diff --git a/autogen/beta/tools/shell/environment/base.py b/autogen/beta/tools/shell/environment/base.py
index 254c28a4884..acc7733ca91 100644
--- a/autogen/beta/tools/shell/environment/base.py
+++ b/autogen/beta/tools/shell/environment/base.py
@@ -45,6 +45,9 @@
 )
 
 
+_SHELL_OPERATORS = (">", ">>", "|", ";", "&&", "||", "`")
+
+
 def matches(pattern: str, command: str) -> bool:
     """Return True if *command* starts with *pattern* as a whole word or prefix.
 
@@ -58,6 +61,14 @@ def matches(pattern: str, command: str) -> bool:
     return rest == "" or rest[0] == " "
 
 
+def contains_shell_operator(command: str) -> bool:
+    """Return True if *command* contains shell operators that could bypass
+    the allowed-command whitelist (redirection, pipes, chaining, or
+    backtick substitution).
+    """
+    return any(op in command for op in _SHELL_OPERATORS)
+
+
 def check_ignore(command: str, workdir: Path, patterns: list[str]) -> str | None:
     """Return ``"Access denied: <path>"`` if any literal path in *command* matches *patterns*.
 
diff --git a/autogen/beta/tools/shell/environment/local.py b/autogen/beta/tools/shell/environment/local.py
index 01dba032782..c25977c2edc 100644
--- a/autogen/beta/tools/shell/environment/local.py
+++ b/autogen/beta/tools/shell/environment/local.py
@@ -9,7 +9,7 @@
 import tempfile
 from pathlib import Path
 
-from .base import READONLY_COMMANDS, ShellEnvironment, check_ignore, matches
+from .base import READONLY_COMMANDS, ShellEnvironment, check_ignore, contains_shell_operator, matches
 
 
 class LocalShellEnvironment(ShellEnvironment):
@@ -119,8 +119,11 @@ def run(self, command: str) -> str:
         Applies allowed/blocked filtering, ignore-pattern checks, then runs
         the command via :func:`subprocess.run`.
         """
-        if self._allowed is not None and not any(matches(p, command) for p in self._allowed):
-            return f"Command not allowed: {command!r}"
+        if self._allowed is not None:
+            if not any(matches(p, command) for p in self._allowed):
+                return f"Command not allowed: {command!r}"
+            if contains_shell_operator(command):
+                return f"Command not allowed (shell operators are not permitted in restricted mode): {command!r}"
 
         if self._blocked is not None and any(matches(p, command) for p in self._blocked):
             return f"Command not allowed: {command!r}"
diff --git a/test/beta/tools/test_local_shell.py b/test/beta/tools/test_local_shell.py
index dc26b308d62..14ba0f53761 100644
--- a/test/beta/tools/test_local_shell.py
+++ b/test/beta/tools/test_local_shell.py
@@ -128,13 +128,24 @@ def _make_config(self, command: str, final_reply: str = "done") -> TestConfig:
 
     @pytest.mark.asyncio
     async def test_allowed_permits_matching_command(self, tmp_path: Path) -> None:
+        output = tmp_path / "out.txt"
+        shell = LocalShellTool(environment=LocalShellEnvironment(path=tmp_path, allowed=["touch"]))
+        # "touch" is allowed and the command contains no shell operators —
+        # the file MUST be created. Mirrors test_allowed_blocks_non_matching_command,
+        # which uses the same touch pattern to assert rejection.
+        agent = Agent("a", config=self._make_config(f"touch {output}"), tools=[shell])
+        await agent.ask("run it")
+        assert output.exists(), "touch was allowed but file was not created"
+
+    @pytest.mark.asyncio
+    async def test_allowed_blocks_shell_redirect_bypass(self, tmp_path: Path) -> None:
         output = tmp_path / "out.txt"
         shell = LocalShellTool(environment=LocalShellEnvironment(path=tmp_path, allowed=["echo"]))
+        # Even though "echo" is allowed, shell redirection (`>`) must be blocked
+        # to prevent bypassing the whitelist by writing to arbitrary files.
         agent = Agent("a", config=self._make_config(f"echo hello > {output}"), tools=[shell])
         await agent.ask("run it")
-        # Command was allowed — file must exist with expected content
-        assert output.exists(), "echo was allowed but file was not created"
-        assert output.read_text().strip() == "hello"
+        assert not output.exists(), "shell redirect bypass was not blocked"
 
     @pytest.mark.asyncio
     async def test_allowed_blocks_non_matching_command(self, tmp_path: Path) -> None: