diff --git a/examples/webpack-plugin/WebpackPlugin.js b/examples/webpack-plugin/WebpackPlugin.js
deleted file mode 100644
index 84a9a9d6f8..0000000000
--- a/examples/webpack-plugin/WebpackPlugin.js
+++ /dev/null
@@ -1,17 +0,0 @@
-/**
- * Just a normal Webpack plugin
- */
-export class WebpackPlugin {
-  constructor(log) {
-    this.log = log
-  }
-
-  apply(compiler) {
-    if (!this.log) return
-
-    this.log({
-      message: this.constructor.name,
-      suffix: 'applied!',
-    })
-  }
-}
diff --git a/examples/webpack-plugin/WebpackPlugin.ts b/examples/webpack-plugin/WebpackPlugin.ts
new file mode 100644
index 0000000000..bbfe25dedb
--- /dev/null
+++ b/examples/webpack-plugin/WebpackPlugin.ts
@@ -0,0 +1,11 @@
+/**
+ * Just a normal Webpack plugin
+ */
+export class WebpackPlugin {
+  constructor(public log: (...args: any[]) => void) {
+  }
+
+  apply(compiler: any) {
+    this.log?.(this.constructor.name, 'applied!')
+  }
+}
diff --git a/examples/webpack-plugin/bud.config.ts b/examples/webpack-plugin/bud.config.ts
index 1e9cf3d1e8..540604b122 100644
--- a/examples/webpack-plugin/bud.config.ts
+++ b/examples/webpack-plugin/bud.config.ts
@@ -1,6 +1,6 @@
 import {bud} from '@roots/bud'
 
-import {WebpackPlugin} from './WebpackPlugin.js'
+const {WebpackPlugin} = require('./WebpackPlugin.js')
 
 /**
  * This is an example of how to use a Webpack plugin
@@ -20,7 +20,7 @@ bud
   .use({
     label: `inline-plugin`,
     apply: async () => {
-      console.log({message: 'inline-plugin', suffix: 'applied!'})
+      console.log('inline-plugin applied!')
       await bud.fs.write(
         bud.path(`@storage`, `inline-plugin-output`),
         `inline-plugin-test-success`,
@@ -35,13 +35,13 @@ bud
     {
       label: `array-plugin-1`,
       apply() {
-        console.log({message: 'array-plugin-1', suffix: 'applied!'})
+        console.log('array-plugin-1 applied!')
       },
     },
     new (class {
       public label = `array-plugin-2`
       public apply() {
-        console.log({message: 'array-plugin-2', suffix: 'applied!'})
+        console.log('array-plugin-2 applied!')
       }
     })(),
   ])
diff --git a/sources/@roots/bud-support/package.json b/sources/@roots/bud-support/package.json
index 2f09aef5ac..8b36befc32 100644
--- a/sources/@roots/bud-support/package.json
+++ b/sources/@roots/bud-support/package.json
@@ -55,6 +55,7 @@
     "./axios": "./lib/axios/index.js",
     "./chalk": "./lib/chalk/index.js",
     "./chokidar": "./lib/chokidar/index.js",
+    "./cjs-shim": "./lib/cjs-shim/index.js",
     "./clean-stack": "./lib/clean-stack/index.js",
     "./clean-webpack-plugin": "./lib/clean-webpack-plugin/index.js",
     "./clipanion": "./lib/clipanion/index.js",
@@ -132,6 +133,9 @@
       "chokidar": [
         "./lib/chokidar/index.d.ts"
       ],
+      "cjs-shim": [
+        "./lib/cjs-shim/index.d.ts"
+      ],
       "clean-stack": [
         "./lib/clean-stack/index.d.ts"
       ],
diff --git a/sources/@roots/bud-support/src/cjs-shim/index.ts b/sources/@roots/bud-support/src/cjs-shim/index.ts
new file mode 100644
index 0000000000..9ec48442e7
--- /dev/null
+++ b/sources/@roots/bud-support/src/cjs-shim/index.ts
@@ -0,0 +1,7 @@
+import {createRequire} from 'node:module'
+import path from 'node:path'
+import url from 'node:url'
+
+globalThis.require = createRequire(import.meta.url)
+globalThis.__filename = url.fileURLToPath(import.meta.url)
+globalThis.__dirname = path.dirname(__filename)
diff --git a/sources/@roots/bud-support/src/utilities/files.ts b/sources/@roots/bud-support/src/utilities/files.ts
index 44bbbef3b9..19c1e3eaae 100644
--- a/sources/@roots/bud-support/src/utilities/files.ts
+++ b/sources/@roots/bud-support/src/utilities/files.ts
@@ -2,6 +2,7 @@ import type * as esbuild from '@roots/bud-support/esbuild'
 import type {Filesystem} from '@roots/bud-support/filesystem'
 import type {InspectResult} from '@roots/filesystem/filesystem'
 
