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6 Crucial Issues for Legacy .NET App Modernization

Author: Sambit Ghosh | | April 6, 2022


You’ve decided that you’re ready to embark on a modernization project for your legacy .NET applications—but making that decision is only the first step. Along the way, you’ll likely experience difficulties and pitfalls that threaten to derail your modernization initiative.

In the face of these challenges, your business needs to be well-prepared for what lies ahead. Below, we’ll discuss 6 of the essential issues and factors that organizations need to consider when refreshing their legacy .NET apps.

1. Identifying your business priorities

While you might be passionate about the cause of modernizing legacy tech, it’s important not to bite off more than you can chew. The first step is to select the business capabilities and strategies that are most important to you, and then focus on the underlying technology that supports them.

Here, a technique known as capability indexing can be a tremendously valuable place to start. In capability indexing, users assess the ability of a process or system to fulfill their business specifications and requirements along three axes: the best-case scenario, the worst-case scenario, and the “average” or typical case.

2. Understanding what’s in front of you

The next step is to break down the legacy .NET apps that you’re targeting for modernization, and to understand them on a technical level. This should include asking questions like:

  • What is the system architecture?
  • Where is the source code stored?
  • How is the application compiled and packaged?
  • What are the application’s libraries, dependencies, and settings?


Answering these questions will be crucial to knowing what’s possible and what should be done with your modernization project.

3. Considering new ideas

Legacy applications create pain points because they hold the organization back from innovation in other technologies as well. In other words, modernizing your legacy .NET apps is the perfect chance for your business to modernize other aspects of your IT environment.

For example, refreshing your .NET applications makes it much easier to adopt modern IT best practices such as cloud computing and microservices. You can also take this opportunity to implement new methodologies such as DevOps and agile that help make your IT teams more productive and efficient.

In addition to modernizing your .NET applications and development methodologies, you might also take this chance to renovate the underlying database, or fix chronic pain points such as data quality issues. This could include changes to the database’s software, architecture, data schema, or security practices.

4. Selecting the right metrics

If you’re planning to launch major IT initiatives such as legacy app modernization, you need to have a way to measure their success. Before you begin, make sure you choose the most informative metrics and key performance indicators (KPIs), so that you can track the project from onset to completion and beyond.

The right metrics will depend on your primary motivations for your .NET refresh: are you looking to increase revenue, boost your customer satisfaction rates, improve system uptime, or something else entirely? For example, by how much is the modernization project expected to reduce your IT costs? In particular, migrating to the Microsoft Azure cloud will shift from a capital expense to an operational expense, and can help save on hardware, software, and maintenance.

Data security, too, can be a crucial business metric. If your legacy technology is past its end of life, there may be serious unpatched vulnerabilities that malicious actors can exploit. You can run security scans on the legacy system before and after the migration, counting the number of issues detected to make sure that you’ve patched any holes.

5. Thinking big (and far)

It can be tempting for companies to go with the latest, greatest technologies when modernizing their legacy applications. However, you need to ensure that your updated software will remain compatible with the rest of your IT environment.

Often, a “less is more” approach can serve you well: start with implementing the most business-critical features, and then gradually expand the software’s functionality. You should also consider whether your choice of technology stack will be able to provide solid performance and an appealing user experience now and into the future.

6. Establishing an IT culture

Modernizing legacy applications is the perfect opportunity to reform your broader IT and engineering culture as well. If you don’t future-proof your IT environment, it’s likely that you’ll be in the same position 5, 10, or 20 years down the line—when today’s cutting-edge advances have become a new generation of “legacy” tech.

To guard against this possibility, make sure that you foster an IT-first mindset among managers, executives, and other key decision-makers. Consider establishing internal coding standards that will make testing and long-term maintenance easier. Practices such as continuous integration/continuous deployment (CI/CD), test-driven development, and cloud-native development will make it easier for programmers to reduce their technical debt and stay ahead of the curve.


With so many factors to keep track of, it can be intimidating for businesses to set off on their app modernization journey. The good news is that updating your legacy .NET software is much smoother when you work with a skilled, trusted modernization partner like Datavail.

Datavail is a Microsoft Gold Partner with a long list of competencies: application development, application integration, cloud platforms, cloud productivity, data analytics, and more. With over 15 years of experience in data platform and application development, and an average partnership length with our clients of more than 7 years, we have the expertise your business needs to make your .NET modernization project a long-term success.

Looking to move your legacy .NET apps to the Microsoft Azure cloud? We can help. Get in touch with Datavail’s team of appdev experts today for a chat about your unique situation. To learn more about the most important challenges and concerns when modernizing your .NET apps, you can also download our white paper “Legacy .NET Application Modernization with Microsoft Azure.”

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