diff --git a/.github/workflows/integration-tests.yml b/.github/workflows/integration-tests.yml
index 4c2812b6196a..9d813ad5bed8 100644
--- a/.github/workflows/integration-tests.yml
+++ b/.github/workflows/integration-tests.yml
@@ -15,7 +15,16 @@ jobs:
 
     strategy:
       matrix:
-        integration: [parcel, postcss-cli, rollup, rollup-sass, tailwindcss-cli, vite, webpack-4, webpack-5]
+        integration:
+          - content-resolution
+          - parcel
+          - postcss-cli
+          - rollup
+          - rollup-sass
+          - tailwindcss-cli
+          - vite
+          - webpack-4
+          - webpack-5
         node-version: [16]
 
     steps:
diff --git a/CHANGELOG.md b/CHANGELOG.md
index 22209b0ec786..9a11b1ee15f1 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -15,6 +15,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 - Add negative value support for `outline-offset` ([#9136](https://github.com/tailwindlabs/tailwindcss/pull/9136))
 - Allow negating utilities using min/max/clamp ([#9237](https://github.com/tailwindlabs/tailwindcss/pull/9237))
 - Add new `collapse` utility for `visibility: collapse` ([#9181](https://github.com/tailwindlabs/tailwindcss/pull/9181))
+- Allow resolving content paths relative to the config file ([#9396](https://github.com/tailwindlabs/tailwindcss/pull/9396))
 