+import {builtinModules} from 'node:module'
 import {join, parse} from 'node:path'
 
 import * as filesystem from '@roots/bud-support/filesystem'
@@ -163,17 +164,16 @@ async function getFileInfo(filename: string) {
         paths.storage,
         `configs`,
         file.base,
-        `${current.sha1}${file.ext.replace(/(.*)ts$/, `$1js`)}`,
+        `${current.sha1}${file.ext.replace(/(.*)ts$/, `$1mjs`)}`,
       )
 
       const modified = current.sha1 !== file.sha1
       const uncompiled = !(await fs.exists(outfile))
 
       if (modified || uncompiled) {
-        if (uncompiled)
-          logger.log(`${file.name} has not been compiled yet`)
-        else if (modified)
-          logger.log(`${file.name} has been modified since last compiled`)
+        uncompiled && logger.log(file.name, `has not been compiled yet`)
+        modified &&
+          logger.log(file.name, `has been modified since last compiled`)
 
         // Update the hash to the current state
         file.sha1 = current.sha1
@@ -186,7 +186,7 @@ async function getFileInfo(filename: string) {
       const tmpfile = join(
         paths.basedir,
         file.dir,
-        `.${file.name}${file.ext.replace(/(.*)ts$/, `$1js`)}`,
+        `.${file.name}${file.ext.replace(/(.*)ts$/, `$1mjs`)}`,
       )
 
       logger.scope(`fs`).info(`copying ${outfile} to tmpfile:`, tmpfile)
@@ -232,7 +232,11 @@ async function esTransform({
   await transformer.build({
     absWorkingDir: paths.basedir,
     allowOverwrite: true,
+    bundle: true,
     entryPoints: [file.path],
+    external: [`@roots/bud`, `node:*`, ...builtinModules],
+    format: `esm`,
+    inject: [`@roots/bud-support/cjs-shim`],
     outfile,
     platform: `node`,
   })
@@ -252,8 +256,10 @@ function getFileType(
 function getFileTarget(file: {name?: string}) {
   if (file.name?.includes(`production`) || file.name?.includes(`prod`))
     return `production`
+
   if (file.name?.includes(`development`) || file.name?.includes(`dev`))
     return `development`
+
   return `base`
 }
 
diff --git a/sources/@roots/bud-tailwindcss/src/extension/index.ts b/sources/@roots/bud-tailwindcss/src/extension/index.ts
index 3f75216b89..4510d6ee9e 100644
--- a/sources/@roots/bud-tailwindcss/src/extension/index.ts
+++ b/sources/@roots/bud-tailwindcss/src/extension/index.ts
@@ -44,7 +44,6 @@ class BudTailwindCss extends BudTailwindOptionsApi {
       )
       .setPlugin(`tailwindcss`, [
         await this.resolve(`tailwindcss`, import.meta.url),
-        this.configPath ?? this.config,
       ])
       .setPluginOptions(`env`, {
         features: {
@@ -70,18 +69,19 @@ class BudTailwindCss extends BudTailwindOptionsApi {
     })
   }
 
+  /**
+   * {@link Extension.configAfter}
+   */
   @bind
   public override async configAfter(bud: Bud) {
-    this.setResolvedConfig(this.resolveConfig())
-    const options = this.configPath ?? (this.config as any)
-    bud.postcss.setPluginOptions(`tailwindcss`, options)
+    bud.postcss.setPluginOptions(`tailwindcss`, this.resolveConfig())
   }
 
