diff --git a/src/settings.py b/src/settings.py
index 5704656..acf29a9 100644
--- a/src/settings.py
+++ b/src/settings.py
@@ -97,6 +97,11 @@ DEFAULT_SETTINGS = {
     "agent_max_tool_calls": 0,
     "agent_input_token_budget": 6000,
     "agent_stream_timeout_seconds": 300,
+    # Extra directory roots that read_file / write_file may access, in
+    # addition to the built-in project data/ and system temp dirs. Each
+    # entry is an absolute path. Sensitive subpaths (.ssh, .gnupg, shell
+    # rc files, SSH key files) are always blocked regardless of roots.
+    "tool_path_extra_roots": [],
     "task_endpoint_id": "",
     "task_model": "",
     "default_endpoint_id": "",
diff --git a/src/tool_execution.py b/src/tool_execution.py
index 06d46d9..b0e8e2d 100644
--- a/src/tool_execution.py
+++ b/src/tool_execution.py
@@ -21,6 +21,143 @@ from src.tool_security import is_public_blocked_tool, owner_is_admin_or_single_u
 MAX_OUTPUT_CHARS = 10_000
 MAX_READ_CHARS = 20_000
 
+# ---------------------------------------------------------------------------
+# Path confinement for read_file / write_file
+# ---------------------------------------------------------------------------
+# read_file + write_file are admin-only tools, but the path the agent
+# supplies is model-controlled. Prompt-injection in an admin's chat can
+# weaponise "read /etc/shadow" or "write ~/.ssh/authorized_keys" without
+# the admin noticing.
+#
+# Policy:
+#   1. Sensitive-subpath deny list — checked FIRST. Blocks .ssh,
+#      .gnupg, shell rc files, token/env files even if the root above
+#      them is on the allowlist.
+#   2. Allowlist — only the directories the agent legitimately needs
+#      (project data/, system tmp). $HOME is NOT on the default list.
+#   3. Opt-in extra roots — admin can add broader roots via the
+#      "tool_path_extra_roots" setting (list of path strings).
+# ---------------------------------------------------------------------------
+
+_SENSITIVE_BASENAMES: set[str] = {
+    ".ssh", ".gnupg", ".gitconfig",
+    ".bashrc", ".bash_profile", ".bash_logout",
+    ".zshrc", ".zprofile", ".zshenv",
+    ".profile", ".tcshrc", ".cshrc",
+    ".env", ".netrc",
+}
+
+_SENSITIVE_FILE_PATTERNS: tuple[str, ...] = (
+    "authorized_keys", "id_rsa", "id_ed25519", "id_ecdsa",
+    "known_hosts",
+)
+
+
+def _is_sensitive_path(resolved: str) -> bool:
+    """Return True if *resolved* falls under a sensitive directory or
+    matches a sensitive filename — regardless of what root it sits under.
+    """
+    parts = resolved.split(os.sep)
+    filenames: set[str] = {parts[-1]} if parts else set()
+
+    # Check if any path component is a sensitive directory.
+    for part in parts:
+        if part in _SENSITIVE_BASENAMES:
+            return True
+
+    # Check filename against known sensitive files.
+    for pat in _SENSITIVE_FILE_PATTERNS:
+        if pat in filenames:
+            return True
+
+    return False
+
+
+def _tool_path_roots() -> list[str]:
+    """Return the list of directory roots that read_file / write_file
+    may touch. Default: project data/ + system temp dirs. Extra roots
+    are loaded from the ``tool_path_extra_roots`` setting.
+    """
+    roots: list[str] = []
+
+    # Project data directory — the agent's primary workspace.
+    from src.constants import DATA_DIR
+    roots.append(DATA_DIR)
+
+    # /tmp (and its macOS realpath /private/tmp).
+    roots.append("/tmp")
+    try:
+        private_tmp = os.path.realpath("/tmp")
+        if private_tmp != "/tmp":
+            roots.append(private_tmp)
+    except OSError:
+        pass
+
+    # $TMPDIR — per-user temp root on macOS (e.g. /var/folders/.../T/).
+    tmpdir = os.environ.get("TMPDIR")
+    if tmpdir:
+        roots.append(tmpdir)
+
+    # Opt-in extra roots from settings.
+    try:
+        from src.settings import get_setting
+        extra = get_setting("tool_path_extra_roots")
+        if isinstance(extra, list):
+            roots.extend(str(r) for r in extra if r)
+    except Exception:
+        pass
+
+    # Deduplicate; resolve symlinks so containment is unambiguous.
+    seen: set[str] = set()
+    out: list[str] = []
+    for r in roots:
+        try:
+            real = os.path.realpath(r)
+        except OSError:
+            continue
+        if real in seen:
+            continue
+        seen.add(real)
+        out.append(real)
+    return out
+
+
+def _resolve_tool_path(raw_path: str) -> str:
+    """Resolve and confine a model-supplied path.
