diff --git a/src/plyngent/tools/file/fs_ops.py b/src/plyngent/tools/file/fs_ops.py
index 78c23d6..98b6495 100644
--- a/src/plyngent/tools/file/fs_ops.py
+++ b/src/plyngent/tools/file/fs_ops.py
@@ -4,6 +4,7 @@ import shutil
 from pathlib import Path
 
 from plyngent.agent import ToolTag, invalidate_lineno_read, tool
+from plyngent.tools.trash import move_to_trash, under_system_temp
 from plyngent.tools.workspace import AccessMode, WorkspaceError, get_workspace_root, resolve_path
 
 
@@ -124,37 +125,46 @@ async def move_path(src: str, dst: str, *, overwrite: bool = False) -> str:
     return _copy_or_move_validated(source, dest, root, src=src, dst=dst, overwrite=overwrite, action="move")
 
 
-def _delete_directory(target: Path, path: str, *, recursive: bool) -> str:
-    if recursive:
-        shutil.rmtree(target)
+def _discard(target: Path, path: str, *, kind: str, permanent: bool, detail: str = "") -> str:
+    """Move *target* to the system trash (default), or delete it for good."""
+    if permanent:
+        _remove_existing(target)
         invalidate_lineno_read(str(target))
-        return f"deleted directory {path} (recursive)"
-    try:
-        _ = next(target.iterdir())
-    except StopIteration:
-        target.rmdir()
-        invalidate_lineno_read(str(target))
-        return f"deleted empty directory {path}"
-    return f"error: directory not empty: {path} (set recursive=true)"
+        return f"deleted {kind} {path}{detail}"
+    error = move_to_trash(target)
+    if error is not None:
+        return error
+    invalidate_lineno_read(str(target))
+    return f"deleted {kind} {path} (moved to system trash)"
 
 
-def _delete_target(target: Path, path: str, *, recursive: bool) -> str:
+def _delete_target(target: Path, path: str, *, recursive: bool, permanent: bool) -> str:
+    if target.is_dir() and not target.is_symlink():
+        if recursive:
+            return _discard(target, path, kind="directory", permanent=permanent, detail=" (recursive)")
+        try:
+            _ = next(target.iterdir())
+        except StopIteration:
+            return _discard(target, path, kind="empty directory", permanent=permanent)
+        return f"error: directory not empty: {path} (set recursive=true)"
     if target.is_symlink() or target.is_file():
-        kind = _kind(target)
-        target.unlink()
-        invalidate_lineno_read(str(target))
-        return f"deleted {kind} {path}"
-    if target.is_dir():
-        return _delete_directory(target, path, recursive=recursive)
+        return _discard(target, path, kind=_kind(target), permanent=permanent)
     return f"error: unsupported path type: {path}"
 
 
 @tool(tags=ToolTag.LOCAL | ToolTag.INSTANCE_STATE | ToolTag.YOLO, writes=("path",))
-async def delete_path(path: str, *, recursive: bool = False) -> str:
+async def delete_path(path: str, *, recursive: bool = False, permanent: bool = False) -> str:
     """Delete a file or directory under the workspace.
 
-    Files and empty directories are removed always. Non-empty directories require
-    ``recursive=true`` (uses ``shutil.rmtree``). The workspace root cannot be deleted.
+    The path goes to the system trash (the desktop's own trash / Recycle Bin), so
+    a deletion can be undone there; ``permanent=true`` removes it for good
+    instead. Files and empty directories are removed always, while non-empty
+    directories require ``recursive=true`` (uses ``shutil.rmtree``). The
+    workspace root cannot be deleted. When the trash is unavailable for this
+    path, nothing is deleted and the error says how to delete on purpose.
+
+    Paths under the OS temporary directory are deleted for good either way: they
+    are scratch space, not something to restore.
     """
     try:
         target = resolve_path(path, required=AccessMode.WRITE)
@@ -167,6 +177,11 @@ async def delete_path(path: str, *, recursive: bool = False) -> str:
     if target == root:
         return "error: cannot delete the workspace root"
     try:
-        return _delete_target(target, path, recursive=recursive)
+        return _delete_target(
+            target,
+            path,
+            recursive=recursive,
+            permanent=permanent or under_system_temp(target),
+        )
     except OSError as exc:
         return f"error: delete failed: {exc}"
diff --git a/src/plyngent/tools/temp_workspace.py b/src/plyngent/tools/temp_workspace.py
index 7d6fd47..0ca016d 100644
--- a/src/plyngent/tools/temp_workspace.py
+++ b/src/plyngent/tools/temp_workspace.py
@@ -6,6 +6,7 @@ import tempfile
 from pathlib import Path
 
