diff --git a/integrations/tailwindcss-cli/tests/integration.test.js b/integrations/tailwindcss-cli/tests/integration.test.js
index 72c803782c46..8b8578c80c72 100644
--- a/integrations/tailwindcss-cli/tests/integration.test.js
+++ b/integrations/tailwindcss-cli/tests/integration.test.js
@@ -34,9 +34,9 @@ describe('static build', () => {
       javascript`
         module.exports = {
           content: {
-            content: ['./src/index.html'],
-            safelist: ['bg-red-500','bg-red-600']
+            files: ['./src/index.html'],
           },
+          safelist: ['bg-red-500','bg-red-600'],
           theme: {
             extend: {
             },
diff --git a/integrations/webpack-5/tests/integration.test.js b/integrations/webpack-5/tests/integration.test.js
index b6f654522f9e..58a1c2b191c0 100644
--- a/integrations/webpack-5/tests/integration.test.js
+++ b/integrations/webpack-5/tests/integration.test.js
@@ -230,9 +230,9 @@ describe.each([{ TAILWIND_MODE: 'watch' }, { TAILWIND_MODE: undefined }])('watch
       javascript`
         module.exports = {
           content: {
-            content: ['./src/index.html'],
-            safelist: ['bg-red-500','bg-red-600']
+            files: ['./src/index.html'],
           },
+          safelist: ['bg-red-500','bg-red-600'],
           theme: {
             extend: {
             },
diff --git a/src/cli.js b/src/cli.js
index 2829fd44bd1c..c171dc0a4a35 100644
--- a/src/cli.js
+++ b/src/cli.js
@@ -436,12 +436,8 @@ async function build() {
     return resolvedConfig
   }
 
-  function extractContent(config) {
-    return config.content.files
-  }
-
   function extractFileGlobs(config) {
-    return extractContent(config)
+    return config.content.files
       .filter((file) => {
         // Strings in this case are files / globs. If it is something else,
         // like an object it's probably a raw content object. But this object
@@ -452,7 +448,7 @@ async function build() {
   }
 
   function extractRawContent(config) {
-    return extractContent(config).filter((file) => {
+    return config.content.files.filter((file) => {
       return typeof file === 'object' && file !== null
     })
   }
diff --git a/src/util/normalizeConfig.js b/src/util/normalizeConfig.js
index 11e4d4571483..3a9acb18cb56 100644
--- a/src/util/normalizeConfig.js
+++ b/src/util/normalizeConfig.js
@@ -1,49 +1,126 @@
 import log from './log'
 
-function validate(config, options) {
-  if (!config) return false
-
-  for (let [k, v] of Object.entries(config)) {
-    let types = options[k]
-
-    if (!types) return false
-
-    // Property SHOULD exist, this catches unused keys like `options`
-    if (!types.includes(undefined) && !options.hasOwnProperty(k)) {
-      return false
-    }
-
+export function normalizeConfig(config) {
+  // Quick structure validation
+  /**
+   * type FilePath = string
+   * type RawFile = { raw: string, extension?: string }
+   * type ExtractorFn = (content: string) => Array<string>
+   * type TransformerFn = (content: string) => string
+   *
+   * type Content =
+   *   | Array<FilePath | RawFile>
+   *   | {
+   *       files: Array<FilePath | RawFile>,
+   *       extract?: ExtractorFn | { [extension: string]: ExtractorFn }
+   *       transform?: TransformerFn | { [extension: string]: TransformerFn }
+   *   }
+   */
+  let valid = (() => {
+    // `config.purge` should not exist anymore
+    if (config.purge) return false
+
+    // `config.content` should exist
+    if (!config.content) return false
+
+    // `config.content` should be an object or an array
     if (
-      !types.some((type) => {
-        if (type === undefined) return true
-        return v instanceof type
-      })
+      !Array.isArray(config.content) ||
+      !(typeof config.content === 'object' && config.content !== null)
     ) {
       return false
     }
-  }
 
-  for (let [k, types] of Object.entries(options)) {
-    let value = config[k]
-    if (
-      !types.some((type) => {
-        if (type === undefined) return true
-        return value instanceof type
+    // When `config.content` is an array, it should consist of FilePaths or RawFiles
+    if (Array.isArray(config.content)) {
+      return config.content.every((path) => {
+        // `path` can be a string
+        if (typeof path === 'string') return true
+
+        // `path` can be an object { raw: string, extension?: string }
+        if (
+          // `raw` must be a string
+          typeof path?.raw === 'string' &&
+          // `extension` (if provided) should also be a string
+          path?.extension !== undefined &&
+          typeof path?.extension === 'string'
+        ) {
+          return true
+        }
+
+        return false
       })
-    ) {
-      return false
     }
-  }
 