 ### Fixed
 
diff --git a/integrations/content-resolution/.gitignore b/integrations/content-resolution/.gitignore
new file mode 100644
index 000000000000..3c0e7734cfb3
--- /dev/null
+++ b/integrations/content-resolution/.gitignore
@@ -0,0 +1 @@
+*.tailwind.config.js
diff --git a/integrations/content-resolution/package-lock.json b/integrations/content-resolution/package-lock.json
new file mode 100644
index 000000000000..8f720899b1e7
--- /dev/null
+++ b/integrations/content-resolution/package-lock.json
@@ -0,0 +1,1369 @@
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+      "integrity": "sha512-U9nH88a3fc/ekCF1l0/UP1IosiuIjyTh7hBvXVMHYgVcfGvt897Xguj2UOLDeI5BG2m7/uwyaLVT6fbtCwTyzw==",
+      "dev": true
+    },
+    "run-parallel": {
+      "version": "1.2.0",
+      "resolved": "https://registry.npmjs.org/run-parallel/-/run-parallel-1.2.0.tgz",
+      "integrity": "sha512-5l4VyZR86LZ/lDxZTR6jqL8AFE2S0IFLMP26AbjsLVADxHdhB/c0GUsH+y39UfCi3dzz8OlQuPmnaJOMoDHQBA==",
+      "dev": true,
+      "requires": {
+        "queue-microtask": "^1.2.2"
+      }
+    },
+    "slash": {
+      "version": "4.0.0",
+      "resolved": "https://registry.npmjs.org/slash/-/slash-4.0.0.tgz",
+      "integrity": "sha512-3dOsAHXXUkQTpOYcoAxLIorMTp4gIQr5IW3iVb7A7lFIp0VHhnynm9izx6TssdrIcVIESAlVjtnO2K8bg+Coew==",
+      "dev": true
+    },
+    "source-map-js": {
+      "version": "1.0.2",
+      "resolved": "https://registry.npmjs.org/source-map-js/-/source-map-js-1.0.2.tgz",
+      "integrity": "sha512-R0XvVJ9WusLiqTCEiGCmICCMplcCkIwwR11mOSD9CR5u+IXYdiseeEuXCVAjS54zqwkLcPNnmU4OeJ6tUrWhDw==",
+      "dev": true
+    },
+    "string-width": {
+      "version": "4.2.3",
+      "resolved": "https://registry.npmjs.org/string-width/-/string-width-4.2.3.tgz",
+      "integrity": "sha512-wKyQRQpjJ0sIp62ErSZdGsjMJWsap5oRNihHhu6G7JVO/9jIB6UyevL+tXuOqrng8j/cxKTWyWUwvSTriiZz/g==",
+      "dev": true,
+      "requires": {
+        "emoji-regex": "^8.0.0",
+        "is-fullwidth-code-point": "^3.0.0",
+        "strip-ansi": "^6.0.1"
+      }
+    },
+    "strip-ansi": {
+      "version": "6.0.1",
+      "resolved": "https://registry.npmjs.org/strip-ansi/-/strip-ansi-6.0.1.tgz",
+      "integrity": "sha512-Y38VPSHcqkFrCpFnQ9vuSXmquuv5oXOKpGeT6aGrr3o3Gc9AlVa6JBfUSOCnbxGGZF+/0ooI7KrPuUSztUdU5A==",
+      "dev": true,
+      "requires": {
+        "ansi-regex": "^5.0.1"
+      }
+    },
+    "thenby": {
+      "version": "1.3.4",
+      "resolved": "https://registry.npmjs.org/thenby/-/thenby-1.3.4.tgz",
+      "integrity": "sha512-89Gi5raiWA3QZ4b2ePcEwswC3me9JIg+ToSgtE0JWeCynLnLxNr/f9G+xfo9K+Oj4AFdom8YNJjibIARTJmapQ==",
+      "dev": true
+    },
+    "to-regex-range": {
+      "version": "5.0.1",
+      "resolved": "https://registry.npmjs.org/to-regex-range/-/to-regex-range-5.0.1.tgz",
+      "integrity": "sha512-65P7iz6X5yEr1cwcgvQxbbIw7Uk3gOy5dIdtZ4rDveLqhrdJP+Li/Hx6tyK0NEb+2GCyneCMJiGqrADCSNk8sQ==",
+      "dev": true,
+      "requires": {
+        "is-number": "^7.0.0"
+      }
+    },
+    "universalify": {
+      "version": "2.0.0",
+      "resolved": "https://registry.npmjs.org/universalify/-/universalify-2.0.0.tgz",
+      "integrity": "sha512-hAZsKq7Yy11Zu1DE0OzWjw7nnLZmJZYTDZZyEFHZdUhV8FkH5MCfoU1XMaxXovpyW5nq5scPqq0ZDP9Zyl04oQ==",
+      "dev": true
+    },
+    "wrap-ansi": {
+      "version": "7.0.0",
+      "resolved": "https://registry.npmjs.org/wrap-ansi/-/wrap-ansi-7.0.0.tgz",
+      "integrity": "sha512-YVGIj2kamLSTxw6NsZjoBxfSwsn0ycdesmc4p+Q21c5zPuZ1pl+NfxVdxPtdHvmNVOQ6XSYG4AUtyt/Fi7D16Q==",
+      "dev": true,
+      "requires": {
+        "ansi-styles": "^4.0.0",
+        "string-width": "^4.1.0",
+        "strip-ansi": "^6.0.0"
+      }
+    },
+    "y18n": {
+      "version": "5.0.8",
+      "resolved": "https://registry.npmjs.org/y18n/-/y18n-5.0.8.tgz",
+      "integrity": "sha512-0pfFzegeDWJHJIAmTLRP2DwHjdF5s7jo9tuztdQxAhINCdvS+3nGINqPd00AphqJR/0LhANUS6/+7SCb98YOfA==",
+      "dev": true
+    },
+    "yaml": {
+      "version": "1.10.2",
+      "resolved": "https://registry.npmjs.org/yaml/-/yaml-1.10.2.tgz",
+      "integrity": "sha512-r3vXyErRCYJ7wg28yvBY5VSoAF8ZvlcW9/BwUzEtUsjvX/DKs24dIkuwjtuprwJJHsbyUbLApepYTR1BN4uHrg==",
+      "dev": true
+    },
+    "yargs": {
+      "version": "17.5.1",
+      "resolved": "https://registry.npmjs.org/yargs/-/yargs-17.5.1.tgz",
+      "integrity": "sha512-t6YAJcxDkNX7NFYiVtKvWUz8l+PaKTLiL63mJYWR2GnHq2gjEWISzsLp9wg3aY36dY1j+gfIEL3pIF+XlJJfbA==",
+      "dev": true,
+      "requires": {
+        "cliui": "^7.0.2",
+        "escalade": "^3.1.1",
+        "get-caller-file": "^2.0.5",
+        "require-directory": "^2.1.1",
+        "string-width": "^4.2.3",
+        "y18n": "^5.0.5",
+        "yargs-parser": "^21.0.0"
+      }
+    },
+    "yargs-parser": {
+      "version": "21.1.1",
+      "resolved": "https://registry.npmjs.org/yargs-parser/-/yargs-parser-21.1.1.tgz",
+      "integrity": "sha512-tVpsJW7DdjecAiFpbIB1e3qxIQsE6NoPc5/eTdrbbIC4h0LVsWhnoa3g+m2HclBIujHzsxZ4VJVA+GUuc2/LBw==",
+      "dev": true
+    }
+  }
+}
diff --git a/integrations/content-resolution/package.json b/integrations/content-resolution/package.json
new file mode 100644
index 000000000000..32923b2fcccf
--- /dev/null
+++ b/integrations/content-resolution/package.json
@@ -0,0 +1,20 @@
+{
+  "name": "postcss-cli",
+  "private": true,
+  "version": "0.0.0",
+  "scripts": {
+    "build": "NODE_ENV=production postcss ./src/index.css -o ./dist/main.css --verbose",
+    "test": "jest --runInBand --forceExit"
+  },
+  "jest": {
+    "testTimeout": 10000,
+    "displayName": "Content Resolution",
+    "setupFilesAfterEnv": [
+      "<rootDir>/../../jest/customMatchers.js"
+    ]
+  },
+  "devDependencies": {
+    "postcss": "^8.4.14",
+    "postcss-cli": "^9.1.0"
+  }
+}
diff --git a/integrations/content-resolution/postcss.config.js b/integrations/content-resolution/postcss.config.js
new file mode 100644
index 000000000000..4c5efe72893b
--- /dev/null
+++ b/integrations/content-resolution/postcss.config.js
@@ -0,0 +1,5 @@
+let path = require('path')
+
+module.exports = {
+  plugins: [require(path.resolve(__dirname, '..', '..'))],
+}
diff --git a/integrations/content-resolution/src/index.css b/integrations/content-resolution/src/index.css
new file mode 100644
index 000000000000..65dd5f63a7df
--- /dev/null
+++ b/integrations/content-resolution/src/index.css
@@ -0,0 +1 @@
+@tailwind utilities;
diff --git a/integrations/content-resolution/src/real/no-1.js b/integrations/content-resolution/src/real/no-1.js
new file mode 100644
index 000000000000..7953cad0c416
--- /dev/null
