diff --git a/tests/tools/test_syntax_preflight.py b/tests/tools/test_syntax_preflight.py
new file mode 100644
index 000000000..488c36976
--- /dev/null
+++ b/tests/tools/test_syntax_preflight.py
@@ -0,0 +1,107 @@
+"""Tests for syntax preflight check in execute_code (issue #312)."""
+
+import ast
+import json
+import pytest
+
+
+class TestSyntaxPreflight:
+    """Verify that execute_code catches syntax errors before sandbox execution."""
+
+    def test_valid_syntax_passes_parse(self):
+        """Valid Python should pass ast.parse."""
+        code = "print('hello')\nx = 1 + 2\n"
+        ast.parse(code)  # should not raise
+
+    def test_syntax_error_indentation(self):
+        """IndentationError is a subclass of SyntaxError."""
+        code = "def foo():\nbar()\n"
+        with pytest.raises(SyntaxError):
+            ast.parse(code)
+
+    def test_syntax_error_missing_colon(self):
+        code = "if True\n  pass\n"
+        with pytest.raises(SyntaxError):
+            ast.parse(code)
+
+    def test_syntax_error_unmatched_paren(self):
+        code = "x = (1 + 2\n"
+        with pytest.raises(SyntaxError):
+            ast.parse(code)
+
+    def test_syntax_error_invalid_token(self):
+        code = "x = 1 +*\n"
+        with pytest.raises(SyntaxError):
+            ast.parse(code)
+
+    def test_syntax_error_details(self):
+        """SyntaxError should provide line, offset, msg."""
+        code = "if True\n  pass\n"
+        with pytest.raises(SyntaxError) as exc_info:
+            ast.parse(code)
+        e = exc_info.value
+        assert e.lineno is not None
+        assert e.msg is not None
+
+    def test_empty_string_passes(self):
+        """Empty string is valid Python (empty module)."""
+        ast.parse("")
+
+    def test_comments_only_passes(self):
+        ast.parse("# just a comment\n# another\n")
+
+    def test_complex_valid_code(self):
+        code = '''
+import os
+def foo(x):
+    if x > 0:
+        return x * 2
+    return 0
+
+result = [foo(i) for i in range(10)]
+print(result)
+'''
+        ast.parse(code)
+
+
+class TestSyntaxPreflightResponse:
+    """Test the error response format from the preflight check."""
+
+    def _check_syntax(self, code):
+        """Mimic the preflight check logic from execute_code."""
+        try:
+            ast.parse(code)
+            return None
+        except SyntaxError as e:
+            return json.dumps({
+                "error": f"Python syntax error: {e.msg}",
+                "line": e.lineno,
+                "offset": e.offset,
+                "text": (e.text or "").strip()[:200],
+            })
+
+    def test_returns_json_error(self):
+        result = self._check_syntax("if True\n  pass\n")
+        assert result is not None
+        data = json.loads(result)
+        assert "error" in data
+        assert "syntax error" in data["error"].lower()
+
+    def test_includes_line_number(self):
+        result = self._check_syntax("x = 1\nif True\n  pass\n")
+        data = json.loads(result)
+        assert data["line"] == 2  # error on line 2
+
+    def test_includes_offset(self):
+        result = self._check_syntax("x = (1 + 2\n")
+        data = json.loads(result)
+        assert data["offset"] is not None
+
+    def test_includes_snippet(self):
+        result = self._check_syntax("if True\n")
+        data = json.loads(result)
+        assert "if True" in data["text"]
+
+    def test_none_for_valid_code(self):
+        result = self._check_syntax("print('ok')")
+        assert result is None
diff --git a/tools/code_execution_tool.py b/tools/code_execution_tool.py
index 8dd6c759e..aa17e58a1 100644
--- a/tools/code_execution_tool.py
+++ b/tools/code_execution_tool.py
@@ -28,6 +28,7 @@ Platform: Linux / macOS only (Unix domain sockets for local). Disabled on Window
 Remote execution additionally requires Python 3 in the terminal backend.
 """
 
+import ast
 import base64
 import json
 import logging
@@ -893,6 +894,20 @@ def execute_code(
     if not code or not code.strip():
         return json.dumps({"error": "No code provided."})
 
+    # Poka-yoke (#312): Syntax check before execution.
+    # 83.2% of execute_code errors are Python exceptions; most are syntax
+    # errors the LLM generated.  ast.parse() is sub-millisecond and catches
+    # them before we spin up a sandbox child process.
+    try:
+        ast.parse(code)
+    except SyntaxError as e:
+        return json.dumps({
+            "error": f"Python syntax error: {e.msg}",
+            "line": e.lineno,
+            "offset": e.offset,
+            "text": (e.text or "").strip()[:200],
+        })
+
     # Dispatch: remote backends use file-based RPC, local uses UDS
     from tools.terminal_tool import _get_env_config
     env_type = _get_env_config()["env_type"]