-  return true
-}
+    // When `config.content` is an object
+    if (typeof config.content === 'object' && config.content !== null) {
+      // Only `files`, `extract` and `transform` can exist in `config.content`
+      if (
+        Object.keys(config.content).some((key) => !['files', 'extract', 'transform'].includes(key))
+      ) {
+        return false
+      }
 
-export function normalizeConfig(config) {
-  // Quick structure validation
-  let valid = validate(config.content, {
-    files: [Array],
-    extract: [undefined, Function, Object],
-  })
+      // `config.content.files` should exist of FilePaths or RawFiles
+      if (Array.isArray(config.content.files)) {
+        if (
+          !config.content.files.every((path) => {
+            // `path` can be a string
+            if (typeof path === 'string') return true
+
+            // `path` can be an object { raw: string, extension?: string }
+            if (
+              // `raw` must be a string
+              typeof path?.raw === 'string' &&
+              // `extension` (if provided) should also be a string
+              path?.extension !== undefined &&
+              typeof path?.extension === 'string'
+            ) {
+              return true
+            }
+
+            return false
+          })
+        ) {
+          return false
+        }
+
+        // `config.content.extract` is optional, and can be a Function or a Record<String, Function>
+        if (typeof config.content.extract === 'object') {
+          for (let value of Object.values(config.content.extract)) {
+            if (typeof value !== 'function') {
+              return false
+            }
+          }
+          return false
+        } else if (
+          !(config.content.extract === undefined || typeof config.content.extract === 'function')
+        ) {
+          return false
+        }
+
+        // `config.content.transform` is optional, and can be a Function or a Record<String, Function>
+        if (typeof config.content.transform === 'object') {
+          for (let value of Object.values(config.content.transform)) {
+            if (typeof value !== 'function') {
+              return false
+            }
+          }
+          return false
+        } else if (
+          !(
+            config.content.transform === undefined || typeof config.content.transform === 'function'
+          )
+        ) {
+          return false
+        }
+      }
+
+      return true
+    }
+
+    return false
+  })()
 
   if (!valid) {
     log.warn('purge-deprecation', [
@@ -86,10 +163,6 @@ export function normalizeConfig(config) {
         if (config.purge?.extract?.DEFAULT) return config.purge.extract.DEFAULT
         if (config.content?.extract?.DEFAULT) return config.content.extract.DEFAULT
 
-        if (config.purge?.options?.defaultExtractor) return config.purge.options.defaultExtractor
-        if (config.content?.options?.defaultExtractor)
-          return config.content.options.defaultExtractor
-
         if (config.purge?.options?.extractors) return config.purge.options.extractors
         if (config.content?.options?.extractors) return config.content.options.extractors
 
@@ -98,6 +171,18 @@ export function normalizeConfig(config) {
 
       let extractors = {}
 
+      extractors.DEFAULT = (() => {
+        if (config.purge?.options?.defaultExtractor) {
+          return config.purge.options.defaultExtractor
+        }
+
+        if (config.content?.options?.defaultExtractor) {
+          return config.content.options.defaultExtractor
+        }
+
+        return undefined
+      })()
+
       // Functions
       if (typeof extract === 'function') {
         extractors.DEFAULT = extract
diff --git a/tests/color-opacity-modifiers.test.js b/tests/color-opacity-modifiers.test.js
index 51da84aacae2..18b0be92bd2d 100644
--- a/tests/color-opacity-modifiers.test.js
+++ b/tests/color-opacity-modifiers.test.js
@@ -62,12 +62,7 @@ test('missing alpha generates nothing', async () => {
 
 test('arbitrary color with opacity from scale', async () => {
   let config = {
-    mode: 'jit',
-    purge: [
-      {
-        raw: 'bg-[wheat]/50',
-      },
-    ],
+    content: [{ raw: 'bg-[wheat]/50' }],
     theme: {},
     plugins: [],
   }
@@ -85,12 +80,7 @@ test('arbitrary color with opacity from scale', async () => {
 
 test('arbitrary color with arbitrary opacity', async () => {
   let config = {
-    mode: 'jit',
-    purge: [
-      {
-        raw: 'bg-[#bada55]/[0.2]',
-      },
-    ],
+    content: [{ raw: 'bg-[#bada55]/[0.2]' }],
     theme: {},
     plugins: [],
   }
@@ -108,12 +98,7 @@ test('arbitrary color with arbitrary opacity', async () => {
 