+++ b/integrations/content-resolution/src/real/no-1.js
@@ -0,0 +1 @@
+// content-[real-static-negative]
diff --git a/integrations/content-resolution/src/real/no.js b/integrations/content-resolution/src/real/no.js
new file mode 100644
index 000000000000..76e0cb00bae4
--- /dev/null
+++ b/integrations/content-resolution/src/real/no.js
@@ -0,0 +1 @@
+// content-[real-dynamic-negative]
diff --git a/integrations/content-resolution/src/real/yes.html b/integrations/content-resolution/src/real/yes.html
new file mode 100644
index 000000000000..48acef1f7f39
--- /dev/null
+++ b/integrations/content-resolution/src/real/yes.html
@@ -0,0 +1 @@
+<!-- content-[real-static-positive] -->
diff --git a/integrations/content-resolution/src/real/yes.js b/integrations/content-resolution/src/real/yes.js
new file mode 100644
index 000000000000..8fc42639113b
--- /dev/null
+++ b/integrations/content-resolution/src/real/yes.js
@@ -0,0 +1 @@
+// content-[real-dynamic-positive]
diff --git a/integrations/content-resolution/src/resolved/no-1.js b/integrations/content-resolution/src/resolved/no-1.js
new file mode 100644
index 000000000000..af079f767673
--- /dev/null
+++ b/integrations/content-resolution/src/resolved/no-1.js
@@ -0,0 +1 @@
+// content-[resolved-static-negative]
diff --git a/integrations/content-resolution/src/resolved/no.js b/integrations/content-resolution/src/resolved/no.js
new file mode 100644
index 000000000000..20ab72ef4ec6
--- /dev/null
+++ b/integrations/content-resolution/src/resolved/no.js
@@ -0,0 +1 @@
+// content-[resolved-dynamic-negative]
diff --git a/integrations/content-resolution/src/resolved/yes.html b/integrations/content-resolution/src/resolved/yes.html
new file mode 100644
index 000000000000..e4abd8e82dec
--- /dev/null
+++ b/integrations/content-resolution/src/resolved/yes.html
@@ -0,0 +1 @@
+<!-- content-[resolved-static-positive] -->
diff --git a/integrations/content-resolution/src/resolved/yes.js b/integrations/content-resolution/src/resolved/yes.js
new file mode 100644
index 000000000000..b33de482b4b3
--- /dev/null
+++ b/integrations/content-resolution/src/resolved/yes.js
@@ -0,0 +1 @@
+// content-[resolved-dynamic-positive]
diff --git a/integrations/content-resolution/tests/config.js b/integrations/content-resolution/tests/config.js
new file mode 100644
index 000000000000..6f707d292a72
--- /dev/null
+++ b/integrations/content-resolution/tests/config.js
@@ -0,0 +1,53 @@
+// @ts-config
+
+let fs = require('fs')
+let path = require('path')
+
+module.exports.writeConfigs = async function writeConfigs({
+  both = {},
+  inRoot = {},
+  inDir = {},
+} = {}) {
+  let configs = [
+    {
+      path: '../tailwind.config.js',
+      config: {
+        ...both,
+        ...inRoot,
+        content: {
+          files: [],
+          ...both.content,
+          ...inRoot.content,
+        },
+      },
+    },
+    {
+      path: '../src/tailwind.config.js',
+      config: {
+        ...both,
+        ...inDir,
+        content: {
+          files: [],
+          ...both.content,
+          ...inDir.content,
+        },
+      },
+    },
+  ]
+
+  let defaultConfig = {
+    corePlugins: { preflight: false },
+  }
+
+  for (const config of configs) {
+    await fs.promises.writeFile(
+      path.resolve(__dirname, config.path),
+      `module.exports = ${JSON.stringify({ ...defaultConfig, ...config.config })};`
+    )
+  }
+}
+
+module.exports.destroyConfigs = async function destroyConfigs() {
+  await fs.promises.unlink(path.resolve(__dirname, '../tailwind.config.js'))
+  await fs.promises.unlink(path.resolve(__dirname, '../src/tailwind.config.js'))
+}
diff --git a/integrations/content-resolution/tests/content.test.js b/integrations/content-resolution/tests/content.test.js
new file mode 100644
index 000000000000..5af090827b3b
--- /dev/null
+++ b/integrations/content-resolution/tests/content.test.js
@@ -0,0 +1,287 @@
+let fs = require('fs')
+let path = require('path')
+let { cwd } = require('./cwd.js')
+let { writeConfigs, destroyConfigs } = require('./config.js')
+
+let $ = require('../../execute')
+let { css } = require('../../syntax')
+
+let { readOutputFile } = require('../../io')({
+  output: 'dist',
+  input: '.',
+})
+
+// Write default configs before running tests and remove them afterwards
+beforeAll(() => writeConfigs())
+afterAll(() => destroyConfigs())
+
+// Create a symlink at ./src/link that points to ./src/resolved and remove it afterwards
+beforeAll(() =>
+  fs.promises.symlink(
+    path.resolve(__dirname, '../src/resolved'),
+    path.resolve(__dirname, '../src/link')
+  )
+)
+afterAll(async () => {
+  try {
+    await fs.promises.unlink(path.resolve(__dirname, '../src/link'))
+  } catch {}
+})
+
+// If we've changed directories reset the cwd back to what it was before running these tests
+afterEach(() => cwd.unwind())
+
+async function build({ cwd: cwdPath } = {}) {
+  let inputPath = path.resolve(__dirname, '../src/index.css')
+  let outputPath = path.resolve(__dirname, '../dist/main.css')
+
+  await cwd.switch(cwdPath)
+
+  // Note that ./tailwind.config.js is hardcoded on purpose here
+  // It represents a config but one that could be in different places
+  await $(`postcss ${inputPath} -o ${outputPath}`, {
+    env: { NODE_ENV: 'production' },
+    cwd: cwdPath,
+  })
+
+  return {
+    css: await readOutputFile('main.css'),
+  }
+}
+
+it('looks in the CWD by default', async () => {
+  await writeConfigs({
+    both: {
+      content: {
+        files: ['./src/real/yes.html'],
+      },
+    },
+  })
+
+  let result = await build({ cwd: path.resolve(__dirname, '..') })
+
+  expect(result.css).toMatchCss(css`
+    .content-\[real-static-positive\] {
+      --tw-content: real-static-positive;
+      content: var(--tw-content);
+    }
+  `)
+
+  result = await build({ cwd: path.resolve(__dirname, '../src') })
+
+  expect(result.css).toMatchCss(``)
+})
+
+it('looks in the CWD for non-config-relative paths', async () => {
+  await writeConfigs({
+    both: {
+      // Turn it on by default (eventual v4 behavior)
+      experimental: { relativeContentPathsByDefault: true },
+
+      // But then disable it anyway
+      content: {
+        relative: false,
+        files: ['./src/real/yes.html'],
+      },
+    },
+  })
+
+  let result = await build({ cwd: path.resolve(__dirname, '..') })
+
+  expect(result.css).toMatchCss(css`
+    .content-\[real-static-positive\] {
+      --tw-content: real-static-positive;
+      content: var(--tw-content);
+    }
+  `)
+
+  result = await build({ cwd: path.resolve(__dirname, '../src') })
+