+
+    Order of checks:
+      1. Non-empty path.
+      2. Sensitive-subpath deny list (blocks .ssh, .gnupg, etc.
+         even when the root is on the allowlist).
+      3. Allowlist containment (must land under one of the roots).
+
+    Returns the realpath on success. Raises ValueError on rejection.
+    Symlinks are resolved before comparison.
+    """
+    if raw_path is None or not str(raw_path).strip():
+        raise ValueError("path is required")
+    expanded = os.path.expanduser(str(raw_path).strip())
+    resolved = os.path.realpath(expanded)
+
+    if _is_sensitive_path(resolved):
+        raise ValueError(
+            f"path '{raw_path}' is inside a sensitive directory "
+            f"(e.g. .ssh, .gnupg) or matches a sensitive filename"
+        )
+
+    for root in _tool_path_roots():
+        if resolved == root:
+            return resolved
+        try:
+            common = os.path.commonpath([resolved, root])
+        except ValueError:
+            continue
+        if common == root:
+            return resolved
+    raise ValueError(
+        f"path '{raw_path}' is outside the allowed roots"
+    )
+
 # Bash + python tools used to share a single 60s timeout. That's
 # enough for one-shot commands but starves real workloads (pip
 # install, ffmpeg conversions, etc.) — and worse, the agent saw the
@@ -375,9 +512,11 @@ async def _direct_fallback(
             return {"output": output or "(no output)", "exit_code": rc or 0}
 
         if tool == "read_file":
-            path = os.path.expanduser(content.split("\n", 1)[0].strip())
-            if not path:
-                return {"error": "read_file: path required", "exit_code": 1}
+            raw_path = content.split("\n", 1)[0].strip()
+            try:
+                path = _resolve_tool_path(raw_path)
+            except ValueError as e:
+                return {"error": f"read_file: {e}", "exit_code": 1}
             try:
                 # Run blocking read in a thread to keep the loop responsive
                 def _read():
@@ -397,13 +536,14 @@ async def _direct_fallback(
 
         if tool == "write_file":
             lines = content.split("\n", 1)
-            path = os.path.expanduser(lines[0].strip())
+            raw_path = lines[0].strip()
             body = lines[1] if len(lines) > 1 else ""
-            if not path:
-                return {"error": "write_file: path required", "exit_code": 1}
+            try:
+                path = _resolve_tool_path(raw_path)
+            except ValueError as e:
+                return {"error": f"write_file: {e}", "exit_code": 1}
             try:
                 def _write():
-                    import os
                     d = os.path.dirname(path)
                     if d:
                         os.makedirs(d, exist_ok=True)
diff --git a/tests/test_tool_path_confinement.py b/tests/test_tool_path_confinement.py
new file mode 100644
index 0000000..6288623
--- /dev/null
+++ b/tests/test_tool_path_confinement.py
@@ -0,0 +1,282 @@
+"""Regression tests for read_file / write_file path confinement.
+
+Covers:
+  - /etc/shadow, /etc/passwd, /var/log — blocked (outside roots)
+  - ~/.ssh/authorized_keys — blocked (sensitive subpath deny list)
+  - Symlink that resolves into .ssh — blocked
+  - Relative traversal (~/../../etc/passwd) — blocked
+  - Shell rc files (.bashrc, .zshrc, .profile) — blocked
+  - SSH key filenames (id_rsa, id_ed25519) — blocked regardless of dir
+  - Legitimate paths under project data/ and /tmp — allowed
+  - Extra roots via tool_path_extra_roots setting — opt-in
+  - Even with $HOME as extra root, sensitive subpaths stay blocked
+"""
+
+import os
+import sys
+from types import SimpleNamespace
+from unittest.mock import patch
+
+import pytest
+
+
+def _make_block(tool_type, content):
+    return SimpleNamespace(tool_type=tool_type, content=content)
+
+
+# ── Unit tests on _is_sensitive_path ──────────────────────────────────
+
+def test_sensitive_ssh_dir():
+    from src.tool_execution import _is_sensitive_path
+    assert _is_sensitive_path("/home/user/.ssh/authorized_keys")
+    assert _is_sensitive_path(os.path.expanduser("~") + "/.ssh/config")
+
+
+def test_sensitive_gnupg_dir():
+    from src.tool_execution import _is_sensitive_path
+    assert _is_sensitive_path("/home/user/.gnupg/pubring.kbx")
+
+
+def test_sensitive_shell_rc():
+    from src.tool_execution import _is_sensitive_path
+    assert _is_sensitive_path("/home/user/.bashrc")
+    assert _is_sensitive_path("/home/user/.zshrc")
+    assert _is_sensitive_path("/home/user/.profile")
+
+
+def test_sensitive_key_filenames():
+    from src.tool_execution import _is_sensitive_path
+    assert _is_sensitive_path("/tmp/id_rsa")
+    assert _is_sensitive_path("/tmp/id_ed25519")
+    assert _is_sensitive_path("/tmp/authorized_keys")
+
+
+def test_non_sensitive_path():
+    from src.tool_execution import _is_sensitive_path
+    assert not _is_sensitive_path("/tmp/notes.txt")
+    assert not _is_sensitive_path("/home/user/projects/file.py")
+
+
+# ── Unit tests on _resolve_tool_path ─────────────────────────────────
+
+def test_blocks_etc_shadow():
+    """The motivating example: /etc/shadow must be rejected."""
