This guide walks through a structured approach to upgrading Webpack, addressing common challenges, and optimizing your configuration for success.
In the ever-evolving landscape of web development, keeping tools and dependencies up to date is crucial for maintaining performance, security, and compatibility. Recently, I embarked on the journey of upgrading Webpack in one of our major projects. What made this experience unique was my collaboration with Generative AI, specifically ChatGPT. This post chronicles our interactive journey—highlighting the challenges, problem-solving process, and the ultimate success in deploying the upgraded solution to production.
Our project relied on Webpack version 4, and because of a dependency vulnerability it was clear we needed to upgraded. However, upgrading between major versions of Webpack is seldom straightforward. Potential breaking changes, deprecated features, and compatibility issues with loaders and plugins were all on the table.
I decided that I would take a unique approach to this situation and turned to ChatGPT to assist me through the process.
Initially, I wanted to ask ChatGPT for a clean way to upgrade from uglifyjs to terser, which is the new name for the minification plugin for Webpack.
The response, as shown, suggested how I should go about moving from uglifyjs to terser, and although the initial implementation didn’t work as expected, this opened the door to an iterative process. I would provide ChatGPT with error messages, and it would respond with potential solutions.
Although the AI’s suggestions weren’t always perfect, they often pointed me in the right direction, helping me identify gaps in my understanding or configuration.
As I progressed, I kept an ongoing chat with ChatGPT, allowing it to retain the history of our exchanges. This was particularly helpful because our project used two separate Webpack configuration files: one for scripts and one for client-specific themes. Suggested changes that improved one configuration occasionally broke the other, though this was not found until several changes had been made to produce a satisfactory build.
Thanks to good Git practices, I could easily roll back to previous clean commits, test alternative solutions, and move forward when confident. In retrospect, providing ChatGPT with both configurations upfront might have yielded better initial suggestions. However, the iterative approach encouraged me to remain critical of the changes and to fully understand their implications before implementing them.
After multiple iterations over the course of a few days, I was able to successfully build both our Scripts and Themes libraries, and I was able to test everything locally with great success. An unexpected but welcome bonus was a dramatic reduction in build times—from over 30 minutes to less than 1 minute. The credit for this improvement lies somewhere between the Webpack upgrade itself and the collaborative problem-solving process with ChatGPT.
With local tests passing, the final steps involved ensuring that the correct versions of tools were installed on the build server and addressing some unrelated issues caused by our folder structure. Once the PR was merged, the build pipeline completed successfully, and we deployed the changes to our lower environments. Everything worked cleanly, and our project was officially building with Webpack version 5!
While forums like Stack Overflow are invaluable for resolving generic issues, project-specific challenges often require a more tailored approach. Using ChatGPT allowed me to steer the conversation toward our specific setup and constraints without repeatedly justifying non-standard practices.
Overall, the project was a success—not just because the Webpack upgrade was completed, but because the journey was collaborative, educational, and less stressful than it could have been.
The success of this project has highlighted several important lessons and opportunities for future endeavours. Generative AI tools like ChatGPT have proven to be more than just tools for answering isolated questions; they can act as collaborative partners in complex, iterative tasks. In future projects, integrating AI assistance earlier in the process could help leverage its contextual understanding and streamline problem-solving.
This experience also reaffirmed the importance of clear documentation—not just for human collaborators but also for AI. Providing comprehensive context and maintaining detailed records of configurations, decisions, and challenges can lead to faster and more accurate solutions. Documentation remains a cornerstone of effective collaboration, whether the partner is human or AI.
The iterative process of trial, error, and learning was crucial to the success of this upgrade. Iterative problem-solving, paired with ChatGPT’s ability to quickly generate ideas and alternatives, is a powerful combination that I plan to continue using. Balancing this with human oversight ensures that decisions are not just expedient but also well-informed.
Looking beyond this project, I see opportunities to expand the use of Generative AI into other areas of development. From debugging complex issues to planning testing strategies or even contributing to broader architectural discussions, the potential for AI to enhance software development workflows is immense. This project has only scratched the surface of what’s possible.
Finally, this experience has underscored the importance of balancing trust in AI’s recommendations with rigorous verification. While AI can provide valuable insights and guidance, maintaining a critical eye and validating changes ensures high-quality outcomes. As we continue to explore the intersection of human expertise and AI collaboration, this project serves as a reminder of the progress we can achieve when we embrace new tools with care and curiosity.
By reflecting on these considerations, we can carry forward the lessons learned from this journey into future challenges, continuing to improve not only our technical skills but also the ways we collaborate with emerging technologies.
This is a reminder that sometimes the best upgrades aren’t in our tools, it's in the way we improve and enhance how we collaborate.