diff --git a/CHANGELOG.md b/CHANGELOG.md
index d8d05d228..8c6bf3eb1 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -21,6 +21,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 - Evaluate theme functions in plugins and JS config files ([#14326](https://github.com/tailwindlabs/tailwindcss/pull/14326))
 - Ensure theme values overridden with `reference` values don't generate stale CSS variables ([#14327](https://github.com/tailwindlabs/tailwindcss/pull/14327))
 - Don’t suggest named opacity modifiers in intellisense ([#14339](https://github.com/tailwindlabs/tailwindcss/pull/14339))
+- Fix a crash with older Node.js versions ([#14342](https://github.com/tailwindlabs/tailwindcss/pull/14342))
 
 ## [4.0.0-alpha.21] - 2024-09-02
 
diff --git a/packages/@tailwindcss-node/src/index.cts b/packages/@tailwindcss-node/src/index.cts
index bb1fabe85..a143865ef 100644
--- a/packages/@tailwindcss-node/src/index.cts
+++ b/packages/@tailwindcss-node/src/index.cts
@@ -5,5 +5,9 @@ export * from './compile'
 // In Bun, ESM modules will also populate `require.cache`, so the module hook is
 // not necessary.
 if (!process.versions.bun) {
-  Module.register(pathToFileURL(require.resolve('@tailwindcss/node/esm-cache-loader')))
+  // `Module#register` was added in Node v18.19.0 and v20.6.0
+  //
+  // Not calling it means that while ESM dependencies don't get reloaded, the
+  // actual included files will because they cache bust directly via `?id=…`
+  Module.register?.(pathToFileURL(require.resolve('@tailwindcss/node/esm-cache-loader')))
 }
diff --git a/packages/@tailwindcss-node/src/index.ts b/packages/@tailwindcss-node/src/index.ts
index 2fcbfa89b..85b292ed0 100644
--- a/packages/@tailwindcss-node/src/index.ts
+++ b/packages/@tailwindcss-node/src/index.ts
@@ -6,5 +6,10 @@ export * from './compile'
 // not necessary.
 if (!process.versions.bun) {
   let localRequire = Module.createRequire(import.meta.url)
-  Module.register(pathToFileURL(localRequire.resolve('@tailwindcss/node/esm-cache-loader')))
+
+  // `Module#register` was added in Node v18.19.0 and v20.6.0
+  //
+  // Not calling it means that while ESM dependencies don't get reloaded, the
+  // actual included files will because they cache bust directly via `?id=…`
+  Module.register?.(pathToFileURL(localRequire.resolve('@tailwindcss/node/esm-cache-loader')))
 }