ensures failed uploads can be diagnosed and retried efficiently.

7. Keeping track of success rates, failures, and remaining assets is essential for accurate progress reporting.

8. Both structured data and embedded media in rich text fields must have updated asset references.

Code Example

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// Uploading to Cloudinary
const uploadToCloudinary = async (image) => {
  // Sset up cloudinary config
  const cloudinaryOptions = {
    tags: "migration",
    overwrite: false,
    unique_filename: false,
    use_filename: true,
  };

  // Set up promise for upload
  return new Promise((resolve, reject) => {
    // Upload image to cloudinary
    cloudinary.uploader.upload(image, cloudinaryOptions, (err, url) => {
      if (err) return reject(err);
      return resolve(url);
    });
  });
};

const uploadMedia = async () => {
  // Get all assets from the your host
  const assets = await getAssets();
  const cloudinaryResp = {};

  // Set up object that will be written to a file
  const seedJSON = [];
  const seedJSONErrors = [];

  // Iterate through each asset
  for (const asset of assets) {
    // Trigger upload to cloudinary
    try {
      const data = await uploadToCloudinary(asset.remoteAddress);
      cloudinaryResp = {
        ok: true,
        data,
      };
    } catch (error) {
      cloudinaryResp = {
        ok: false,
        error,
      };
    }

    // Check if the upload was successful
    if (!cloudinaryResp.ok) {
      seedJSONErrors.push(cloudinaryResp.error);
    }

    // Add the asset to the seedJSON object
    seedJSON.push(cloudinaryResp.data);
  }

  // Write the seedJSON objects to a file
  writeProcessedJSON("./data", "assets", "json", JSON.stringify(seedJSON));
  writeProcessedJSON(
    "./data",
    "assetsErrors",
    "json",
    JSON.stringify(seedJSONErrors)
  );
};

Given the granular nature of asset migrations, this step should be treated as a separate mini-project within the broader CMS transition. Maintaining detailed tracking logs is critical to ensuring that every asset is accounted for. 

A poorly managed migration can result in missing images or broken links, forcing a frustrating re-run of the entire process to correct mistakes.

Once all assets are successfully transferred, mapped, and validated by the client, the final migration phase begins. At this stage, the legacy CMS is frozen, preventing any further content modifications.

Deployment

At this stage of the migration process, precision and coordination are critical. The entire team must work cohesively to complete final checks before deployment. A well-structured plan minimizes the risk of errors and creates a seamless transition from the legacy system to the new environment. 

The order of deployment operations is essential, as missteps can lead to delays, data inconsistencies, or significant disruptions to the project timeline. The first step is securing the final database transfer from the legacy CMS before the system is fully retired. Simultaneously, it is essential to confirm that all assets have been successfully transferred and accounted for in Cloudinary, and all edge cases have been addressed before proceeding with the final migration. At this stage, the scale of the migration becomes evident, as the content volume grows significantly from the initial sample size. 

A key consideration is how to move the data from the local migration environment to the hosted production database across multiple environments. Namely, before executing the final migration, several critical checks must be completed:

• The databases are fully configured and tested

• All necessary credentials and permissions align with the target environments

• The local instance has been validated for compatibility with the hosted database.

The approach to deployment varies depending on the scale of the project. For smaller migrations, direct population of the production database from the local source may be a viable option. However, for large-scale projects, this method can introduce significant risks. A more controlled approach involves creating and validating the database locally before migrating it to the designated environments (Production, Staging, and Development). This allows for issue resolution before deployment, reducing potential setbacks.

With all elements in place, the final migration is considered complete when the content is populated in both Staging and Production environments, and the frontend application successfully integrates the newly migrated data. After thorough verification and final client approval, the new system goes live, and the migration process from the legacy CMS to Strapi is finalized. 

Conclusion

A successful migration is the result of meticulous planning, coordination, and execution. As demonstrated in this article, migrating a CMS involves a complex series of steps, each requiring careful attention to detail. While moving content from one system to another may seem straightforward, challenges arise in execution—handling asset volume, restructuring content, managing hosting, and ensuring a seamless transition all demand strategic foresight.

Success depends on a well-coordinated team with a clear vision of the end goal. Anticipating obstacles, refining processes, and adapting to unforeseen challenges ensure a smooth transition. While the process may be time-consuming, a well-executed migration ensures long-term stability and efficiency, eliminating the need for costly and time-intensive rework.