diff --git a/CHANGELOG.md b/CHANGELOG.md
index 9e62f00b5122..b7304af6781c 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -17,6 +17,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 - _Upgrade (experimental)_: Fully convert simple JS configs to CSS ([#14639](https://github.com/tailwindlabs/tailwindcss/pull/14639))
 - _Upgrade (experimental)_: Migrate `@media screen(…)` when running codemods ([#14603](https://github.com/tailwindlabs/tailwindcss/pull/14603))
 - _Upgrade (experimental)_: Inject `@config "…"` when a `tailwind.config.{js,ts,…}` is detected ([#14635](https://github.com/tailwindlabs/tailwindcss/pull/14635))
+- _Upgrade (experimental)_: Migrate `aria-*`, `data-*`, and `supports-*` variants from arbitrary values to bare values ([#14644](https://github.com/tailwindlabs/tailwindcss/pull/14644))
 
 ### Fixed
 
diff --git a/packages/@tailwindcss-upgrade/src/template/codemods/arbitrary-value-to-bare-value.test.ts b/packages/@tailwindcss-upgrade/src/template/codemods/arbitrary-value-to-bare-value.test.ts
new file mode 100644
index 000000000000..2f29c130fb67
--- /dev/null
+++ b/packages/@tailwindcss-upgrade/src/template/codemods/arbitrary-value-to-bare-value.test.ts
@@ -0,0 +1,31 @@
+import { __unstable__loadDesignSystem } from '@tailwindcss/node'
+import { expect, test } from 'vitest'
+import { arbitraryValueToBareValue } from './arbitrary-value-to-bare-value'
+
+test.each([
+  ['data-[selected]:flex', 'data-selected:flex'],
+  ['data-[foo=bar]:flex', 'data-[foo=bar]:flex'],
+
+  ['supports-[gap]:flex', 'supports-gap:flex'],
+  ['supports-[display:grid]:flex', 'supports-[display:grid]:flex'],
+
+  ['group-data-[selected]:flex', 'group-data-selected:flex'],
+  ['group-data-[foo=bar]:flex', 'group-data-[foo=bar]:flex'],
+  ['group-has-data-[selected]:flex', 'group-has-data-selected:flex'],
+
+  ['aria-[selected]:flex', 'aria-[selected]:flex'],
+  ['aria-[selected="true"]:flex', 'aria-selected:flex'],
+  ['aria-[selected*="true"]:flex', 'aria-[selected*="true"]:flex'],
+
+  ['group-aria-[selected]:flex', 'group-aria-[selected]:flex'],
+  ['group-aria-[selected="true"]:flex', 'group-aria-selected:flex'],
+  ['group-has-aria-[selected]:flex', 'group-has-aria-[selected]:flex'],
+
+  ['max-lg:hover:data-[selected]:flex!', 'max-lg:hover:data-selected:flex!'],
+])('%s => %s', async (candidate, result) => {
+  let designSystem = await __unstable__loadDesignSystem('@import "tailwindcss";', {
+    base: __dirname,
+  })
+
+  expect(arbitraryValueToBareValue(designSystem, {}, candidate)).toEqual(result)
+})
diff --git a/packages/@tailwindcss-upgrade/src/template/codemods/arbitrary-value-to-bare-value.ts b/packages/@tailwindcss-upgrade/src/template/codemods/arbitrary-value-to-bare-value.ts
new file mode 100644
index 000000000000..065f10807326
--- /dev/null
+++ b/packages/@tailwindcss-upgrade/src/template/codemods/arbitrary-value-to-bare-value.ts
@@ -0,0 +1,94 @@
+import type { Config } from 'tailwindcss'
+import { parseCandidate, type Candidate, type Variant } from '../../../../tailwindcss/src/candidate'
+import type { DesignSystem } from '../../../../tailwindcss/src/design-system'
+import { segment } from '../../../../tailwindcss/src/utils/segment'
+import { printCandidate } from '../candidates'
+
+export function arbitraryValueToBareValue(
+  designSystem: DesignSystem,
+  _userConfig: Config,
+  rawCandidate: string,
+): string {