 test('undefined theme color with opacity from scale', async () => {
   let config = {
-    mode: 'jit',
-    purge: [
-      {
-        raw: 'bg-garbage/50',
-      },
-    ],
+    content: [{ raw: 'bg-garbage/50' }],
     theme: {},
     plugins: [],
   }
diff --git a/tests/custom-extractors.test.js b/tests/custom-extractors.test.js
index 9ce08dcb254f..9a8301230a0b 100644
--- a/tests/custom-extractors.test.js
+++ b/tests/custom-extractors.test.js
@@ -41,13 +41,26 @@ describe('modern', () => {
       expect(result.css).toMatchFormattedCss(expected)
     })
   })
+
+  test('extract function', () => {
+    let config = {
+      content: {
+        files: [path.resolve(__dirname, './custom-extractors.test.html')],
+        extract: customExtractor,
+      },
+    }
+
+    return run('@tailwind utilities', config).then((result) => {
+      expect(result.css).toMatchFormattedCss(expected)
+    })
+  })
 })
 
 describe('legacy', () => {
   test('defaultExtractor', () => {
     let config = {
       content: {
-        content: [path.resolve(__dirname, './custom-extractors.test.html')],
+        files: [path.resolve(__dirname, './custom-extractors.test.html')],
         options: {
           defaultExtractor: customExtractor,
         },
@@ -62,7 +75,7 @@ describe('legacy', () => {
   test('extractors array', () => {
     let config = {
       content: {
-        content: [path.resolve(__dirname, './custom-extractors.test.html')],
+        files: [path.resolve(__dirname, './custom-extractors.test.html')],
         options: {
           extractors: [
             {
@@ -78,17 +91,4 @@ describe('legacy', () => {
       expect(result.css).toMatchFormattedCss(expected)
     })
   })
-
-  test('extract function', () => {
-    let config = {
-      content: {
-        content: [path.resolve(__dirname, './custom-extractors.test.html')],
-        extract: customExtractor,
-      },
-    }
-
-    return run('@tailwind utilities', config).then((result) => {
-      expect(result.css).toMatchFormattedCss(expected)
-    })
-  })
 })
diff --git a/tests/custom-transformers.test.js b/tests/custom-transformers.test.js
index 9402dd3007a7..bfee9c8e5266 100644
--- a/tests/custom-transformers.test.js
+++ b/tests/custom-transformers.test.js
@@ -7,7 +7,7 @@ function customTransformer(content) {
 test('transform function', () => {
   let config = {
     content: {
-      content: [{ raw: html`<div class="uppercase"></div>` }],
+      files: [{ raw: html`<div class="uppercase"></div>` }],
       transform: customTransformer,
     },
   }
@@ -24,7 +24,7 @@ test('transform function', () => {
 test('transform.DEFAULT', () => {
   let config = {
     content: {
-      content: [{ raw: html`<div class="uppercase"></div>` }],
+      files: [{ raw: html`<div class="uppercase"></div>` }],
       transform: {
         DEFAULT: customTransformer,
       },
@@ -43,7 +43,7 @@ test('transform.DEFAULT', () => {
 test('transform.{extension}', () => {
   let config = {
     content: {
-      content: [
+      files: [
         { raw: html`<div class="uppercase"></div>`, extension: 'html' },
         { raw: html`<div class="uppercase"></div>`, extension: 'php' },
       ],
diff --git a/tests/normalize-config.test.js b/tests/normalize-config.test.js
index 4ead50794476..602e10963a6c 100644
--- a/tests/normalize-config.test.js
+++ b/tests/normalize-config.test.js
@@ -46,3 +46,52 @@ it.each`
     `)
   })
 })
+
+it('should still be possible to use the "old" v2 config', () => {
+  let config = {
+    purge: {
+      content: [
+        { raw: 'text-svelte', extension: 'svelte' },
+        { raw: '# My Big Heading', extension: 'md' },
+      ],
+      options: {
+        defaultExtractor(content) {
+          return content.split(' ').concat(['font-bold'])
+        },
+      },
+      extract: {
+        svelte(content) {
+          return content.replace('svelte', 'center').split(' ')
+        },
+      },
+      transform: {
+        md() {
+          return 'text-4xl'
+        },
+      },
+    },
+    theme: {
+      extends: {},
+    },
+    variants: {
+      extends: {},
+    },
+  }
+
+  return run('@tailwind utilities', config).then((result) => {
+    return expect(result.css).toMatchFormattedCss(css`
+      .text-center {
+        text-align: center;
+      }
+
+      .text-4xl {
+        font-size: 2.25rem;
+        line-height: 2.5rem;
+      }
+
+      .font-bold {
+        font-weight: 700;
+      }
+    `)
+  })
+})
diff --git a/tests/raw-content.test.js b/tests/raw-content.test.js
index 563d2b50cb3e..c24dba919ecd 100644
--- a/tests/raw-content.test.js
+++ b/tests/raw-content.test.js
@@ -29,19 +29,14 @@ test('raw content with extension', () => {
   let tailwind = require('../src')
   let config = {
     content: {
-      content: [
+      files: [
         {
           raw: fs.readFileSync(path.resolve(__dirname, './raw-content.test.html'), 'utf8'),
           extension: 'html',
         },
       ],
-      options: {
-        extractors: [
-          {
-            extractor: () => ['invisible'],
