diff --git a/src/lib/setupContextUtils.js b/src/lib/setupContextUtils.js
index 6f563efb316d..ed7c974d4940 100644
--- a/src/lib/setupContextUtils.js
+++ b/src/lib/setupContextUtils.js
@@ -9,13 +9,14 @@ import parseObjectStyles from '../util/parseObjectStyles'
 import prefixSelector from '../util/prefixSelector'
 import isPlainObject from '../util/isPlainObject'
 import escapeClassName from '../util/escapeClassName'
-import nameClass from '../util/nameClass'
+import nameClass, { formatClass } from '../util/nameClass'
 import { coerceValue } from '../util/pluginUtils'
 import bigSign from '../util/bigSign'
 import * as corePlugins from '../corePlugins'
 import * as sharedState from './sharedState'
 import { env } from './sharedState'
 import { toPath } from '../util/toPath'
+import log from '../util/log'
 
 function insertInto(list, value, { before = [] } = {}) {
   before = [].concat(before)
@@ -146,7 +147,7 @@ function isValidArbitraryValue(value) {
   return true
 }
 
-function buildPluginApi(tailwindConfig, context, { variantList, variantMap, offsets }) {
+function buildPluginApi(tailwindConfig, context, { variantList, variantMap, offsets, classList }) {
   function getConfigValue(path, defaultValue) {
     return path ? dlv(tailwindConfig, path, defaultValue) : tailwindConfig
   }
@@ -241,6 +242,8 @@ function buildPluginApi(tailwindConfig, context, { variantList, variantMap, offs
         let prefixedIdentifier = prefixIdentifier(identifier, options)
         let offset = offsets.components++
 
+        classList.add(prefixedIdentifier)
+
         if (!context.candidateRuleMap.has(prefixedIdentifier)) {
           context.candidateRuleMap.set(prefixedIdentifier, [])
         }
@@ -268,6 +271,8 @@ function buildPluginApi(tailwindConfig, context, { variantList, variantMap, offs
         let prefixedIdentifier = prefixIdentifier(identifier, options)
         let offset = offsets.utilities++
 
+        classList.add(prefixedIdentifier)
+
         if (!context.candidateRuleMap.has(prefixedIdentifier)) {
           context.candidateRuleMap.set(prefixedIdentifier, [])
         }
@@ -293,6 +298,8 @@ function buildPluginApi(tailwindConfig, context, { variantList, variantMap, offs
         let prefixedIdentifier = prefixIdentifier(identifier, options)
         let rule = utilities[identifier]
 
+        classList.add([prefixedIdentifier, options])
+
         function wrapped(modifier) {
           let { type = 'any' } = options
           type = [].concat(type)
@@ -468,10 +475,13 @@ function registerPlugins(plugins, context) {
     user: 0n,
   }
 
+  let classList = new Set()
+
   let pluginApi = buildPluginApi(context.tailwindConfig, context, {
     variantList,
     variantMap,
     offsets,
+    classList,
   })
 
   for (let plugin of plugins) {
@@ -523,6 +533,83 @@ function registerPlugins(plugins, context) {
       variantFunctions.map((variantFunction, idx) => [sort << BigInt(idx), variantFunction])
     )
   }
+
+  //
+  let warnedAbout = new Set([])
+  context.safelist = function () {
+    let safelist = (context.tailwindConfig.safelist ?? []).filter(Boolean)
+    if (safelist.length <= 0) return []
+
+    let output = []
+    let checks = []
+
+    for (let value of safelist) {
+      if (typeof value === 'string') {
+        output.push(value)
+        continue
+      }
+
+      if (value instanceof RegExp) {
+        if (!warnedAbout.has('root-regex')) {
+          log.warn([
+            // TODO: Improve this warning message
+            'RegExp in the safelist option is not supported.',
+            'Please use the object syntax instead: https://tailwindcss.com/docs/...',
+          ])
+          warnedAbout.add('root-regex')
+        }
+        continue
+      }
+
+      checks.push(value)
+    }
+
+    if (checks.length <= 0) return output.map((value) => ({ raw: value, extension: 'html' }))
+
+    let patternMatchingCount = new Map()
+
+    for (let util of classList) {
+      let utils = Array.isArray(util)
+        ? (() => {
+            let [utilName, options] = util
+            return Object.keys(options?.values ?? {}).map((value) => formatClass(utilName, value))
+          })()
+        : [util]
+
+      for (let util of utils) {
+        for (let { pattern, variants = [] } of checks) {
+          // RegExp with the /g flag are stateful, so let's reset the last
+          // index pointer to reset the state.
+          pattern.lastIndex = 0
+
+          if (!patternMatchingCount.has(pattern)) {
+            patternMatchingCount.set(pattern, 0)
+          }
+
+          if (!pattern.test(util)) continue
+
+          patternMatchingCount.set(pattern, patternMatchingCount.get(pattern) + 1)
+
+          output.push(util)
+          for (let variant of variants) {
+            output.push(variant + context.tailwindConfig.separator + util)
+          }
+        }
+      }
+    }
+
+    for (let [regex, count] of patternMatchingCount.entries()) {
+      if (count !== 0) continue
+
+      log.warn([
+        // TODO: Improve this warning message
+        `You have a regex pattern in your "safelist" config (${regex}) that doesn't match any utilities.`,
+        'For more info, visit https://tailwindcss.com/docs/...',
+      ])
+    }
+
+    return output.map((value) => ({ raw: value, extension: 'html' }))
+  }
 }
 
