diff --git a/CHANGELOG.md b/CHANGELOG.md
index fa555db9f265..52d6d51f66a6 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -11,6 +11,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 - Ensure complex variants with multiple classes work ([#6311](https://github.com/tailwindlabs/tailwindcss/pull/6311))
 - Re-add `default` interop to public available functions ([#6348](https://github.com/tailwindlabs/tailwindcss/pull/6348))
+- Detect circular dependencies when using `@apply` ([#6365](https://github.com/tailwindlabs/tailwindcss/pull/6365))
 
 ## [3.0.0] - 2021-12-09
 
diff --git a/src/lib/expandApplyAtRules.js b/src/lib/expandApplyAtRules.js
index 592acb163a0b..561343266945 100644
--- a/src/lib/expandApplyAtRules.js
+++ b/src/lib/expandApplyAtRules.js
@@ -1,8 +1,24 @@
 import postcss from 'postcss'
+import parser from 'postcss-selector-parser'
 import { resolveMatches } from './generateRules'
 import bigSign from '../util/bigSign'
 import escapeClassName from '../util/escapeClassName'
 
+function containsBase(selector, classCandidateBase, separator) {
+  return parser((selectors) => {
+    let contains = false
+
+    selectors.walkClasses((classSelector) => {
+      if (classSelector.value.split(separator).pop() === classCandidateBase) {
+        contains = true
+        return false
+      }
+    })
+
+    return contains
+  }).transformSync(selector)
+}
+
 function prefix(context, selector) {
   let prefix = context.tailwindConfig.prefix
   return typeof prefix === 'function' ? prefix(selector) : prefix + selector
@@ -196,7 +212,18 @@ function processApply(root, context) {
       let siblings = []
 
       for (let [applyCandidate, important, rules] of candidates) {
+        let base = applyCandidate.split(context.tailwindConfig.separator).pop()
+
         for (let [meta, node] of rules) {
+          if (
+            containsBase(parent.selector, base, context.tailwindConfig.separator) &&
+            containsBase(node.selector, base, context.tailwindConfig.separator)
+          ) {
+            throw node.error(
+              `Circular dependency detected when using: \`@apply ${applyCandidate}\``
+            )
+          }
+
           let root = postcss.root({ nodes: [node.clone()] })
           let canRewriteSelector =
             node.type !== 'atrule' || (node.type === 'atrule' && node.name !== 'keyframes')
diff --git a/tests/apply.test.js b/tests/apply.test.js
index dd899febc4c8..d8e75138f9ba 100644
--- a/tests/apply.test.js
+++ b/tests/apply.test.js
@@ -465,3 +465,115 @@ it('should apply all the definitions of a class', () => {
     `)
   })
 })
+
+it('should throw when trying to apply a direct circular dependency', () => {
+  let config = {
+    content: [{ raw: html`<div class="foo"></div>` }],
+    plugins: [],
+  }
+
+  let input = css`
+    @tailwind components;
+    @tailwind utilities;
+
+    @layer components {
+      .foo:not(.text-red-500) {
+        @apply text-red-500;
+      }
+    }
+  `
+
+  return run(input, config).catch((err) => {
+    expect(err.reason).toBe('Circular dependency detected when using: `@apply text-red-500`')
+  })
+})
+
+it('should throw when trying to apply an indirect circular dependency', () => {
+  let config = {
+    content: [{ raw: html`<div class="a"></div>` }],
+    plugins: [],
+  }
+
+  let input = css`
+    @tailwind components;
+    @tailwind utilities;
+
+    @layer components {
+      .a {
+        @apply b;
+      }
+
+      .b {
+        @apply c;
+      }
+
+      .c {
+        @apply a;
+      }
+    }
+  `
+
+  return run(input, config).catch((err) => {
+    expect(err.reason).toBe('Circular dependency detected when using: `@apply a`')
+  })
+})
+
+it('should throw when trying to apply an indirect circular dependency with a modifier (1)', () => {
+  let config = {
+    content: [{ raw: html`<div class="a"></div>` }],
+    plugins: [],
+  }
+
+  let input = css`
+    @tailwind components;
+    @tailwind utilities;
+
+    @layer components {
+      .a {
+        @apply b;
+      }
+
+      .b {
+        @apply c;
+      }
+
+      .c {
+        @apply hover:a;
+      }
+    }
+  `
+
+  return run(input, config).catch((err) => {
+    expect(err.reason).toBe('Circular dependency detected when using: `@apply hover:a`')
+  })
+})
+
+it('should throw when trying to apply an indirect circular dependency with a modifier (2)', () => {
+  let config = {
+    content: [{ raw: html`<div class="a"></div>` }],
+    plugins: [],
+  }
+
+  let input = css`
+    @tailwind components;
+    @tailwind utilities;
+
+    @layer components {
+      .a {
+        @apply b;
+      }
+
+      .b {
+        @apply hover:c;
+      }
+
+      .c {
+        @apply a;
+      }
+    }
+  `
+
+  return run(input, config).catch((err) => {
+    expect(err.reason).toBe('Circular dependency detected when using: `@apply a`')
+  })
+})