+    from src.tool_execution import _resolve_tool_path
+    with pytest.raises(ValueError, match="outside the allowed roots"):
+        _resolve_tool_path("/etc/shadow")
+
+
+def test_blocks_etc_passwd():
+    from src.tool_execution import _resolve_tool_path
+    with pytest.raises(ValueError, match="outside the allowed roots"):
+        _resolve_tool_path("/etc/passwd")
+
+
+def test_blocks_var_log():
+    from src.tool_execution import _resolve_tool_path
+    with pytest.raises(ValueError, match="outside the allowed roots"):
+        _resolve_tool_path("/var/log/system.log")
+
+
+def test_blocks_ssh_authorized_keys():
+    """~/.ssh/authorized_keys — blocked by sensitive-subpath deny even
+    though $HOME is NOT a default root (the deny list fires first)."""
+    from src.tool_execution import _resolve_tool_path
+    with pytest.raises(ValueError, match="sensitive directory"):
+        _resolve_tool_path("~/.ssh/authorized_keys")
+
+
+def test_blocks_ssh_dir_absolute():
+    from src.tool_execution import _resolve_tool_path
+    home = os.path.expanduser("~")
+    with pytest.raises(ValueError, match="sensitive directory"):
+        _resolve_tool_path(os.path.join(home, ".ssh", "config"))
+
+
+def test_blocks_symlink_into_ssh(tmp_path):
+    """A symlink under /tmp that points into ~/.ssh must be caught
+    because realpath resolves the link before the deny-list check."""
+    from src.tool_execution import _resolve_tool_path
+    ssh_dir = os.path.join(os.path.expanduser("~"), ".ssh")
+    os.makedirs(ssh_dir, exist_ok=True)
+    link = tmp_path / "ssh_link"
+    try:
+        link.symlink_to(ssh_dir)
+    except OSError:
+        pytest.skip("cannot create symlink")
+    with pytest.raises(ValueError, match="sensitive directory"):
+        _resolve_tool_path(str(link))
+
+
+def test_blocks_traversal_outside_roots():
+    """~/../../etc/passwd — after tilde expansion and .. resolution the
+    path lands outside every allowed root."""
+    from src.tool_execution import _resolve_tool_path
+    with pytest.raises(ValueError):
+        _resolve_tool_path("~/../../etc/passwd")
+
+
+def test_blocks_bashrc():
+    from src.tool_execution import _resolve_tool_path
+    with pytest.raises(ValueError, match="sensitive directory"):
+        _resolve_tool_path("~/.bashrc")
+
+
+def test_blocks_zshrc():
+    from src.tool_execution import _resolve_tool_path
+    with pytest.raises(ValueError, match="sensitive directory"):
+        _resolve_tool_path("~/.zshrc")
+
+
+def test_blocks_env_file():
+    from src.tool_execution import _resolve_tool_path
+    with pytest.raises(ValueError, match="sensitive directory"):
+        _resolve_tool_path("~/.env")
+
+
+def test_blocks_netrc():
+    from src.tool_execution import _resolve_tool_path
+    with pytest.raises(ValueError, match="sensitive directory"):
+        _resolve_tool_path("~/.netrc")
+
+
+def test_allows_project_data(tmp_path):
+    """Paths under project data/ must resolve cleanly."""
+    from src.tool_execution import _resolve_tool_path
+    from src.constants import DATA_DIR
+    target = os.path.join(DATA_DIR, "test-confinement-ok.txt")
+    os.makedirs(DATA_DIR, exist_ok=True)
+    with open(target, "w") as f:
+        f.write("ok")
+    try:
+        resolved = _resolve_tool_path(target)
+        assert resolved == os.path.realpath(target)
+    finally:
+        os.unlink(target)
+
+
+def test_allows_tmp(tmp_path):
+    """Paths under /tmp (or its realpath) must resolve cleanly."""