-            extensions: ['html'],
-          },
-        ],
+      extract: {
+        html: () => ['invisible'],
       },
     },
     corePlugins: { preflight: false },
diff --git a/tests/resolveConfig.test.js b/tests/resolveConfig.test.js
index dba44d32e137..d8d0d8c3d363 100644
--- a/tests/resolveConfig.test.js
+++ b/tests/resolveConfig.test.js
@@ -10,6 +10,7 @@ test('prefix key overrides default prefix', () => {
     prefix: '',
     important: false,
     separator: ':',
+    content: [],
     theme: {
       screens: {
         mobile: '400px',
@@ -40,6 +41,7 @@ test('important key overrides default important', () => {
     prefix: '',
     important: false,
     separator: ':',
+    content: [],
     theme: {
       screens: {
         mobile: '400px',
@@ -70,6 +72,7 @@ test('important (selector) key overrides default important', () => {
     prefix: '',
     important: false,
     separator: ':',
+    content: [],
     theme: {
       screens: {
         mobile: '400px',
@@ -100,6 +103,7 @@ test('separator key overrides default separator', () => {
     prefix: '',
     important: false,
     separator: ':',
+    content: [],
     theme: {
       screens: {
         mobile: '400px',
@@ -134,6 +138,7 @@ test('theme key is merged instead of replaced', () => {
     prefix: '-',
     important: false,
     separator: ':',
+    content: [],
     theme: {
       colors: {
         'grey-darker': '#606f7b',
@@ -197,6 +202,7 @@ test('theme key is deeply merged instead of replaced', () => {
     prefix: '-',
     important: false,
     separator: ':',
+    content: [],
     theme: {
       colors: {
         grey: {
@@ -235,6 +241,7 @@ test('missing top level keys are pulled from the default config', () => {
     prefix: '-',
     important: false,
     separator: ':',
+    content: [],
     theme: {
       colors: { green: '#00ff00' },
       screens: {
@@ -273,6 +280,7 @@ test('functions in the default theme section are lazily evaluated', () => {
     prefix: '-',
     important: false,
     separator: ':',
+    content: [],
     theme: {
       colors: {
         cyan: 'cyan',
@@ -333,6 +341,7 @@ test('functions in the user theme section are lazily evaluated', () => {
     prefix: '-',
     important: false,
     separator: ':',
+    content: [],
     theme: {
       colors: {
         cyan: 'cyan',
@@ -391,6 +400,7 @@ test('theme values in the extend section extend the existing theme', () => {
     prefix: '-',
     important: false,
     separator: ':',
+    content: [],
     theme: {
       colors: {
         cyan: 'cyan',
@@ -461,6 +471,7 @@ test('theme values in the extend section extend the user theme', () => {
     prefix: '-',
     important: false,
     separator: ':',
+    content: [],
     theme: {
       opacity: {
         0: '0',
@@ -535,6 +546,7 @@ test('theme values in the extend section can extend values that are depended on
     prefix: '-',
     important: false,
     separator: ':',
+    content: [],
     theme: {
       colors: {
         cyan: 'cyan',
@@ -588,6 +600,7 @@ test('theme values in the extend section are not deeply merged when they are sim
     prefix: '-',
     important: false,
     separator: ':',
+    content: [],
     theme: {
       fonts: {
         sans: ['system-ui', 'Helvetica Neue', 'sans-serif'],
@@ -636,6 +649,7 @@ test('theme values in the extend section are deeply merged, when they are arrays
     prefix: '-',
     important: false,
     separator: ':',
+    content: [],
     theme: {
       typography: {
         ArrayArray: {
@@ -696,6 +710,7 @@ test('the theme function can use a default value if the key is missing', () => {
     prefix: '-',
     important: false,
     separator: ':',
+    content: [],
     theme: {
       colors: {
         cyan: 'cyan',
@@ -750,6 +765,7 @@ test('the theme function can resolve function values', () => {
     prefix: '-',
     important: false,
     separator: ':',
+    content: [],
     theme: {
       colors: {
         red: 'red',
@@ -808,6 +824,7 @@ test('the theme function can resolve deep function values', () => {
     prefix: '-',
     important: false,
     separator: ':',
+    content: [],
     theme: {
       spacing: {
         0: '0',
@@ -864,6 +881,7 @@ test('theme values in the extend section are lazily evaluated', () => {
     prefix: '-',
     important: false,
     separator: ':',
+    content: [],
     theme: {
       colors: {
         cyan: 'cyan',
@@ -924,6 +942,7 @@ test('lazily evaluated values have access to the config utils', () => {
     prefix: '-',
     important: false,
     separator: ':',
+    content: [],
     theme: {
       spacing: {
         1: '1px',
@@ -1010,6 +1029,7 @@ test('the original theme is not mutated', () => {
     prefix: '-',
     important: false,
     separator: ':',
+    content: [],
     theme: {
       colors: {
         cyan: 'cyan',
@@ -1058,6 +1078,7 @@ test('custom properties are multiplied by -1 for negative values', () => {
     prefix: '-',
     important: false,
     separator: ':',
+    content: [],
     theme: {},
   }
 
