paid-only post Oct 04, 2026 Frontend

Upgrading three Tailwind projects to v4 in one sprint

I upgraded three client sites to Tailwind v4 in one week. Most utilities survived quietly. The custom gradient border plugin did not.

Why I upgraded three sites in the same week

I had three client projects on Tailwind 3.x that all needed new features in the same sprint. Tailwind v4 was out, the new engine looked fast enough to justify the risk, and I did not want to maintain two different utility dialects for long.

So I blocked a week and upgraded all three in one go. This is what actually mattered: the utilities that kept working, the custom pieces that did not, and the order that made it survivable.

The order: simple static, then shared design system, then the weird one

The main decision was to pick an order that let me learn on a safer codebase and reuse that knowledge on the more fragile ones.

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