+    from src.tool_execution import _resolve_tool_path
+    f = tmp_path / "confinement-test.txt"
+    f.write_text("ok")
+    resolved = _resolve_tool_path(str(f))
+    assert resolved == os.path.realpath(str(f))
+
+
+def test_rejects_empty_path():
+    from src.tool_execution import _resolve_tool_path
+    with pytest.raises(ValueError, match="path is required"):
+        _resolve_tool_path("")
+    with pytest.raises(ValueError, match="path is required"):
+        _resolve_tool_path("   ")
+
+
+def test_extra_roots_opt_in(tmp_path):
+    """When tool_path_extra_roots includes a directory, paths under it
+    are allowed (but sensitive subpaths are still blocked)."""
+    from src.tool_execution import _resolve_tool_path
+    extra_dir = tmp_path / "extra_root"
+    extra_dir.mkdir()
+    target = extra_dir / "file.txt"
+    target.write_text("ok")
+
+    with patch("src.settings.get_setting", return_value=[str(extra_dir)]):
+        resolved = _resolve_tool_path(str(target))
+        assert resolved == os.path.realpath(str(target))
+
+
+def test_extra_root_still_blocks_sensitive(tmp_path):
+    """Even when $HOME is in tool_path_extra_roots, ~/.ssh/authorized_keys
+    must still be rejected by the sensitive-subpath deny list."""
+    from src.tool_execution import _resolve_tool_path
+    home = os.path.expanduser("~")
+    with patch("src.settings.get_setting", return_value=[home]):
+        with pytest.raises(ValueError, match="sensitive directory"):
+            _resolve_tool_path("~/.ssh/authorized_keys")
+
+
+# ── Integration: dispatch-level tests ────────────────────────────────
+
+@pytest.mark.asyncio
+async def test_read_file_dispatch_blocks_etc_shadow(monkeypatch):
+    """End-to-end: read_file dispatch must reject /etc/shadow."""
+    auth_mod = sys.modules.get("core.auth")
+    if auth_mod is None:
+        import core.auth as _real_auth
+        auth_mod = _real_auth
+
+    class _AdminAuth:
+        is_configured = True
+        def is_admin(self, username):
+            return True
+
+    monkeypatch.setattr(auth_mod, "AuthManager", lambda: _AdminAuth())
+    monkeypatch.setattr(
+        "src.tool_execution.owner_is_admin_or_single_user",
+        lambda owner: True,
+    )
+
+    from src.tool_execution import execute_tool_block
+    desc, result = await execute_tool_block(
+        _make_block("read_file", "/etc/shadow"),
+        owner="admin-user",
+    )
+    assert "outside the allowed roots" in (result.get("error") or "")
+    assert result.get("exit_code") == 1
+
+
+@pytest.mark.asyncio
+async def test_write_file_dispatch_blocks_authorized_keys(monkeypatch):
+    """End-to-end: write_file dispatch must reject ~/.ssh/authorized_keys."""
+    auth_mod = sys.modules.get("core.auth")
+    if auth_mod is None:
+        import core.auth as _real_auth
+        auth_mod = _real_auth
+
+    class _AdminAuth:
+        is_configured = True
+        def is_admin(self, username):
+            return True
+
+    monkeypatch.setattr(auth_mod, "AuthManager", lambda: _AdminAuth())
+    monkeypatch.setattr(
+        "src.tool_execution.owner_is_admin_or_single_user",
+        lambda owner: True,
+    )
+
+    from src.tool_execution import execute_tool_block
+    desc, result = await execute_tool_block(
+        _make_block("write_file", "~/.ssh/authorized_keys\nssh-rsa AAAAB3..."),
+        owner="admin-user",
+    )
+    assert "sensitive directory" in (result.get("error") or "")
+    assert result.get("exit_code") == 1
+
+
+@pytest.mark.asyncio
+async def test_write_file_dispatch_blocks_cron(monkeypatch):
+    """End-to-end: write_file to /etc/cron.d must be rejected."""
+    auth_mod = sys.modules.get("core.auth")
+    if auth_mod is None:
+        import core.auth as _real_auth
+        auth_mod = _real_auth
+
+    class _AdminAuth:
+        is_configured = True
+        def is_admin(self, username):
+            return True
+
+    monkeypatch.setattr(auth_mod, "AuthManager", lambda: _AdminAuth())
+    monkeypatch.setattr(
+        "src.tool_execution.owner_is_admin_or_single_user",
+        lambda owner: True,
+    )
+
+    from src.tool_execution import execute_tool_block
+    desc, result = await execute_tool_block(
+        _make_block("write_file", "/etc/cron.d/agent-payload\n* * * * * root /tmp/p\n"),
+        owner="admin-user",
+    )
+    assert "outside the allowed roots" in (result.get("error") or "")
+    assert result.get("exit_code") == 1