diff --git a/CHANGELOG.md b/CHANGELOG.md
index 72065f316..e2d1e5c20 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -33,6 +33,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 - Ensure transitions between `inset-shadow-none` and other inset shadows work correctly ([#20208](https://github.com/tailwindlabs/tailwindcss/pull/20208))
 - Ensure explicitly referenced `@source` directories are scanned even when ignored by git ([#20214](https://github.com/tailwindlabs/tailwindcss/pull/20214))
 - Ensure `@source` globs ending in `**/*` preserve dynamic path segments to avoid scanning too many files ([#20217](https://github.com/tailwindlabs/tailwindcss/pull/20217))
+- Canonicalization: don't fold `calc(…)` divisions when the result would require high precision (e.g. `w-[calc(100%/3.5)]` → `w-[calc(100%/3.5)]`, not `w-[28.571428571428573%]`) ([#20221](https://github.com/tailwindlabs/tailwindcss/pull/20221))
 
 ### Changed
 
diff --git a/packages/tailwindcss/src/canonicalize-candidates.test.ts b/packages/tailwindcss/src/canonicalize-candidates.test.ts
index c78d40e76..c01ee78e1 100644
--- a/packages/tailwindcss/src/canonicalize-candidates.test.ts
+++ b/packages/tailwindcss/src/canonicalize-candidates.test.ts
@@ -1244,6 +1244,17 @@ describe.each([['default'], ['with-variant'], ['important'], ['prefix']])('%s',
 
     await expectCanonicalization(input, candidate, expected)
   })
+
+  // https://github.com/tailwindlabs/tailwindcss-intellisense/issues/1591
+  test.each([
+    ['w-[calc(100%/3.5)]', 'w-[calc(100%/3.5)]'], // Not w-[28.571428571428573%]
+  ])(testName, { timeout }, async (candidate, expected) => {
+    let input = css`
+      @import 'tailwindcss';
+    `
+
+    await expectCanonicalization(input, candidate, expected)
+  })
 })
 
 describe('theme to var', () => {
diff --git a/packages/tailwindcss/src/constant-fold-declaration.test.ts b/packages/tailwindcss/src/constant-fold-declaration.test.ts
index c48b64b34..5a0c867b6 100644
--- a/packages/tailwindcss/src/constant-fold-declaration.test.ts
+++ b/packages/tailwindcss/src/constant-fold-declaration.test.ts
@@ -127,3 +127,11 @@ it.each([
 it('should not constant fold when dividing by `0`', () => {
   expect(constantFoldDeclaration('calc(123rem / 0)')).toBe('calc(123rem / 0)')
 })
+
+it('should not constant fold when a computation has a high-precision result', () => {
+  expect(constantFoldDeclaration('calc(100% / 3.5)')).toBe('calc(100% / 3.5)')
+})
+
+it('should constant fold division results with floating-point error after scaling', () => {
+  expect(constantFoldDeclaration('calc(29% / 100)')).toBe('0.29%')
+})
diff --git a/packages/tailwindcss/src/constant-fold-declaration.ts b/packages/tailwindcss/src/constant-fold-declaration.ts
index 7c54ae414..34a746d8e 100644
--- a/packages/tailwindcss/src/constant-fold-declaration.ts
+++ b/packages/tailwindcss/src/constant-fold-declaration.ts
@@ -286,8 +286,19 @@ export function constantFoldDeclarationAst(
               ((lhs[1] === null && rhs[1] === null) || // Unitless / Unitless, e.g.: `8 / 2`
                 (lhs[1] !== null && rhs[1] === null)) // Unit / Unitless, e.g.: `1rem / 2`
             ) {
+              let computed = lhs[0] / rhs[0]
+
+              // Only fold with .xx precision, anything beyond that might be a bit too much.
+              //
+              // E.g. 100% / 3.5 = 28.571428571428573%, which is correct but not
+              //      as user friendly. Especially when going from
+              //      `w-[calc(100%/3.5)]` → `w-[28.571428571428573%]`
+              if (Math.round(computed * 100) / 100 !== computed) {
+                break
+              }
+
               folded = true
-              return WalkAction.ReplaceSkip(ValueParser.word(`${lhs[0] / rhs[0]}${lhs[1] ?? ''}`))
+              return WalkAction.ReplaceSkip(ValueParser.word(`${computed}${lhs[1] ?? ''}`))
             }
             break
           }