+  expect(result.css).toMatchCss(``)
+})
+
+it('can look for content files relative to the config', async () => {
+  await writeConfigs({
+    both: {
+      content: {
+        relative: true,
+        files: ['./real/yes.html'],
+      },
+    },
+  })
+
+  // Here `./real` doesn't exist next to the config in the root directory
+  let result = await build({ cwd: path.resolve(__dirname, '..') })
+
+  expect(result.css).toMatchCss(css``)
+
+  // But here it `./real` does exist next to the config in the `./src` directory!
+  result = await build({ cwd: path.resolve(__dirname, '../src') })
+
+  expect(result.css).toMatchCss(css`
+    .content-\[real-static-positive\] {
+      --tw-content: real-static-positive;
+      content: var(--tw-content);
+    }
+  `)
+})
+
+it('it handles ignored globs correctly when not relative to the config', async () => {
+  await writeConfigs({
+    both: {
+      content: {
+        relative: false,
+        files: [
+          './src/real/yes.html', // Scanned + static
+          './src/real/*.js', // Scanned + dynamic
+          '!./src/real/no.js', // Ignored + static
+          '!./src/real/no-*.js', // Ignored + dynamic
+        ],
+      },
+    },
+  })
+
+  let result = await build({ cwd: path.resolve(__dirname, '..') })
+
+  expect(result.css).toMatchCss(css`
+    .content-\[real-static-positive\] {
+      --tw-content: real-static-positive;
+      content: var(--tw-content);
+    }
+    .content-\[real-dynamic-positive\] {
+      --tw-content: real-dynamic-positive;
+      content: var(--tw-content);
+    }
+  `)
+
+  // But here it `./real` does exist next to the config in the `./src` directory!
+  result = await build({ cwd: path.resolve(__dirname, '../src') })
+
+  expect(result.css).toMatchCss(``)
+})
+
+it('it handles ignored globs correctly when relative to the config', async () => {
+  await writeConfigs({
+    both: {
+      content: {
+        relative: true,
+        files: [
+          './real/yes.html', // Scanned + static
+          './real/*.js', // Scanned + dynamic
+          '!./real/no.js', // Ignored + static
+          '!./real/no-*.js', // Ignored + dynamic
+        ],
+      },
+    },
+  })
+
+  let result = await build({ cwd: path.resolve(__dirname, '..') })
+
+  expect(result.css).toMatchCss(``)
+
+  // But here it `./real` does exist next to the config in the `./src` directory!
+  result = await build({ cwd: path.resolve(__dirname, '../src') })
+
+  expect(result.css).toMatchCss(css`
+    .content-\[real-static-positive\] {
+      --tw-content: real-static-positive;
+      content: var(--tw-content);
+    }
+    .content-\[real-dynamic-positive\] {
+      --tw-content: real-dynamic-positive;
+      content: var(--tw-content);
+    }
+  `)
+})
+
+it('it can resolve symlinks for files when not relative to the config', async () => {
+  await writeConfigs({
+    both: {
+      content: {
+        relative: false,
+        files: [
+          './src/real/yes.html', // Scanned + static
+          './src/real/*.js', // Scanned + dynamic
+          './src/link/yes.html', // Scanned + static + symlinked
+          './src/link/*.js', // Scanned + dynamic + symlinked
+          '!./src/real/no.js', // Ignored + static
+          '!./src/real/no-*.js', // Ignored + dynamic
+          '!./src/link/no.js', // Ignored + static + symlinked
+          '!./src/link/no-*.js', // Ignored + dynamic + symlinked
+        ],
+      },
+    },
+  })
+
+  let result = await build({ cwd: path.resolve(__dirname, '..') })
+
+  expect(result.css).toMatchCss(css`
+    .content-\[real-static-positive\] {
+      --tw-content: real-static-positive;
+      content: var(--tw-content);
+    }
+    .content-\[resolved-static-positive\] {
+      --tw-content: resolved-static-positive;
+      content: var(--tw-content);
+    }
+    .content-\[real-dynamic-positive\] {
+      --tw-content: real-dynamic-positive;
+      content: var(--tw-content);
+    }
+    .content-\[resolved-dynamic-positive\] {
+      --tw-content: resolved-dynamic-positive;
+      content: var(--tw-content);
+    }
+  `)
+
+  // But here it `./real` does exist next to the config in the `./src` directory!
+  result = await build({ cwd: path.resolve(__dirname, '../src') })
+
+  expect(result.css).toMatchCss(``)
+})
+
+it('it can resolve symlinks for files when relative to the config', async () => {
+  await writeConfigs({
+    both: {
+      content: {
+        relative: true,
+        files: [
+          './real/yes.html', // Scanned + static
+          './real/*.js', // Scanned + dynamic
+          './link/yes.html', // Scanned + static + symlinked
+          './link/*.js', // Scanned + dynamic + symlinked
+          '!./real/no.js', // Ignored + static
+          '!./real/no-*.js', // Ignored + dynamic
+          '!./link/no.js', // Ignored + static + symlinked
+          '!./link/no-*.js', // Ignored + dynamic + symlinked
+        ],
+      },
+    },
+  })
+
+  let result = await build({ cwd: path.resolve(__dirname, '..') })
+
+  expect(result.css).toMatchCss(``)
+
+  // But here it `./real` does exist next to the config in the `./src` directory!
+  result = await build({ cwd: path.resolve(__dirname, '../src') })
+
+  expect(result.css).toMatchCss(css`
+    .content-\[real-static-positive\] {
+      --tw-content: real-static-positive;
+      content: var(--tw-content);
+    }
+    .content-\[resolved-static-positive\] {
+      --tw-content: resolved-static-positive;
+      content: var(--tw-content);
+    }
+    .content-\[real-dynamic-positive\] {
+      --tw-content: real-dynamic-positive;
+      content: var(--tw-content);
+    }
+    .content-\[resolved-dynamic-positive\] {
+      --tw-content: resolved-dynamic-positive;
+      content: var(--tw-content);
+    }
+  `)
+})
diff --git a/integrations/content-resolution/tests/cwd.js b/integrations/content-resolution/tests/cwd.js
new file mode 100644
index 000000000000..aeab638acb0e
--- /dev/null
+++ b/integrations/content-resolution/tests/cwd.js
@@ -0,0 +1,24 @@
+// @ts-config
+
+let stack = []
+
+module.exports.cwd = {
+  get current() {
+    return process.cwd()
+  },
+
+  async switch(dir) {
+    stack.push(process.cwd())
+    process.chdir(dir)
+  },
+
+  async restore() {
+    process.chdir(stack.pop())
+  },
+
+  async unwind() {
+    while (stack.length) {
+      this.restore()
+    }
+  },
+}
diff --git a/integrations/execute.js b/integrations/execute.js
index 7b0f7e799c23..3931151404f5 100644
--- a/integrations/execute.js
+++ b/integrations/execute.js
@@ -19,14 +19,15 @@ function debounce(fn, ms) {
 
