Top application modernization challenges & how spec-driven development is the answer

Undocumented and tangled codebases

Most legacy applications run on outdated, undocumented code. They are built on programming styles inconsistent with the individual or organization’s modern standards - the product of many years of handovers from one developer to another.

Limited documentation makes it difficult for new developers to grasp the code’s architectural context, increasing post-deployment maintenance costs. Approximately 40% of infrastructure systems across asset classes have technical debt concerns, according to Gartner.

Legacy infrastructure dependencies

Legacy systems typically operate on niche licensing or without any licensing at all. That means legacy users often receive minimal or no security updates, technical support, and general quality of life improvements. Many vendors also charge a premium to keep supporting legacy software, regularly increasing fees without offering anything new in return.

Containerization is an effective way to migrate legacy applications to the cloud, while eliminating vendor lock-in and unlocking cloud native capabilities. Incrementally migrating legacy applications to the cloud, via the Strangler Fig Pattern, allows legacy users to gradually replace pieces of functionality with new applications and services with minimal risk.

Outdated frameworks and languages

Outdated frameworks and languages may be incompatible with modern application standards, including API integration and microservices architecture. This makes it difficult to migrate applications running on legacy languages to embrace cloud native functionalities.

As programmers age and move on to different projects and organizations, their legacy framework and language knowledge follow them. These talent and skill gaps make it difficult to maintain applications running on legacy frameworks and knowledge.

Missing or inadequate documentation

Legacy developers who never documented their code risk making it harder for new developers to manage and update their work. Without comments and documentation, new developers must devote additional time and resources to understanding the decisions behind the code.

Discovery sprints, architectural mapping, and technical archeology are three effective ways to address missing or inadequate documentation. Discovery sprints are week-long sessions dedicated to addressing at least one or more substantial risks in your product’s definition. The benefits of completing discovery sprints include challenging assumptions, bringing on early expertise, and defining, refining, and even expanding briefs.

Integration and architectural challenges

Integration and architectural challenges occur when software applications, old and new, encounter communication difficulties. Early intervention makes it easier for development teams to know what to do before writing code.

Integrating legacy systems with modern architecture

Old systems and new systems speak different languages. COBOL (common business-oriented language), a legacy language used in core government and private sector functions, can handle huge processing volumes but has wordy syntax and slow compilation times.

However, economic pressures and a declining pool of COBOL developers have caused many government and private organizations to migrate to Java to integrate with modern cloud-native applications.

Middleware and API layers, as well as ESBs (Enterprise Service Buses), help bridge the gap between legacy and modern systems. Middleware and API layers help facilitate communication and data transfer between disparate platforms, while ESBs help integrate multiple enterprise applications and systems with different protocols and data formats.

Data migration complexity

Migrating data from one environment to another poses a number of issues related to data volume, format differences, and potential data loss during transfer. Mixed data ownership, where multiple teams and units are responsible for different data groups, may necessitate more complex technical planning and coordination overhead.

Reconciling records, encrypting data in transit, and parallel testing are effective ways to combat data migration complexity. Data reconciliation compares data sources, ensuring consistency and accuracy. Data encryption converts plaintext data into unreadable ciphertext, preventing unauthorized access in transit.

Avoiding ‘Cloud Shock’ lift-and-shift without transformation

Lift-and-shift is a popular and cost-effective approach to application modernization. It involves migrating on-site legacy systems to the cloud while retaining their core code and functionality. ‘Cloud shock’ is when individuals and organizations realize the cost of cloud hosting is higher than they envisioned.

True modernization prioritizes architectural transformation over infrastructure migration. It involves investing in more effective, long-term solutions, including factoring and rebuilding.

The 6R decision framework

Below are the six most commonly used modernization strategies:

• Retire - Decommission an application that is no longer needed.
• Retain - Continue to use critical applications as they are until they need refactoring.
• Rehost - Also known as the ‘lift-and-shift’ approach, where an application is migrated to the cloud with minimal changes.
• Replatform - Optimize applications to run in the cloud without changing the core application code and architecture.
• Refactor - Re-architect applications to be cloud-native, typically done through containerizing workloads or moving them to serverless architectures.
• Repurchase - Switch from the license of one SaaS (Software-as-a-Service) model to the license of another SaaS model.

Change resistance

Legacy programmers with years, possibly even decades, of experience may resist the idea of migrating to modern frameworks and languages. Transparent communication, early intervention with skeptics, and demonstrating quick value (through MVPs) can help ease doubts and concerns about the unknown.

