diff --git a/packages/@tailwindcss-cli/src/commands/build/index.ts b/packages/@tailwindcss-cli/src/commands/build/index.ts
index eabd2a1de022..c7bd85c5c938 100644
--- a/packages/@tailwindcss-cli/src/commands/build/index.ts
+++ b/packages/@tailwindcss-cli/src/commands/build/index.ts
@@ -22,6 +22,7 @@ import {
   println,
   relative,
 } from '../../utils/renderer'
+import { pathsEqual } from '../../utils/paths-equal'
 import { drainStdin, outputFile } from './utils'
 
 const css = String.raw
@@ -257,7 +258,7 @@ export async function handle(args: Result<ReturnType<typeof options>>) {
         try {
           // If the only change happened to the output file, then we don't want to
           // trigger a rebuild because that will result in an infinite loop.
-          if (files.length === 1 && files[0] === args['--output']) return
+          if (files.length === 1 && pathsEqual(files[0], args['--output']!)) return
 
           using I = new Instrumentation()
           DEBUG && I.start('[@tailwindcss/cli] (watcher)')
@@ -274,7 +275,7 @@ export async function handle(args: Result<ReturnType<typeof options>>) {
             // If one of the changed files is related to the input CSS or JS
             // config/plugin files, then we need to do a full rebuild because
             // the theme might have changed.
-            if (resolvedFullRebuildPaths.includes(file)) {
+            if (resolvedFullRebuildPaths.some((p) => pathsEqual(p, file))) {
               rebuildStrategy = 'full'
 
               // No need to check the rest of the events, because we already know we
diff --git a/packages/@tailwindcss-cli/src/utils/paths-equal.test.ts b/packages/@tailwindcss-cli/src/utils/paths-equal.test.ts
new file mode 100644
index 000000000000..922a1491010b
--- /dev/null
+++ b/packages/@tailwindcss-cli/src/utils/paths-equal.test.ts
@@ -0,0 +1,36 @@
+import { describe, expect, it, vi } from 'vitest'
+
+vi.mock('./paths-equal', async () => {
+  const actual = await vi.importActual<typeof import('./paths-equal')>('./paths-equal')
+  return actual
+})
+
+// We test the logic directly rather than mocking process.platform,
+// because the function captures IS_WINDOWS at module load time.
+// Instead we test the underlying behavior: on the current platform,
+// paths with matching case should always be equal, and we verify
+// the case-insensitive logic separately.
+
+describe('pathsEqual', () => {
+  it('returns true for identical paths', async () => {
+    const { pathsEqual } = await import('./paths-equal')
+    expect(pathsEqual('/foo/bar/baz.css', '/foo/bar/baz.css')).toBe(true)
+  })
+
+  it('returns false for completely different paths', async () => {
+    const { pathsEqual } = await import('./paths-equal')
+    expect(pathsEqual('/foo/bar.css', '/foo/baz.css')).toBe(false)
+  })
+
+  if (process.platform === 'win32') {
+    it('returns true for paths differing only in case on Windows', async () => {
+      const { pathsEqual } = await import('./paths-equal')
+      expect(pathsEqual('C:\\src\\Input.css', 'C:\\src\\input.css')).toBe(true)
+    })
+  } else {
+    it('returns false for paths differing in case on non-Windows', async () => {
+      const { pathsEqual } = await import('./paths-equal')
+      expect(pathsEqual('/src/Input.css', '/src/input.css')).toBe(false)
+    })
+  }
+})
diff --git a/packages/@tailwindcss-cli/src/utils/paths-equal.ts b/packages/@tailwindcss-cli/src/utils/paths-equal.ts
new file mode 100644
index 000000000000..aa56fb887deb
--- /dev/null
+++ b/packages/@tailwindcss-cli/src/utils/paths-equal.ts
@@ -0,0 +1,12 @@
+const IS_WINDOWS = process.platform === 'win32'
+
+/**
+ * Compare two file paths for equality. On Windows, the comparison is
+ * case-insensitive because the filesystem is case-insensitive.
+ */
+export function pathsEqual(a: string, b: string): boolean {
+  if (IS_WINDOWS) {
+    return a.toLowerCase() === b.toLowerCase()
+  }
+  return a === b
+}