From ae4c95fe719ce7edb4ecbb21eecbe002aab3534d Mon Sep 17 00:00:00 2001
From: Sharath Kumar <7642133+builtbysharath@users.noreply.github.com>
Date: Sun, 11 Oct 2026 22:34:13 +0530
Subject: [PATCH] Fix container fence when content has a line of colons

---
 lib/index.js | 39 +++++++++++++++++++++--
 test.js      | 90 ++++++++++++++++++++++++++++++++++++++++++++++++++++
 2 files changed, 127 insertions(+), 2 deletions(-)

diff --git a/lib/index.js b/lib/index.js
index 6008625..435c7d7 100644
--- a/lib/index.js
+++ b/lib/index.js
@@ -146,7 +146,7 @@ export function directiveToMarkdown(options) {
    */
   function handleDirective(node, _, state, info) {
     const tracker = state.createTracker(info)
-    const sequence = fence(node)
+    let sequence = fence(node)
     const exit = state.enter(node.type)
     let value = tracker.move(sequence + (node.name || ''))
     const attributesValue = attributes(node, state)
@@ -200,7 +200,19 @@ export function directiveToMarkdown(options) {
 
       if (shallow && shallow.children && shallow.children.length > 0) {
         value += tracker.move('\n')
-        value += tracker.move(state.containerFlow(shallow, tracker.current()))
+        const content = state.containerFlow(shallow, tracker.current())
+        value += tracker.move(content)
+
+        // A line in the content of colons with only spaces and tabs around them
+        // (such as `:::` in code) closes the container if it has as many colons
+        // as the fence, so make the fence longer.
+        const size = longestColonLine(content) + 1
+
+        if (size > sequence.length) {
+          const extra = ':'.repeat(size - sequence.length)
+          value = extra + value
+          sequence += extra
+        }
       }
 
       value += tracker.move('\n' + sequence)
@@ -560,6 +572,29 @@ function inlineDirectiveLabel(node) {
   )
 }
 
+/**
+ * Get the size of the longest sequence of colons on a line with only spaces
+ * and tabs around it.
+ *
+ * @param {string} value
+ *   Serialized markdown.
+ * @returns {number}
+ *   Size of the longest sequence, `0` if there are none.
+ */
+function longestColonLine(value) {
+  const expression = /^[\t ]*:+[\t ]*$/gm
+  let size = 0
+  /** @type {RegExpExecArray | null} */
+  let match
+
+  while ((match = expression.exec(value))) {
+    const count = ccount(match[0], ':')
+    if (count > size) size = count
+  }
+
+  return size
+}
+
 /**
  * Determine the fence size for a directive node.
  *
diff --git a/test.js b/test.js
index 6ae75ea..dc4635d 100644
--- a/test.js
+++ b/test.js
@@ -1051,6 +1051,96 @@ test('directiveToMarkdown()', async function (t) {
     }
   )
 
+  await t.test(
+    'should serialize containers w/ more colons than a line of colons in code',
+    async function () {
+      assert.equal(
+        toMarkdown(
+          {
+            type: 'containerDirective',
+            name: 'a',
+            children: [{type: 'code', value: 'b\n:::\nc'}]
+          },
+          {extensions: [directiveToMarkdown()]}
+        ),
+        '::::a\n```\nb\n:::\nc\n```\n::::\n'
+      )
+    }
+  )
+
+  await t.test(
+    'should serialize containers w/ more colons than a line of colons, spaces, and tabs',
+    async function () {
+      assert.equal(
+        toMarkdown(
+          {
+            type: 'containerDirective',
+            name: 'a',
+            children: [{type: 'code', value: ' \t::::: '}]
+          },
+          {extensions: [directiveToMarkdown()]}
+        ),
+        '::::::a\n```\n \t::::: \n```\n::::::\n'
+      )
+    }
+  )
+
+  await t.test(
+    'should not serialize containers w/ more colons for a line w/ colons and other characters',
+    async function () {
+      assert.equal(
+        toMarkdown(
+          {
+            type: 'containerDirective',
+            name: 'a',
+            children: [{type: 'code', value: ':::b\n::: c'}]
+          },
+          {extensions: [directiveToMarkdown()]}
+        ),
+        ':::a\n```\n:::b\n::: c\n```\n:::\n'
+      )
+    }
+  )
+
+  await t.test(
+    'should serialize outer containers w/ more colons than inner containers that have code',
+    async function () {
+      assert.equal(
+        toMarkdown(
+          {
+            type: 'containerDirective',
+            name: 'a',
+            children: [
+              {
+                type: 'containerDirective',
+                name: 'b',
+                children: [{type: 'code', value: ':::'}]
+              }
+            ]
+          },
+          {extensions: [directiveToMarkdown()]}
+        ),
+        ':::::a\n::::b\n```\n:::\n```\n::::\n:::::\n'
+      )
+    }
+  )
+
+  await t.test(
+    'should roundtrip a container w/ a directive in code',
+    async function () {
+      const value = '::::a\n```markdown\n:::b\nc\n:::\n```\n::::\n'
+      const tree = fromMarkdown(value, {
+        extensions: [directive()],
+        mdastExtensions: [directiveFromMarkdown()]
+      })
+
+      assert.equal(
+        toMarkdown(tree, {extensions: [directiveToMarkdown()]}),
+        value
+      )
+    }
+  )
+
   await t.test(
     'should escape a `:` in phrasing when followed by an alpha',
     async function () {