At Orient Software, we regularly develop MVP’s to quickly demonstrate the commercial value and potential ROI of business ideas. Our viable, cost-effective solutions help demonstrate the tangible and intangible benefits of your application modernization - minus the risk of entering full production.

Skill gaps

There’s currently a huge expertise shortage in modern technologies, including cloud and AI. 94% of leaders face AI-critical skill shortages, with one in three reporting gaps of 40% or more, according to a global survey of 1,010 C-suite executives.

Cross-training, seeking external expertise (during transition), and setting realistic expectations for teams learning new patterns can help address skill gaps. For example, cross-training involves having star performers train new developers on best practices. By passing down knowledge of legacy frameworks and languages to future generations, they can more effectively maintain on-site and hybrid environments.

Competing priorities and bandwidth

According to research, 44% of individuals cite competing priorities as a common barrier, with 42% of organizations citing the same reason. Competing priorities and bandwidth make it difficult to manage legacy systems and modernize at the same time.

Separating teams into dedicated maintenance and modernization groups can help manage competing priorities. This involves a well-considered change management plan, where your transformation initiative considers not just your technology and processes but also your people.

Mapping dependencies can also help by visually showing teams what systems are communicating with one another, providing a ‘big picture’ overview of every interaction and result.

Cost underestimation

Legacy application modernization and cloud migration projects can quickly spiral out of control. They can cost anywhere from 30,000 USD to 300,000 USD, depending on the enterprise size and project scale.

Training and upskilling, refactoring old applications, and compliance are common hidden cloud migration costs. The cost of running two parallel groups (maintenance and modernization) can also inflate cloud migration budgets.

Budget for technical clean-up time to avoid cost underestimation. Use online calculators to gain realistic estimations based on application source-to-destination pathways, timeline, server, and data volume, and strategy (e.g., lift-and-shift, refactor). Also factor in the cost of migration tools, refactoring licenses, and licensing for cloud-native applications.

ROI uncertainty

ROI uncertainty often stems from an unclear definition of success. It fails to define the key metrics you need to measure in order to precisely achieve results. The result? Unclear roadmaps, constantly-changing priorities, and frustrated teams.

Define the measure outcomes that matter to your business. Set precise goals related to time to market, cost per deployment, and system availability (uptime). At Orient Software, we can develop an MVP that helps you better understand the potential ROI on your idea. This gives you the knowledge and confidence to either move ahead or to step back, re-evaluate, and return with a different approach.

Compliance and security exposure

Most legacy systems do not meet today’s compliance standards, including the GDPR in Europe and the CCPA in the United States. Therefore, the continued operation of legacy systems incurs compliance debt, where the gap between what the system can do and what current regulations want it to do increases slowly.

Shift-left security, early threat modeling, and the principle of least privilege help ensure modernized applications comply with current standards. Shift-left security integrates security early into development, enabling early vulnerability and misconfiguration correction. Automated threat modeling solutions can achieve a 49% reduction in security vulnerabilities during the development phase.

Vendor lock-in

Vendor lock-in occurs when the functionality and security of your software applications are tied to a single vendor. This makes it difficult for you to switch vendors, as doing so typically results in high cancellation and license transfer fees, potential business disruption, and labor or skills shortages for potential new vendors. The result is that you stick with the same vendor even if they do not best meet your needs.

Smart IT vendor management can help. Multi-cloud or hybrid cloud strategies are an effective way to gradually move away from individual vendors. By reducing your dependence on a single vendor, you gradually regain control over your infrastructure and the flexibility to choose more cost-effective and tailored solutions.

It is worth noting that switching from a legacy vendor to a cloud vendor does not equate to modernization. It simply means you have changed hosting environments, otherwise known as the ‘lift-and-shift’ approach. You can still move an outdated application from an on-site environment to a cloud environment, and encounter the same issues you had before the move.

What a specification is (and is not)

Specifications capture what a software application does, the definition of a successful deployment, and the boundaries that the application must not cross. Specifications do not represent past beliefs, coding standards, or one-time deliverables. They evolve with projects, acting as a singular truth source for the application’s entire lifecycle.

How the spec addresses each challenge category

Use the table below to understand the benefits of governing specifications for different challenge categories.

Two practical paths to spec-driven modernization

• Path 1 (for apps 5-10 years old) - Define whether the system is losing clarity, where legacy knowledge is drifting and declining, and if it still provides the necessary information for a governing spec. Define the system’s value, verify its value with evidence, and decide what to change.
• Path 2 (for apps 10+ years old) - If previous modernization attempts have stalled or failed, determine if any approach can be trusted to break the cycle, not restart it.

These paths help identify which challenges are most relevant and determine which starting point makes the most sense.