diff --git a/nanobot/utils/helpers.py b/nanobot/utils/helpers.py
index 6341bc2bc..181cea9ca 100644
--- a/nanobot/utils/helpers.py
+++ b/nanobot/utils/helpers.py
@@ -368,6 +368,22 @@ def maybe_persist_tool_result(
     )
 
 
+def _fence_line(content: str, fence_pos: int) -> str:
+    line_end = content.find("\n", fence_pos)
+    if line_end < 0:
+        return content[fence_pos:]
+    return content[fence_pos:line_end]
+
+
+def _split_inside_fenced_code_block(content: str, pos: int) -> tuple[bool, int, str]:
+    if content[:pos].count("```") % 2 == 0:
+        return False, -1, ""
+    opening = content.rfind("```", 0, pos)
+    if opening < 0:
+        return True, -1, "```"
+    return True, opening, _fence_line(content, opening)
+
+
 def split_message(content: str, max_len: int = 2000) -> list[str]:
     """
     Split content into chunks within max_len, preferring line breaks.
@@ -395,6 +411,36 @@ def split_message(content: str, max_len: int = 2000) -> list[str]:
             pos = cut.rfind(" ")
         if pos <= 0:
             pos = max_len
+        inside_code, opening, fence = _split_inside_fenced_code_block(content, pos)
+        if inside_code:
+            if opening > 0:
+                pos = opening
+            else:
+                closing = "\n```"
+                min_code_pos = len(fence)
+                if content.startswith(fence + "\n"):
+                    min_code_pos += 1
+                if pos < min_code_pos and min_code_pos + len(closing) > max_len:
+                    chunks.append(content[:max_len])
+                    content = content[max_len:].lstrip()
+                    continue
+                if pos + len(closing) > max_len:
+                    budget = max_len - len(closing)
+                    if budget > 0:
+                        recut = content[:budget]
+                        adjusted = recut.rfind("\n")
+                        if adjusted <= 0:
+                            adjusted = recut.rfind(" ")
+                        pos = adjusted if adjusted > 0 else budget
+                    else:
+                        closing = "```"
+                        pos = max_len - len(closing)
+                chunks.append(content[:pos] + closing)
+                remainder = content[pos:]
+                if remainder.startswith("\n"):
+                    remainder = remainder[1:]
+                content = f"{fence}\n{remainder}"
+                continue
         chunks.append(content[:pos])
         content = content[pos:].lstrip()
     return chunks
diff --git a/tests/utils/test_helpers.py b/tests/utils/test_helpers.py
new file mode 100644
index 000000000..1823c9b34
--- /dev/null
+++ b/tests/utils/test_helpers.py
@@ -0,0 +1,60 @@
+from nanobot.utils.helpers import split_message
+
+
+def test_split_message_no_code_blocks_unchanged():
+    content = "alpha beta gamma delta"
+
+    assert split_message(content, max_len=12) == ["alpha beta", "gamma delta"]
+
+
+def test_split_message_outside_code_block_unchanged():
+    content = "alpha beta gamma delta\n```python\nx = 1\n```\ndone"
+
+    chunks = split_message(content, max_len=12)
+
+    assert chunks[0] == "alpha beta"
+    assert chunks[1].startswith("gamma")
+
+
+def test_split_message_inside_code_block_moves_before_fence():
+    content = "Intro paragraph.\n```python\nprint('a')\nprint('b')\n```\nDone"
+
+    chunks = split_message(content, max_len=35)
+
+    assert chunks[0] == "Intro paragraph.\n"
+    assert chunks[1].startswith("```python\nprint('a')")
+    assert all(chunk.count("```") % 2 == 0 for chunk in chunks[1:])
+
+
+def test_split_message_code_block_longer_than_max_len_closes_and_reopens():
+    content = "```python\n" + ("print('line one')\n" * 6) + "```\nDone"
+
+    chunks = split_message(content, max_len=60)
+
+    assert len(chunks) > 1
+    assert all(len(chunk) <= 60 for chunk in chunks)
+    assert all(chunk.count("```") % 2 == 0 for chunk in chunks)
+    assert chunks[0].startswith("```python\n")
+    assert chunks[0].endswith("\n```")
+    assert chunks[1].startswith("```python\n")
+
+
+def test_split_message_multiple_code_blocks_moves_second_block_to_next_chunk():
+    content = (
+        "First\n"
+        "```js\n"
+        "one();\n"
+        "```\n"
+        "Middle paragraph here\n"
+        "```py\n"
+        "two()\n"
+        "three()\n"
+        "```\n"
+        "End"
+    )
+
+    chunks = split_message(content, max_len=55)
+
+    assert chunks[0].endswith("Middle paragraph here\n")
+    assert chunks[1].startswith("```py\n")
+    assert all(chunk.count("```") % 2 == 0 for chunk in chunks)