@@ -1165,6 +1186,7 @@ test('more than two config objects can be resolved', () => {
     prefix: '-',
     important: false,
     separator: ':',
+    content: [],
     theme: {
       fontFamily: {
         body: ['Arial', 'sans-serif'],
@@ -1233,6 +1255,7 @@ test('plugin config modifications are applied', () => {
     prefix: '',
     important: false,
     separator: ':',
+    content: [],
     theme: {
       screens: {
         mobile: '400px',
@@ -1271,6 +1294,7 @@ test('user config takes precedence over plugin config modifications', () => {
     prefix: '',
     important: false,
     separator: ':',
+    content: [],
     theme: {
       screens: {
         mobile: '400px',
@@ -1321,6 +1345,7 @@ test('plugin config can register plugins that also have config', () => {
     prefix: '',
     important: false,
     separator: ':',
+    content: [],
     theme: {
       screens: {
         mobile: '400px',
@@ -1366,6 +1391,7 @@ test('plugin configs take precedence over plugin configs registered by that plug
     prefix: '',
     important: false,
     separator: ':',
+    content: [],
     theme: {
       screens: {
         mobile: '400px',
@@ -1416,6 +1442,7 @@ test('plugin theme extensions are added even if user overrides top-level theme c
     prefix: '',
     important: false,
     separator: ':',
+    content: [],
     theme: {
       width: {
         sm: '1rem',
@@ -1477,6 +1504,7 @@ test('user theme extensions take precedence over plugin theme extensions with th
     prefix: '',
     important: false,
     separator: ':',
+    content: [],
     theme: {
       width: {
         sm: '1rem',
@@ -1549,6 +1577,7 @@ test('extensions are applied in the right order', () => {
   }
 
   const defaultConfig = {
+    content: [],
     theme: {
       colors: {
         grey: {
@@ -1583,6 +1612,7 @@ test('core plugin configuration builds on the default list when starting with an
     prefix: '',
     important: false,
     separator: ':',
+    content: [],
     theme: {},
     corePlugins: {},
   }
@@ -1608,6 +1638,7 @@ test('core plugins that are disabled by default can be enabled', () => {
     prefix: '',
     important: false,
     separator: ':',
+    content: [],
     theme: {},
     corePlugins: { display: false },
   }
@@ -1631,6 +1662,7 @@ test('core plugin configurations stack', () => {
     prefix: '',
     important: false,
     separator: ':',
+    content: [],
     theme: {},
     corePlugins: ['float', 'display', 'padding'],
   }
@@ -1660,6 +1692,7 @@ test('plugins are merged', () => {
     prefix: '',
     important: false,
     separator: ':',
+    content: [],
     theme: {},
   }
 
@@ -1691,6 +1724,7 @@ test('all helpers can be destructured from the first function argument', () => {
     prefix: '-',
     important: false,
     separator: ':',
+    content: [],
     theme: {
       screens: {
         sm: '640px',