 module.exports = function $(command, options = {}) {
   let abortController = new AbortController()
-  let cwd = resolveToolRoot()
+  let root = resolveToolRoot()
+  let cwd = options.cwd ?? root
 
   let args = options.shell
     ? [command]
     : (() => {
         let args = command.split(' ')
         command = args.shift()
-        command = command === 'node' ? command : path.resolve(cwd, 'node_modules', '.bin', command)
+        command = command === 'node' ? command : path.resolve(root, 'node_modules', '.bin', command)
         return [command, args]
       })()
 
diff --git a/integrations/tailwindcss-cli/package-lock.json b/integrations/tailwindcss-cli/package-lock.json
index e3602894561f..1bfff83a777d 100644
--- a/integrations/tailwindcss-cli/package-lock.json
+++ b/integrations/tailwindcss-cli/package-lock.json
@@ -12,13 +12,13 @@
       }
     },
     "../..": {
-      "version": "3.0.24",
+      "version": "3.1.5",
       "license": "MIT",
       "dependencies": {
-        "arg": "^5.0.1",
+        "arg": "^5.0.2",
         "chokidar": "^3.5.3",
         "color-name": "^1.1.4",
-        "detective": "^5.2.0",
+        "detective": "^5.2.1",
         "didyoumean": "^1.2.2",
         "dlv": "^1.1.3",
         "fast-glob": "^3.2.11",
@@ -36,26 +36,26 @@
         "postcss-selector-parser": "^6.0.10",
         "postcss-value-parser": "^4.2.0",
         "quick-lru": "^5.1.1",
-        "resolve": "^1.22.0"
+        "resolve": "^1.22.1"
       },
       "bin": {
         "tailwind": "lib/cli.js",
         "tailwindcss": "lib/cli.js"
       },
       "devDependencies": {
+        "@parcel/css": "^1.11.2",
         "@swc/cli": "^0.1.57",
-        "@swc/core": "^1.2.160",
+        "@swc/core": "^1.2.196",
         "@swc/jest": "^0.2.21",
         "@swc/register": "^0.1.10",
         "autoprefixer": "^10.4.7",
-        "cssnano": "^5.1.9",
-        "esbuild": "^0.14.39",
-        "eslint": "^8.15.0",
+        "esbuild": "^0.14.48",
+        "eslint": "^8.18.0",
         "eslint-config-prettier": "^8.5.0",
-        "eslint-plugin-prettier": "^4.0.0",
-        "jest": "^28.0.3",
-        "jest-diff": "^28.1.0",
-        "prettier": "^2.6.2",
+        "eslint-plugin-prettier": "^4.2.1",
+        "jest": "^28.1.2",
+        "jest-diff": "^28.1.1",
+        "prettier": "^2.7.1",
         "prettier-plugin-tailwindcss": "^0.1.11",
         "rimraf": "^3.0.0",
         "source-map-js": "^1.0.2"
@@ -76,27 +76,27 @@
     "tailwindcss": {
       "version": "file:../..",
       "requires": {
+        "@parcel/css": "^1.11.2",
         "@swc/cli": "^0.1.57",
-        "@swc/core": "^1.2.160",
+        "@swc/core": "^1.2.196",
         "@swc/jest": "^0.2.21",
         "@swc/register": "^0.1.10",
-        "arg": "^5.0.1",
+        "arg": "^5.0.2",
         "autoprefixer": "^10.4.7",
         "chokidar": "^3.5.3",
         "color-name": "^1.1.4",
-        "cssnano": "^5.1.9",
-        "detective": "^5.2.0",
+        "detective": "^5.2.1",
         "didyoumean": "^1.2.2",
         "dlv": "^1.1.3",
-        "esbuild": "^0.14.39",
-        "eslint": "^8.15.0",
+        "esbuild": "^0.14.48",
+        "eslint": "^8.18.0",
         "eslint-config-prettier": "^8.5.0",
-        "eslint-plugin-prettier": "^4.0.0",
+        "eslint-plugin-prettier": "^4.2.1",
         "fast-glob": "^3.2.11",
         "glob-parent": "^6.0.2",
         "is-glob": "^4.0.3",
-        "jest": "^28.0.3",
-        "jest-diff": "^28.1.0",
+        "jest": "^28.1.2",
+        "jest-diff": "^28.1.1",
         "lilconfig": "^2.0.5",
         "normalize-path": "^3.0.0",
         "object-hash": "^3.0.0",
@@ -108,10 +108,10 @@
         "postcss-nested": "5.0.6",
         "postcss-selector-parser": "^6.0.10",
         "postcss-value-parser": "^4.2.0",
-        "prettier": "^2.6.2",
+        "prettier": "^2.7.1",
         "prettier-plugin-tailwindcss": "^0.1.11",
         "quick-lru": "^5.1.1",
-        "resolve": "^1.22.0",
+        "resolve": "^1.22.1",
         "rimraf": "^3.0.0",
         "source-map-js": "^1.0.2"
       }
diff --git a/src/cli.js b/src/cli.js
index 2851a79f1ec3..54d03743cabf 100644
--- a/src/cli.js
+++ b/src/cli.js
@@ -19,6 +19,7 @@ import packageJson from '../package.json'
 import normalizePath from 'normalize-path'
 import micromatch from 'micromatch'
 import { validateConfig } from './util/validateConfig.js'
+import { parseCandidateFiles } from './lib/content.js'
 
 let env = {
   DEBUG: process.env.DEBUG !== undefined && process.env.DEBUG !== '0',
@@ -551,14 +552,14 @@ async function build() {
   }
 
   function extractFileGlobs(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
-        // is not watchable, so let's remove it.
-        return typeof file === 'string'
-      })
-      .map((glob) => normalizePath(glob))
+    let context = {
+      tailwindConfig: config,
+      userConfigPath: configPath,
+    }
+
+    let contentPaths = parseCandidateFiles(context, config)
+
+    return contentPaths.map((contentPath) => contentPath.pattern)
   }
 
   function extractRawContent(config) {
diff --git a/src/featureFlags.js b/src/featureFlags.js
index 5e9d73583499..a03916c5b0f8 100644
--- a/src/featureFlags.js
+++ b/src/featureFlags.js
@@ -10,8 +10,13 @@ let featureFlags = {
     'hoverOnlyWhenSupported',
     'respectDefaultRingColorOpacity',
     'disableColorOpacityUtilitiesByDefault',
+    'relativeContentPathsByDefault',
+  ],
+  experimental: [
+    'optimizeUniversalDefaults',
+    'matchVariant',
+    // 'variantGrouping',
   ],
-  experimental: ['optimizeUniversalDefaults', 'matchVariant' /* , 'variantGrouping' */],
 }
 
 export function flagEnabled(config, flag) {
diff --git a/src/lib/content.js b/src/lib/content.js
new file mode 100644
index 000000000000..475706e0b47d
--- /dev/null
+++ b/src/lib/content.js
@@ -0,0 +1,199 @@
+// @ts-check
+
+import fs from 'fs'
+import path from 'path'
+import isGlob from 'is-glob'
+import fastGlob from 'fast-glob'
+import normalizePath from 'normalize-path'
+import { parseGlob } from '../util/parseGlob'
+import { env } from './sharedState'
+
+/** @typedef {import('../../types/config.js').RawFile} RawFile */
+/** @typedef {import('../../types/config.js').FilePath} FilePath */
+
+/**
+ * @typedef {object} ContentPath
+ * @property {string} original
+ * @property {string} base
+ * @property {string | null} glob
+ * @property {boolean} ignore
+ * @property {string} pattern
+ */
+
+/**
+ * Turn a list of content paths (absolute or not; glob or not) into a list of
+ * absolute file paths that exist on the filesystem
+ *
+ * If there are symlinks in the path then multiple paths will be returned
+ * one for the symlink and one for the actual file
+ *
+ * @param {*} context
+ * @param {import('tailwindcss').Config} tailwindConfig
+ * @returns {ContentPath[]}
+ */
+export function parseCandidateFiles(context, tailwindConfig) {
+  let files = tailwindConfig.content.files
+
+  // Normalize the file globs
+  files = files.filter((filePath) => typeof filePath === 'string')
+  files = files.map(normalizePath)
+
+  // Split into included and excluded globs
+  let tasks = fastGlob.generateTasks(files)
+
+  /** @type {ContentPath[]} */
+  let included = []
+
+  /** @type {ContentPath[]} */
+  let excluded = []
+
+  for (const task of tasks) {
+    included.push(...task.positive.map((filePath) => parseFilePath(filePath, false)))
+    excluded.push(...task.negative.map((filePath) => parseFilePath(filePath, true)))
+  }
+
+  let paths = [...included, ...excluded]
+
+  // Resolve paths relative to the config file or cwd
+  paths = resolveRelativePaths(context, paths)
+
+  // Resolve symlinks if possible
+  paths = paths.flatMap(resolvePathSymlinks)
+
+  // Update cached patterns
+  paths = paths.map(resolveGlobPattern)
+
+  return paths
+}
+
+/**
+ *
+ * @param {string} filePath
+ * @param {boolean} ignore
+ * @returns {ContentPath}
+ */
+function parseFilePath(filePath, ignore) {
+  let contentPath = {
+    original: filePath,
+    base: filePath,
+    ignore,
+    pattern: filePath,
+    glob: null,
+  }
+
+  if (isGlob(filePath)) {
+    Object.assign(contentPath, parseGlob(filePath))
+  }
+
+  return contentPath
+}
+
+/**
+ *
+ * @param {ContentPath} contentPath
+ * @returns {ContentPath}
+ */
+function resolveGlobPattern(contentPath) {
+  contentPath.pattern = contentPath.glob
+    ? `${contentPath.base}/${contentPath.glob}`
+    : contentPath.base
+
+  contentPath.pattern = contentPath.ignore ? `!${contentPath.pattern}` : contentPath.pattern
+
+  return contentPath
+}
+
+/**
+ * Resolve each path relative to the config file (when possible) if the experimental flag is enabled
+ * Otherwise, resolve relative to the current working directory
+ *
+ * @param {any} context
+ * @param {ContentPath[]} contentPaths
+ * @returns {ContentPath[]}
+ */
+function resolveRelativePaths(context, contentPaths) {
+  let resolveFrom = []
+
+  // Resolve base paths relative to the config file (when possible) if the experimental flag is enabled
+  if (context.userConfigPath && context.tailwindConfig.content.relative) {
+    resolveFrom = [path.dirname(context.userConfigPath)]
+  }
+
+  return contentPaths.map((contentPath) => {
+    contentPath.base = path.resolve(...resolveFrom, contentPath.base)
+
+    return contentPath
+  })
+}
+
+/**
+ * Resolve the symlink for the base directory / file in each path
+ * These are added as additional dependencies to watch for changes because
+ * some tools (like webpack) will only watch the actual file or directory
+ * but not the symlink itself even in projects that use monorepos.
+ *
+ * @param {ContentPath} contentPath
+ * @returns {ContentPath[]}
+ */
+function resolvePathSymlinks(contentPath) {
+  let paths = [contentPath]
+
+  try {
+    let resolvedPath = fs.realpathSync(contentPath.base)
+    if (resolvedPath !== contentPath.base) {
+      paths.push({
+        ...contentPath,
+        base: resolvedPath,
+      })
+    }
+  } catch {
+    // TODO: log this?
+  }
+
+  return paths
+}
+
+/**
+ * @param {any} context
+ * @param {ContentPath[]} candidateFiles
+ * @param {Map<string, number>} fileModifiedMap
+ * @returns {{ content: string, extension: string }[]}
+ */
+export function resolvedChangedContent(context, candidateFiles, fileModifiedMap) {
+  let changedContent = context.tailwindConfig.content.files
+    .filter((item) => typeof item.raw === 'string')
+    .map(({ raw, extension = 'html' }) => ({ content: raw, extension }))
+
+  for (let changedFile of resolveChangedFiles(candidateFiles, fileModifiedMap)) {
+    let content = fs.readFileSync(changedFile, 'utf8')
+    let extension = path.extname(changedFile).slice(1)
+    changedContent.push({ content, extension })
+  }
+
+  return changedContent
+}
+
+/**
+ *
+ * @param {ContentPath[]} candidateFiles
+ * @param {Map<string, number>} fileModifiedMap
+ * @returns {Set<string>}
+ */
+function resolveChangedFiles(candidateFiles, fileModifiedMap) {
+  let paths = candidateFiles.map((contentPath) => contentPath.pattern)
+
+  let changedFiles = new Set()
+  env.DEBUG && console.time('Finding changed files')
+  let files = fastGlob.sync(paths, { absolute: true })
+  for (let file of files) {
+    let prevModified = fileModifiedMap.has(file) ? fileModifiedMap.get(file) : -Infinity
+    let modified = fs.statSync(file).mtimeMs
+
+    if (modified > prevModified) {
+      changedFiles.add(file)
+      fileModifiedMap.set(file, modified)
+    }
+  }
+  env.DEBUG && console.timeEnd('Finding changed files')
+  return changedFiles
+}
diff --git a/src/lib/setupContextUtils.js b/src/lib/setupContextUtils.js
index 2b8c095022ec..d15e8db8c70c 100644
--- a/src/lib/setupContextUtils.js
+++ b/src/lib/setupContextUtils.js
@@ -1000,6 +1000,10 @@ export function getContext(
 