 export function createContext(
diff --git a/src/lib/setupTrackingContext.js b/src/lib/setupTrackingContext.js
index f0ea6ab2616d..9b1e71ec071c 100644
--- a/src/lib/setupTrackingContext.js
+++ b/src/lib/setupTrackingContext.js
@@ -80,6 +80,7 @@ function resolvedChangedContent(context, candidateFiles, fileModifiedMap) {
   let changedContent = context.tailwindConfig.content.content
     .filter((item) => typeof item.raw === 'string')
     .concat(context.tailwindConfig.content.safelist)
+    .concat(context.safelist())
     .map(({ raw, extension }) => ({ content: raw, extension }))
 
   for (let changedFile of resolveChangedFiles(candidateFiles, fileModifiedMap)) {
diff --git a/src/lib/setupWatchingContext.js b/src/lib/setupWatchingContext.js
index 4e9d772b8557..1eeeb11cf2eb 100644
--- a/src/lib/setupWatchingContext.js
+++ b/src/lib/setupWatchingContext.js
@@ -188,6 +188,7 @@ function resolvedChangedContent(context, candidateFiles) {
   let changedContent = context.tailwindConfig.content.content
     .filter((item) => typeof item.raw === 'string')
     .concat(context.tailwindConfig.content.safelist)
+    .concat(context.safelist())
     .map(({ raw, extension }) => ({ content: raw, extension }))
 
   for (let changedFile of resolveChangedFiles(context, candidateFiles)) {
diff --git a/src/util/nameClass.js b/src/util/nameClass.js
index 2bb0548bd0f9..f67b3fd581a8 100644
--- a/src/util/nameClass.js
+++ b/src/util/nameClass.js
@@ -6,17 +6,21 @@ function asClass(name) {
 }
 
 export default function nameClass(classPrefix, key) {
+  return asClass(formatClass(classPrefix, key))
+}
+
+export function formatClass(classPrefix, key) {
   if (key === 'DEFAULT') {
-    return asClass(classPrefix)
+    return classPrefix
   }
 
   if (key === '-') {
-    return asClass(`-${classPrefix}`)
+    return `-${classPrefix}`
   }
 
   if (key.startsWith('-')) {
-    return asClass(`-${classPrefix}${key}`)
+    return `-${classPrefix}${key}`
   }
 
