diff --git a/frontend/src/lib/utils/content-parser.test.ts b/frontend/src/lib/utils/content-parser.test.ts
index 85b715e5d..10517158d 100644
--- a/frontend/src/lib/utils/content-parser.test.ts
+++ b/frontend/src/lib/utils/content-parser.test.ts
@@ -81,7 +81,7 @@ describe("parseContent", () => {
 
   it("preserves leading whitespace in tail text", () => {
     const segments =
-      parseContent("```code\ncontent```\n  Trailing text");
+      parseContent("```code\ncontent\n```\n  Trailing text");
     expect(segments).toHaveLength(2);
     expect(segments[0]).toMatchObject({ type: "code" });
     expect(segments[1]).toEqual({
@@ -111,6 +111,38 @@ describe("parseContent", () => {
     ]);
   });
 
+  it("keeps nested shorter fences inside longer code blocks", () => {
+    const content =
+      "````markdown\nSome context paragraph.\n\n```qmd\nauthor: \"Jane Doe\"\n```\n\nMore context here.\n````";
+    const segments = parseContent(content);
+    expect(segments).toEqual([
+      {
+        type: "code",
+        content:
+          "Some context paragraph.\n\n```qmd\nauthor: \"Jane Doe\"\n```\n\nMore context here.\n",
+        label: "markdown",
+      },
+    ]);
+  });
+
+  it("keeps inline same-length backtick runs inside code blocks", () => {
+    const content =
+      "```javascript\nconst fence = \"```\";\n[Thinking]\nnot parsed\n```\nAfter";
+    const segments = parseContent(content);
+    expect(segments).toEqual([
+      {
+        type: "code",
+        content:
+          "const fence = \"```\";\n[Thinking]\nnot parsed\n",
+        label: "javascript",
+      },
+      {
+        type: "text",
+        content: "\nAfter",
+      },
+    ]);
+  });
+
   it("omits label for code blocks without language", () => {
     const segments = parseContent("```\nplain code\n```");
     expect(segments[0]).toEqual({
diff --git a/frontend/src/lib/utils/content-parser.ts b/frontend/src/lib/utils/content-parser.ts
index 96f02b46e..c122477d9 100644
--- a/frontend/src/lib/utils/content-parser.ts
+++ b/frontend/src/lib/utils/content-parser.ts
@@ -70,8 +70,6 @@ const TOOL_RE = new RegExp(
   "g",
 );
 
-const CODE_BLOCK_RE = /```(\w*)\n([\s\S]*?)```/g;
-
 /** Returns true if text[from..to) contains a backtick run of
  *  exactly `len` characters. Used to detect a closing inline
  *  code delimiter on the same line as the opener. */
@@ -95,7 +93,7 @@ function hasRunBefore(
  * backtick run of length N is closed by the next run of exactly
  * N backticks. Fenced code blocks (triple-backtick at line
  * start followed by a newline) are excluded — those are handled
- * separately by CODE_BLOCK_RE.
+ * separately by codeBlockMatches.
  */
 function scanInlineCodeSpans(
   text: string,
@@ -125,7 +123,6 @@ function scanInlineCodeSpans(
     }
 
     // Scan for a closing run of exactly the same length.
-    let found = false;
     for (let j = i; j < text.length; j++) {
       if (text[j] !== "`") continue;
       const closeStart = j;
@@ -133,7 +130,6 @@ function scanInlineCodeSpans(
       if (j - closeStart === runLen) {
         spans.push([openStart, j]);
         i = j;
-        found = true;
         break;
       }
     }
@@ -190,6 +186,92 @@ function insideInlineCode(
   return spans.some(([s, e]) => pos > s && pos < e);
 }
 
+function atFenceLineStart(text: string, pos: number): boolean {
+  const lineStart = text.lastIndexOf("\n", pos - 1) + 1;
+  return /^[ \t]{0,3}$/.test(text.slice(lineStart, pos));
+}
+
+function countBackticks(text: string, pos: number): number {
+  let end = pos;
+  while (end < text.length && text[end] === "`") end++;
+  return end - pos;
+}
+
+function closingFence(
+  text: string,
+  contentStart: number,
+  fenceLen: number,
+): { contentEnd: number; end: number } | undefined {
+  let pos = contentStart;
+  while (pos < text.length) {
+    const tickStart = text.indexOf("`", pos);
+    if (tickStart < 0) return undefined;
+    const lineStart = text.lastIndexOf("\n", tickStart - 1) + 1;
+    const nextLineStart = text.indexOf("\n", tickStart);
+    const lineEnd =
+      nextLineStart >= 0 ? nextLineStart : text.length;
+
+    const tickCount = countBackticks(text, tickStart);
+    const rest = text.slice(tickStart + tickCount, lineEnd);
+    if (
+      tickCount >= fenceLen &&
+      atFenceLineStart(text, tickStart) &&
+      /^[ \t]*$/.test(rest)
+    ) {
+      return { contentEnd: lineStart, end: lineEnd };
+    }
+
+    pos = tickStart + tickCount;
+  }
+  return undefined;
+}
+
+function codeBlockMatches(text: string): Match[] {
+  const matches: Match[] = [];
+  let pos = 0;
+
+  while (pos < text.length) {
+    const start = text.indexOf("```", pos);
+    if (start < 0) break;
+
+    if (!atFenceLineStart(text, start)) {
+      pos = start + 1;
+      continue;
+    }
+
+    const fenceLen = countBackticks(text, start);
+    const infoStart = start + fenceLen;
+    const lineEnd = text.indexOf("\n", infoStart);
+    if (lineEnd < 0) break;
+
+    const info = text.slice(infoStart, lineEnd);
+    if (info.includes("`")) {
+      pos = infoStart;
+      continue;
+    }
+
+    const contentStart = lineEnd + 1;
+    const close = closingFence(text, contentStart, fenceLen);
+    if (close === undefined) {
+      pos = infoStart;
+      continue;
+    }
+
+    matches.push({
+      start,
+      end: close.end,
+      segment: {
+        type: "code",
+        content: text.slice(contentStart, close.contentEnd),
+        label: info.trim() || undefined,
+      },
+    });
+    pos = close.end;
+  }
+
+  return matches;
+}
+
 function extractMatches(text: string, parseTools = true): Match[] {
   const matches: Match[] = [];
 
@@ -271,22 +353,14 @@ function extractMatches(text: string, parseTools = true): Match[] {
     }
   }
 
-  for (const m of text.matchAll(CODE_BLOCK_RE)) {
-    const idx = m.index!;
+  for (const m of codeBlockMatches(text)) {
+    const idx = m.start;
     const insideOther = matches.some(
       (o) => idx >= o.start && idx < o.end,
     );
     if (insideOther) continue;
 
-    matches.push({
-      start: idx,
-      end: idx + m[0].length,
-      segment: {
-        type: "code",
-        content: m[2] ?? "",
-        label: m[1] || undefined,
-      },
-    });
+    matches.push(m);
   }
 
   return matches;