diff --git a/headroom/cli/wrap.py b/headroom/cli/wrap.py
index 17ee01d76..863a777ef 100644
--- a/headroom/cli/wrap.py
+++ b/headroom/cli/wrap.py
@@ -263,6 +263,19 @@ def _print_telemetry_notice() -> None:
         click.echo(notice)
 
 
+def _prepend_rtk_bin_to_path(env: dict[str, str]) -> None:
+    """Ensure wrapped shells can resolve Headroom-managed `rtk`."""
+
+    from headroom.rtk import RTK_BIN_DIR
+
+    rtk_bin = str(RTK_BIN_DIR)
+    path_key = next((key for key in env if key.lower() == "path"), "PATH")
+    current_path = env.get(path_key, "")
+    path_entries = current_path.split(os.pathsep) if current_path else []
+    if rtk_bin not in path_entries:
+        env[path_key] = f"{rtk_bin}{os.pathsep}{current_path}" if current_path else rtk_bin
+
+
 # Proxy health check (reused from evals/suite_runner.py pattern)
 
 
@@ -2498,6 +2511,7 @@ def _launch_tool(
     signal.signal(signal.SIGTERM, cleanup)
 
     try:
+        _prepend_rtk_bin_to_path(env)
         click.echo()
         padded = f"HEADROOM WRAP: {tool_label}".center(47)
         click.echo("  ╔═══════════════════════════════════════════════╗")
diff --git a/tests/test_cli/test_wrap_helpers.py b/tests/test_cli/test_wrap_helpers.py
index 81cf1cf50..4d86dda7d 100644
--- a/tests/test_cli/test_wrap_helpers.py
+++ b/tests/test_cli/test_wrap_helpers.py
@@ -93,6 +93,46 @@ def test_print_wrap_banner_title_is_centered_or_near_centered() -> None:
     )
 
 
+def test_prepend_rtk_bin_to_path_injects_managed_bin_dir(monkeypatch: pytest.MonkeyPatch) -> None:
+    managed_dir = Path("/tmp/headroom-bin")
+    monkeypatch.setattr("headroom.rtk.RTK_BIN_DIR", managed_dir)
+
+    env = {"PATH": "/usr/bin:/bin"}
+
+    wrap_mod._prepend_rtk_bin_to_path(env)
+
+    assert env["PATH"].split(os.pathsep)[0] == str(managed_dir)
+    assert "/usr/bin" in env["PATH"]
+
+
+def test_prepend_rtk_bin_to_path_updates_windows_style_path_key(
+    monkeypatch: pytest.MonkeyPatch,
+) -> None:
+    managed_dir = Path("/tmp/headroom-bin")
+    monkeypatch.setattr("headroom.rtk.RTK_BIN_DIR", managed_dir)
+
+    env = {"Path": "C:\\Windows\\System32"}
+
+    wrap_mod._prepend_rtk_bin_to_path(env)
+
+    assert env["Path"].split(os.pathsep)[0] == str(managed_dir)
+    assert "PATH" not in env
+
+
+def test_prepend_rtk_bin_to_path_does_not_duplicate_windows_style_path_key(
+    monkeypatch: pytest.MonkeyPatch,
+) -> None:
+    managed_dir = Path("/tmp/headroom-bin")
+    monkeypatch.setattr("headroom.rtk.RTK_BIN_DIR", managed_dir)
+
+    env = {"Path": f"{managed_dir}{os.pathsep}C:\\Windows\\System32"}
+
+    wrap_mod._prepend_rtk_bin_to_path(env)
+
+    assert env["Path"] == f"{managed_dir}{os.pathsep}C:\\Windows\\System32"
+    assert env["Path"].split(os.pathsep).count(str(managed_dir)) == 1
+
+
 # ---------------------------------------------------------------------------
 # _setup_context_tool_for_agent — all five branches:
 #   1. lean-ctx mode → calls _setup_lean_ctx_agent, returns None