diff --git a/nanobot/agent/tools/shell.py b/nanobot/agent/tools/shell.py
index 37d16e1b..d37bb949 100644
--- a/nanobot/agent/tools/shell.py
+++ b/nanobot/agent/tools/shell.py
@@ -879,6 +879,11 @@ class ExecTool(Tool):
             if paren_depth == 0:
                 if command.startswith(("&&", "||"), i):
                     operator_len = 2
+                elif ch == "&":
+                    prev_ch = command[i - 1] if i > 0 else ""
+                    next_ch = command[i + 1] if i + 1 < len(command) else ""
+                    if prev_ch not in {"<", ">"} and next_ch != ">":
+                        operator_len = 1
                 elif ch in {";", "|"}:
                     operator_len = 1
 
diff --git a/tests/tools/test_exec_allow_patterns.py b/tests/tools/test_exec_allow_patterns.py
index 9700d29c..12a35059 100644
--- a/tests/tools/test_exec_allow_patterns.py
+++ b/tests/tools/test_exec_allow_patterns.py
@@ -67,6 +67,23 @@ def test_guard_allow_patterns_block_non_matching_chained_segment():
     assert "allowlist" in result.lower()
 
 
+def test_guard_allow_patterns_block_single_ampersand_chained_segment():
+    """A backgrounded command is also a top-level shell segment."""
+    tool = ExecTool(allow_patterns=[r"echo\s+allowlisted.*"])
+
+    result = tool._guard_command("echo allowlisted & touch /tmp/evil", "/tmp")
+    assert result is not None
+    assert "allowlist" in result.lower()
+
+
+def test_guard_allow_patterns_keep_fd_redirection_ampersand():
+    tool = ExecTool(allow_patterns=[r"echo\s+allowlisted\s+2>&1"])
+
+    result = tool._guard_command("echo allowlisted 2>&1", "/tmp")
+
+    assert result is None
+
+
 def test_deny_patterns_search_original_command_with_quoted_hash():
     """Deny checks must still inspect text after a quoted hash."""
     tool = ExecTool(deny_patterns=[r"\brm\s+-rf\s+/"])