   let context = createContext(tailwindConfig, [], root)
 
+  Object.assign(context, {
+    userConfigPath,
+  })
+
   trackModified([...contextDependencies], getFileModifiedMap(context))
 
   // ---
diff --git a/src/lib/setupTrackingContext.js b/src/lib/setupTrackingContext.js
index 37b42cdbae20..3e51bd9e15d6 100644
--- a/src/lib/setupTrackingContext.js
+++ b/src/lib/setupTrackingContext.js
@@ -1,22 +1,14 @@
 import fs from 'fs'
-import path from 'path'
-
-import fastGlob from 'fast-glob'
 import LRU from 'quick-lru'
-import normalizePath from 'normalize-path'
 
 import hash from '../util/hashConfig'
 import getModuleDependencies from '../lib/getModuleDependencies'
-
 import resolveConfig from '../public/resolve-config'
-
 import resolveConfigPath from '../util/resolveConfigPath'
-
-import { env } from './sharedState'
-
 import { getContext, getFileModifiedMap } from './setupContextUtils'
 import parseDependency from '../util/parseDependency'
 import { validateConfig } from '../util/validateConfig.js'
+import { parseCandidateFiles, resolvedChangedContent } from './content.js'
 
 let configPathCache = new LRU({ maxSize: 100 })
 
@@ -27,9 +19,7 @@ function getCandidateFiles(context, tailwindConfig) {
     return candidateFilesCache.get(context)
   }
 
-  let candidateFiles = tailwindConfig.content.files
-    .filter((item) => typeof item === 'string')
-    .map((contentPath) => normalizePath(contentPath))
+  let candidateFiles = parseCandidateFiles(context, tailwindConfig)
 
   return candidateFilesCache.set(context, candidateFiles).get(context)
 }
@@ -80,36 +70,6 @@ function getTailwindConfig(configOrPath) {
   return [newConfig, null, hash(newConfig), []]
 }
 
-function resolvedChangedContent(context, candidateFiles, fileModifiedMap) {
-  let changedContent = context.tailwindConfig.content.files
-    .filter((item) => typeof item.raw === 'string')
-    .map(({ raw, extension = 'html' }) => ({ content: raw, extension }))
-
-  for (let changedFile of resolveChangedFiles(candidateFiles, fileModifiedMap)) {
-    let content = fs.readFileSync(changedFile, 'utf8')
-    let extension = path.extname(changedFile).slice(1)
-    changedContent.push({ content, extension })
-  }
-  return changedContent
-}
-
-function resolveChangedFiles(candidateFiles, fileModifiedMap) {
-  let changedFiles = new Set()
-  env.DEBUG && console.time('Finding changed files')
-  let files = fastGlob.sync(candidateFiles, { absolute: true })
-  for (let file of files) {
-    let prevModified = fileModifiedMap.has(file) ? fileModifiedMap.get(file) : -Infinity
-    let modified = fs.statSync(file).mtimeMs
-
-    if (modified > prevModified) {
-      changedFiles.add(file)
-      fileModifiedMap.set(file, modified)
-    }
-  }
-  env.DEBUG && console.timeEnd('Finding changed files')
-  return changedFiles
-}
-
 // DISABLE_TOUCH = TRUE
 
 // Retrieve an existing context from cache if possible (since contexts are unique per
@@ -161,9 +121,8 @@ export default function setupTrackingContext(configOrPath) {
         let fileModifiedMap = getFileModifiedMap(context)
 
         // Add template paths as postcss dependencies.
-        for (let fileOrGlob of candidateFiles) {
-          let dependency = parseDependency(fileOrGlob)
-          if (dependency) {
+        for (let contentPath of candidateFiles) {
+          for (let dependency of parseDependency(contentPath)) {
             registerDependency(dependency)
           }
         }
diff --git a/src/util/normalizeConfig.js b/src/util/normalizeConfig.js
index 2d23a864d505..baee48394d56 100644
--- a/src/util/normalizeConfig.js
+++ b/src/util/normalizeConfig.js
@@ -56,9 +56,11 @@ export function normalizeConfig(config) {
 
     // When `config.content` is an object
     if (typeof config.content === 'object' && config.content !== null) {
-      // Only `files`, `extract` and `transform` can exist in `config.content`
+      // Only `files`, `relative`, `extract`, and `transform` can exist in `config.content`
       if (
-        Object.keys(config.content).some((key) => !['files', 'extract', 'transform'].includes(key))
+        Object.keys(config.content).some(
+          (key) => !['files', 'relative', 'extract', 'transform'].includes(key)
+        )
       ) {
         return false
       }
@@ -112,6 +114,14 @@ export function normalizeConfig(config) {
         ) {
           return false
         }
+
+        // `config.content.relative` is optional and can be a boolean
+        if (
+          typeof config.content.relative !== 'boolean' &&
+          typeof config.content.relative !== 'undefined'
+        ) {
+          return false
+        }
       }
 
       return true
@@ -154,6 +164,16 @@ export function normalizeConfig(config) {
 
   // Normalize the `content`
   config.content = {
+    relative: (() => {
+      let { content } = config
+
+      if (content?.relative) {
+        return content.relative
+      }
+
+      return config.future?.relativeContentPathsByDefault ?? false
+    })(),
+
     files: (() => {
       let { content, purge } = config
 
