diff --git a/src/corePlugins.js b/src/corePlugins.js
index 2bd8e9d0357a..90973cf09877 100644
--- a/src/corePlugins.js
+++ b/src/corePlugins.js
@@ -1,6 +1,7 @@
 import fs from 'fs'
 import * as path from 'path'
 import postcss from 'postcss'
+import postcssValueParser from 'postcss-value-parser'
 import createUtilityPlugin from './util/createUtilityPlugin'
 import buildMediaQuery from './util/buildMediaQuery'
 import escapeClassName from './util/escapeClassName'
@@ -208,10 +209,29 @@ export let variantPlugins = {
   },
 
   screenVariants: ({ theme, addVariant }) => {
+    let id = Symbol('screens')
+    let values = Object.values(theme('screens', {}))
+    let sort = !(
+      values.every((value) => typeof value === 'string') &&
+      new Set(values.map((value) => postcssValueParser.unit(value)?.unit ?? value)).size === 1
+    )
+      ? () => 0
+      : (a, z) => {
+          // Compare min-width screens
+          if (a.length === 1 && z.length === 1) {
+            let [{ min: aMin }] = a
+            let [{ min: zMin }] = z
+            return parseInt(aMin) - parseInt(zMin)
+          }
+
+          // Not a screen we want to even try and compare
+          return 0
+        }
+
     for (let screen of normalizeScreens(theme('screens'))) {
       let query = buildMediaQuery(screen)
 
-      addVariant(screen.name, `@media ${query}`)
+      addVariant(screen.name, `@media ${query}`, { id, sort, value: screen.values })
     }
   },
 
diff --git a/tests/responsive-and-variants-atrules.test.js b/tests/responsive-and-variants-atrules.test.js
index 4bebc73faa1a..eb6b64d77456 100644
--- a/tests/responsive-and-variants-atrules.test.js
+++ b/tests/responsive-and-variants-atrules.test.js
@@ -1,7 +1,7 @@
 import fs from 'fs'
 import path from 'path'
 
-import { run, css } from './util/run'
+import { run, css, html } from './util/run'
 
 test('responsive and variants atrules', () => {
   let config = {
@@ -79,3 +79,37 @@ test('responsive and variants atrules', () => {
     expect(result.css).toMatchFormattedCss(expected)
   })
 })
+
+it('should sort breakpoints intelligentally', () => {
+  let config = {
+    content: [{ raw: html`<div class="xs:italic md:underline"></div>` }],
+    theme: {
+      extend: {
+        screens: {
+          xs: '123px',
+        },
+      },
+    },
+    corePlugins: { preflight: false },
+  }
+
+  let input = css`
+    @tailwind utilities;
+  `
+
+  return run(input, config).then((result) => {
+    expect(result.css).toMatchFormattedCss(css`
+      @media (min-width: 123px) {
+        .xs\:italic {
+          font-style: italic;
+        }
+      }
+
+      @media (min-width: 768px) {
+        .md\:underline {
+          text-decoration-line: underline;
+        }
+      }
+    `)
+  })
+})