+  for (let candidate of parseCandidate(rawCandidate, designSystem)) {
+    let clone = structuredClone(candidate)
+    let changed = false
+    for (let variant of variants(clone)) {
+      // Convert `data-[selected]` to `data-selected`
+      if (
+        variant.kind === 'functional' &&
+        variant.root === 'data' &&
+        variant.value?.kind === 'arbitrary' &&
+        !variant.value.value.includes('=')
+      ) {
+        changed = true
+        variant.value = {
+          kind: 'named',
+          value: variant.value.value,
+        }
+      }
+
+      // Convert `aria-[selected="true"]` to `aria-selected`
+      else if (
+        variant.kind === 'functional' &&
+        variant.root === 'aria' &&
+        variant.value?.kind === 'arbitrary' &&
+        (variant.value.value.endsWith('=true') ||
+          variant.value.value.endsWith('="true"') ||
+          variant.value.value.endsWith("='true'"))
+      ) {
+        let [key, _value] = segment(variant.value.value, '=')
+        if (
+          // aria-[foo~="true"]
+          key[key.length - 1] === '~' ||
+          // aria-[foo|="true"]
+          key[key.length - 1] === '|' ||
+          // aria-[foo^="true"]
+          key[key.length - 1] === '^' ||
+          // aria-[foo$="true"]
+          key[key.length - 1] === '$' ||
+          // aria-[foo*="true"]
+          key[key.length - 1] === '*'
+        ) {
+          continue
+        }
+
+        changed = true
+        variant.value = {
+          kind: 'named',
+          value: variant.value.value.slice(0, variant.value.value.indexOf('=')),
+        }
+      }
+
+      // Convert `supports-[gap]` to `supports-gap`
+      else if (
+        variant.kind === 'functional' &&
+        variant.root === 'supports' &&
+        variant.value?.kind === 'arbitrary' &&
+        /^[a-z-][a-z0-9-]*$/i.test(variant.value.value)
+      ) {
+        changed = true
+        variant.value = {
+          kind: 'named',
+          value: variant.value.value,
+        }
+      }
+    }
+
+    return changed ? printCandidate(designSystem, clone) : rawCandidate
+  }
+
+  return rawCandidate
+}
+
+function* variants(candidate: Candidate) {
+  function* inner(variant: Variant): Iterable<Variant> {
+    yield variant
+    if (variant.kind === 'compound') {
+      yield* inner(variant.variant)
+    }
+  }
+
+  for (let variant of candidate.variants) {
+    yield* inner(variant)
+  }
+}
diff --git a/packages/@tailwindcss-upgrade/src/template/migrate.ts b/packages/@tailwindcss-upgrade/src/template/migrate.ts
index df9d22b15af8..50f2ca60e87f 100644
--- a/packages/@tailwindcss-upgrade/src/template/migrate.ts
+++ b/packages/@tailwindcss-upgrade/src/template/migrate.ts
@@ -3,6 +3,7 @@ import path, { extname } from 'node:path'
 import type { Config } from 'tailwindcss'
 import type { DesignSystem } from '../../../tailwindcss/src/design-system'
 import { extractRawCandidates, replaceCandidateInContent } from './candidates'
+import { arbitraryValueToBareValue } from './codemods/arbitrary-value-to-bare-value'
 import { automaticVarInjection } from './codemods/automatic-var-injection'
 import { bgGradient } from './codemods/bg-gradient'
 import { important } from './codemods/important'
@@ -22,6 +23,7 @@ export const DEFAULT_MIGRATIONS: Migration[] = [
   automaticVarInjection,
   bgGradient,
   simpleLegacyClasses,
+  arbitraryValueToBareValue,
   variantOrder,
 ]