diff --git a/src/util/parseDependency.js b/src/util/parseDependency.js
index 1051df473357..f26eb1a29b15 100644
--- a/src/util/parseDependency.js
+++ b/src/util/parseDependency.js
@@ -1,49 +1,44 @@
-import isGlob from 'is-glob'
-import globParent from 'glob-parent'
-import path from 'path'
-
-// Based on `glob-base`
-// https://github.com/micromatch/glob-base/blob/master/index.js
-function parseGlob(pattern) {
-  let glob = pattern
-  let base = globParent(pattern)
-
-  if (base !== '.') {
-    glob = pattern.substr(base.length)
-    if (glob.charAt(0) === '/') {
-      glob = glob.substr(1)
-    }
-  }
-
-  if (glob.substr(0, 2) === './') {
-    glob = glob.substr(2)
-  }
-  if (glob.charAt(0) === '/') {
-    glob = glob.substr(1)
+// @ts-check
+
+/**
+ * @typedef {{type: 'dependency', file: string} | {type: 'dir-dependency', dir: string, glob: string}} Dependency
+ */
+
+/**
+ *
+ * @param {import('../lib/content.js').ContentPath} contentPath
+ * @returns {Dependency[]}
+ */
+export default function parseDependency(contentPath) {
+  if (contentPath.ignore) {
+    return []
   }
 
-  return { base, glob }
-}
-
-export default function parseDependency(normalizedFileOrGlob) {
-  if (normalizedFileOrGlob.startsWith('!')) {
-    return null
-  }
-
-  let message
-
-  if (isGlob(normalizedFileOrGlob)) {
-    let { base, glob } = parseGlob(normalizedFileOrGlob)
-    message = { type: 'dir-dependency', dir: path.resolve(base), glob }
-  } else {
-    message = { type: 'dependency', file: path.resolve(normalizedFileOrGlob) }
+  if (!contentPath.glob) {
+    return [
+      {
+        type: 'dependency',
+        file: contentPath.base,
+      },
+    ]
   }
 
-  // rollup-plugin-postcss does not support dir-dependency messages
-  // but directories can be watched in the same way as files
-  if (message.type === 'dir-dependency' && process.env.ROLLUP_WATCH === 'true') {
-    message = { type: 'dependency', file: message.dir }
+  if (process.env.ROLLUP_WATCH === 'true') {
+    // rollup-plugin-postcss does not support dir-dependency messages
+    // but directories can be watched in the same way as files
+    return [
+      {
+        type: 'dependency',
+        file: contentPath.base,
+      },
+    ]
   }
 
-  return message
+  return [
+    {
+      type: 'dir-dependency',
+      dir: contentPath.base,
+      glob: contentPath.glob,
+    },
+  ]
 }
diff --git a/src/util/parseGlob.js b/src/util/parseGlob.js
new file mode 100644
index 000000000000..5c03f413d7e2
--- /dev/null
+++ b/src/util/parseGlob.js
@@ -0,0 +1,24 @@
+import globParent from 'glob-parent'
+
+// Based on `glob-base`
+// https://github.com/micromatch/glob-base/blob/master/index.js
+export function parseGlob(pattern) {
+  let glob = pattern
+  let base = globParent(pattern)
+
+  if (base !== '.') {
+    glob = pattern.substr(base.length)
+    if (glob.charAt(0) === '/') {
+      glob = glob.substr(1)
+    }
+  }
+
+  if (glob.substr(0, 2) === './') {
+    glob = glob.substr(2)
+  }
+  if (glob.charAt(0) === '/') {
+    glob = glob.substr(1)
+  }
+
+  return { base, glob }
+}
diff --git a/tests/normalize-config.test.js b/tests/normalize-config.test.js
index 71f304ea84ba..1b422a4bd4c6 100644
--- a/tests/normalize-config.test.js
+++ b/tests/normalize-config.test.js
@@ -105,6 +105,7 @@ it('should keep content files with globs', () => {
 
   expect(normalizeConfig(resolveConfig(config)).content).toEqual({
     files: ['./example-folder/**/*.{html,js}'],
+    relative: false,
     extract: {},
     transform: {},
   })
@@ -129,6 +130,7 @@ it('should warn when we detect invalid globs with incorrect brace expansion', ()
       './{example-folder}/**/*.{html}',
       './example-folder/**/*.{html}',
     ],
+    relative: false,
     extract: {},
     transform: {},
   })
diff --git a/types/config.d.ts b/types/config.d.ts
index 855b9bb02199..806cde42ab9e 100644
--- a/types/config.d.ts
+++ b/types/config.d.ts
@@ -31,6 +31,7 @@ type ContentConfig =
   | (FilePath | RawFile)[]
   | {
       files: (FilePath | RawFile)[]
+      relative?: boolean
       extract?: ExtractorFn | { [extension: string]: ExtractorFn }
       transform?: TransformerFn | { [extension: string]: TransformerFn }
     }
@@ -56,20 +57,24 @@ type SafelistConfig =
 type PresetsConfig = Config[]
 
 // Future related config
-type FutureConfigValues = never // Replace with 'future-feature-1' | 'future-feature-2'
+type FutureConfigValues =
+  | 'hoverOnlyWhenSupported'
+  | 'respectDefaultRingColorOpacity'
+  | 'disableColorOpacityUtilitiesByDefault'
+  | 'relativeContentPathsByDefault'
 type FutureConfig = Expand<'all' | Partial<Record<FutureConfigValues, boolean>>> | []
 
 // Experimental related config
-type ExperimentalConfigValues = 'optimizeUniversalDefaults' // Replace with 'experimental-feature-1' | 'experimental-feature-2'
+type ExperimentalConfigValues = 'optimizeUniversalDefaults' | 'matchVariant'
 type ExperimentalConfig = Expand<'all' | Partial<Record<ExperimentalConfigValues, boolean>>> | []
 
 // DarkMode related config
 type DarkModeConfig =
   // Use the `media` query strategy.
   | 'media'
-  // Use the `class` stategy, which requires a `.dark` class on the `html`.
+  // Use the `class` strategy, which requires a `.dark` class on the `html`.
   | 'class'
-  // Use the `class` stategy with a custom class instead of `.dark`.
+  // Use the `class` strategy with a custom class instead of `.dark`.
   | ['class', string]
 
 type Screen = { raw: string } | { min: string } | { max: string } | { min: string; max: string }