diff --git a/src/jit/lib/expandTailwindAtRules.js b/src/jit/lib/expandTailwindAtRules.js
index 12abf8faee22..3e9bef4f9c0b 100644
--- a/src/jit/lib/expandTailwindAtRules.js
+++ b/src/jit/lib/expandTailwindAtRules.js
@@ -6,7 +6,13 @@ import cloneNodes from '../../util/cloneNodes'
 let env = sharedState.env
 let contentMatchCache = sharedState.contentMatchCache
 
-const BROAD_MATCH_GLOBAL_REGEXP = /([^<>"'`\s]*\[[^<>\s]+\])|([^<>"'`\s]*[^<>"'`\s:])/g
+const PATTERNS = [
+  "([^<>\"'`\\s]*\\['[^<>\"'`\\s]*'\\])", // `content-['hello']` but not `content-['hello']']`
+  '([^<>"\'`\\s]*\\["[^<>"\'`\\s]*"\\])', // `content-["hello"]` but not `content-["hello"]"]`
+  '([^<>"\'`\\s]*\\[[^<>"\'`\\s]+\\])', // `fill-[#bada55]`
+  '([^<>"\'`\\s]*[^<>"\'`\\s:])', // `px-1.5`, `uppercase` but not `uppercase:`
+].join('|')
+const BROAD_MATCH_GLOBAL_REGEXP = new RegExp(PATTERNS, 'g')
 const INNER_MATCH_GLOBAL_REGEXP = /[^<>"'`\s.(){}[\]#=%]*[^<>"'`\s.(){}[\]#=%:]/g
 
 const builtInExtractors = {
diff --git a/tests/jit/extractor-edge-cases.test.js b/tests/jit/extractor-edge-cases.test.js
new file mode 100644
index 000000000000..88fac0c156fa
--- /dev/null
+++ b/tests/jit/extractor-edge-cases.test.js
@@ -0,0 +1,57 @@
+import postcss from 'postcss'
+import path from 'path'
+import tailwind from '../../src/jit/index.js'
+
+function run(input, config = {}) {
+  const { currentTestName } = expect.getState()
+
+  return postcss(tailwind(config)).process(input, {
+    from: `${path.resolve(__filename)}?test=${currentTestName}`,
+  })
+}
+
+test('PHP arrays', async () => {
+  let config = {
+    mode: 'jit',
+    purge: [
+      {
+        raw: `<h1 class="<?php echo wrap(['class' => "max-w-[16rem]"]); ?>">Hello world</h1>`,
+      },
+    ],
+    theme: {},
+    plugins: [],
+  }
+
+  let css = `@tailwind utilities`
+
+  return run(css, config).then((result) => {
+    expect(result.css).toMatchFormattedCss(`
+      .max-w-\\[16rem\\] {
+        max-width: 16rem;
+      }
+    `)
+  })
+})
+
+test('arbitrary values with quotes', async () => {
+  let config = {
+    mode: 'jit',
+    purge: [
+      {
+        raw: `<div class="content-['hello]']"></div>`,
+      },
+    ],
+    theme: {},
+    plugins: [],
+  }
+
+  let css = `@tailwind utilities`
+
+  return run(css, config).then((result) => {
+    expect(result.css).toMatchFormattedCss(`
+      .content-\\[\\'hello\\]\\'\\] {
+        content: 'hello]';
+      }
+    `)
+  })
+})