-  return asClass(`${classPrefix}-${key}`)
+  return `${classPrefix}-${key}`
 }
diff --git a/tests/safelist.test.js b/tests/safelist.test.js
new file mode 100644
index 000000000000..6325cfad3803
--- /dev/null
+++ b/tests/safelist.test.js
@@ -0,0 +1,196 @@
+import { run, html, css } from './util/run'
+
+it('should not safelist anything', () => {
+  let config = {
+    content: [{ raw: html`<div class="uppercase"></div>` }],
+  }
+
+  return run('@tailwind utilities', config).then((result) => {
+    return expect(result.css).toMatchCss(css`
+      .uppercase {
+        text-transform: uppercase;
+      }
+    `)
+  })
+})
+
+it('should safelist strings', () => {
+  let config = {
+    content: [{ raw: html`<div class="uppercase"></div>` }],
+    safelist: ['mt-[20px]', 'font-bold', 'text-gray-200', 'hover:underline'],
+  }
+
+  return run('@tailwind utilities', config).then((result) => {
+    return expect(result.css).toMatchCss(css`
+      .mt-\\[20px\\] {
+        margin-top: 20px;
+      }
+
+      .font-bold {
+        font-weight: 700;
+      }
+
+      .uppercase {
+        text-transform: uppercase;
+      }
+
+      .text-gray-200 {
+        --tw-text-opacity: 1;
+        color: rgb(229 231 235 / var(--tw-text-opacity));
+      }
+
+      .hover\\:underline:hover {
+        text-decoration: underline;
+      }
+    `)
+  })
+})
+
+it('should safelist based on a pattern regex', () => {
+  let config = {
+    content: [{ raw: html`<div class="uppercase"></div>` }],
+    safelist: [
+      {
+        pattern: /bg-(red)-(100|200)/,
+        variants: ['hover'],
+      },
+    ],
+  }
+
+  return run('@tailwind utilities', config).then((result) => {
+    return expect(result.css).toMatchCss(css`
+      .bg-red-100 {
+        --tw-bg-opacity: 1;
+        background-color: rgb(254 226 226 / var(--tw-bg-opacity));
+      }
+
+      .bg-red-200 {
+        --tw-bg-opacity: 1;
+        background-color: rgb(254 202 202 / var(--tw-bg-opacity));
+      }
+
+      .uppercase {
+        text-transform: uppercase;
+      }
+
+      .hover\\:bg-red-100:hover {
+        --tw-bg-opacity: 1;
+        background-color: rgb(254 226 226 / var(--tw-bg-opacity));
+      }
+
+      .hover\\:bg-red-200:hover {
+        --tw-bg-opacity: 1;
+        background-color: rgb(254 202 202 / var(--tw-bg-opacity));
+      }
+    `)
+  })
+})
+
+it('should not generate duplicates', () => {
+  let config = {
+    content: [{ raw: html`<div class="uppercase"></div>` }],
+    safelist: [
+      'uppercase',
+      {
+        pattern: /bg-(red)-(100|200)/,
+        variants: ['hover'],
+      },
+      {
+        pattern: /bg-(red)-(100|200)/,
+        variants: ['hover'],
+      },
+      {
+        pattern: /bg-(red)-(100|200)/,
+        variants: ['hover'],
+      },
+    ],
+  }
+
+  return run('@tailwind utilities', config).then((result) => {
+    return expect(result.css).toMatchCss(css`
+      .bg-red-100 {
+        --tw-bg-opacity: 1;
+        background-color: rgb(254 226 226 / var(--tw-bg-opacity));
+      }
+
+      .bg-red-200 {
+        --tw-bg-opacity: 1;
+        background-color: rgb(254 202 202 / var(--tw-bg-opacity));
+      }
+
+      .uppercase {
+        text-transform: uppercase;
+      }
+
+      .hover\\:bg-red-100:hover {
+        --tw-bg-opacity: 1;
+        background-color: rgb(254 226 226 / var(--tw-bg-opacity));
+      }
+
+      .hover\\:bg-red-200:hover {
+        --tw-bg-opacity: 1;
+        background-color: rgb(254 202 202 / var(--tw-bg-opacity));
+      }
+    `)
+  })
+})
+
+it('should safelist when using a custom prefix', () => {
+  let config = {
+    prefix: 'tw-',
+    content: [{ raw: html`<div class="tw-uppercase"></div>` }],
+    safelist: [
+      {
+        pattern: /tw-bg-red-(100|200)/g,
+      },
+    ],
+  }
+
+  return run('@tailwind utilities', config).then((result) => {
+    return expect(result.css).toMatchCss(css`
+      .tw-bg-red-100 {
+        --tw-bg-opacity: 1;
+        background-color: rgb(254 226 226 / var(--tw-bg-opacity));
+      }
+
+      .tw-bg-red-200 {
+        --tw-bg-opacity: 1;
+        background-color: rgb(254 202 202 / var(--tw-bg-opacity));
+      }
+
+      .tw-uppercase {
+        text-transform: uppercase;
+      }
+    `)
+  })
+})
+
+it('should not safelist when an empty list is provided', () => {
+  let config = {
+    content: [{ raw: html`<div class="uppercase"></div>` }],
+    safelist: [],
+  }
+
+  return run('@tailwind utilities', config).then((result) => {
+    return expect(result.css).toMatchCss(css`
+      .uppercase {
+        text-transform: uppercase;
+      }
+    `)
+  })
+})
+
+it('should not safelist when an sparse/holey list is provided', () => {
+  let config = {
+    content: [{ raw: html`<div class="uppercase"></div>` }],
+    safelist: [, , ,],
+  }
+
+  return run('@tailwind utilities', config).then((result) => {
+    return expect(result.css).toMatchCss(css`
+      .uppercase {
+        text-transform: uppercase;
+      }
+    `)
+  })
+})