   /**
    * {@link Extension.register}
    */
   @bind
-  public override async register(_bud: Bud) {
+  public override async register() {
     await this.sourceConfig()
   }
 }
diff --git a/sources/@roots/bud-tailwindcss/src/extension/options.ts b/sources/@roots/bud-tailwindcss/src/extension/options.ts
index 4653d42dc1..5639be0e46 100644
--- a/sources/@roots/bud-tailwindcss/src/extension/options.ts
+++ b/sources/@roots/bud-tailwindcss/src/extension/options.ts
@@ -94,6 +94,7 @@ class BudTailwindOptionsApi
   >(...params: [K, VK] | [V]) {
     if (params.length === 1) {
       const [value] = params
+
       this.setConfig((config = {content: []}) => ({
         ...config,
         theme: {
@@ -101,7 +102,7 @@ class BudTailwindOptionsApi
           extend: {...(config?.theme?.extend ?? {}), ...value},
         },
       }))
-      this.resolveConfig()
+
       return this
     }
 
@@ -114,8 +115,6 @@ class BudTailwindOptionsApi
       },
     }))
 
-    this.resolveConfig()
-
     return this
   }
 
@@ -140,17 +139,23 @@ class BudTailwindOptionsApi
    */
   @bind
   public generateImports(
-    imports: Array<`${keyof ThemeConfig & string}`> | boolean = true,
+    imports:
+      | Array<
+          | `${keyof ThemeConfig & string}.${string}`
+          | `${keyof ThemeConfig & string}`
+        >
+      | boolean = true,
   ) {
-    this.resolveConfig()
-
     const makeStaticModule = (key: `${keyof ThemeConfig & string}`) => {
+      this.logger.log(`@tailwind/${key}`, `generating module`)
+
       const value = get(this.resolvedConfig.theme, key)
-      this.logger.log(`@tailwind/${key}: generating module`)
       return `export default ${JSON.stringify(value)};`
     }
 
     this.app.hooks.action(`config.after`, async bud => {
+      this.resolveConfig()
+
       const importableKeys = Array.isArray(imports)
         ? imports
         : Object.keys(this.resolvedConfig.theme)
@@ -209,10 +214,11 @@ class BudTailwindOptionsApi
    * Resolve a tailwind config value
    */
   @bind
-  public resolveThemeValue<K extends `${keyof ThemeConfig & string}`>(
-    key: K,
-    extendedOnly?: boolean,
-  ): Config[K] {
+  public resolveThemeValue<
+    K extends
+      | `${keyof ThemeConfig & string}.${string}`
+      | `${keyof ThemeConfig & string}`,
+  >(key: K, extendedOnly?: boolean): Config[K] {
     if (extendedOnly) {
       if (!this.config?.theme?.extend)
         throw new Error(
@@ -229,7 +235,8 @@ class BudTailwindOptionsApi
       return isFunction(value) ? value(pluginUtils) : value
     }
 
-    const value = this.resolvedConfig?.theme?.[key]
+    const value = get(this.resolveConfig()?.theme, key)
+
     if (!value) {
       throw new Error(
         `@roots/bud-tailwindcss: ${key} is not a valid tailwind theme key.`,
@@ -251,7 +258,6 @@ class BudTailwindOptionsApi
       ...config,
       plugins,
     }))
-    this.resolveConfig()
     return this
   }
 
@@ -271,7 +277,6 @@ class BudTailwindOptionsApi
         ...config,
         theme: {...(config.theme ?? {}), ...value},
       }))
-      this.resolveConfig()
       return this
     }
 
@@ -280,7 +285,6 @@ class BudTailwindOptionsApi
       ...config,
       theme: {...(config.theme ?? {}), [key]: value},
     }))
-    this.resolveConfig()
     return this
   }
 
diff --git a/tests/integration/webpack-plugin.test.ts b/tests/integration/webpack-plugin.test.ts
index d2767cdf83..445f5db46a 100644
--- a/tests/integration/webpack-plugin.test.ts
+++ b/tests/integration/webpack-plugin.test.ts
@@ -40,9 +40,10 @@ describe(`examples/webpack-plugin`, () => {
     ).toEqual(`inline-plugin-test-success`)
 
     expect(await fs.read(test.getPath(`build.stdout.log`)))
-      .toMatch(`{ message: 'WebpackPlugin', suffix: 'applied!' }
-{ message: 'inline-plugin', suffix: 'applied!' }
-{ message: 'array-plugin-1', suffix: 'applied!' }
-{ message: 'array-plugin-2', suffix: 'applied!' }`)
+      .toMatch(`\
+WebpackPlugin applied!
+inline-plugin applied!
+array-plugin-1 applied!
+array-plugin-2 applied!`)
   })
 })