 from plyngent.agent import ToolTag, tool
+from plyngent.tools.trash import under_system_temp
 from plyngent.tools.workspace import (
     MAX_TEMPORARY_WORKSPACES,
     WorkspaceError,
@@ -32,22 +33,14 @@ def _sanitize_prefix(prefix: str) -> str:
     return cleaned
 
 
-def _is_under_system_temp(path: Path) -> bool:
-    """True if *path* is under the OS temporary directory (safe to rmtree)."""
-    try:
-        temp_root = Path(tempfile.gettempdir()).expanduser().resolve()
-        resolved = path.expanduser().resolve()
-        _ = resolved.relative_to(temp_root)
-    except OSError, ValueError:
-        return False
-    return True
-
-
 def cleanup_temporary_workspaces() -> int:
     """Remove directories created by :func:`new_temporary_workspace` (chat exit).
 
     Only deletes paths still under the system temp dir. Returns the number of
     directories removed. No-op when no instance is bound.
+
+    These are scratch directories, so they are removed for good rather than
+    moved to the trash the delete tool would use.
     """
     from plyngent.tools.context import get_instance
 
@@ -55,7 +48,7 @@ def cleanup_temporary_workspaces() -> int:
         return 0
     removed = 0
     for path in pop_owned_temporary_workspaces():
-        if not _is_under_system_temp(path):
+        if not under_system_temp(path):
             remove_workspace_allowlist(path)
             continue
         if path.is_dir():
diff --git a/src/plyngent/tools/trash.py b/src/plyngent/tools/trash.py
new file mode 100644
index 0000000..210a03a
--- /dev/null
+++ b/src/plyngent/tools/trash.py
@@ -0,0 +1,61 @@
+"""Move a path to the system trash instead of destroying it.
+
+``delete_path`` hands every removal to :func:`move_to_trash`, so a delete the
+human approved (or YOLO skipped) can still be undone from the desktop's own
+trash. The platform work is ``send2trash``: the freedesktop trash specification
+on Linux, the Finder trash on macOS, the Recycle Bin on Windows.
+
+Scratch paths under the OS temporary directory are the exception — they are
+deleted for good, since nobody restores them and a trash on the ``/tmp`` volume
+would only collect them (see :func:`under_system_temp`).
+"""
+
+from __future__ import annotations
+
+import tempfile
+from pathlib import Path
+
+
+def is_available() -> bool:
+    """True when ``send2trash`` can be imported.
+
+    It is a required dependency, so ``False`` means a broken install rather than
+    an expected absence; the delete path then reports the problem instead of
+    destroying the file.
+    """
+    from importlib.util import find_spec
+
+    return find_spec("send2trash") is not None
+
+
+def under_system_temp(path: Path) -> bool:
+    """True if *path* is under the OS temporary directory (scratch space)."""
+    try:
+        temp_root = Path(tempfile.gettempdir()).expanduser().resolve()
+        resolved = path.expanduser().resolve()
+        _ = resolved.relative_to(temp_root)
+    except OSError, ValueError:
+        return False
+    return True
+
+
+def move_to_trash(path: Path) -> str | None:
+    """Send *path* to the system trash; return an error text, or ``None`` on success.
+
+    A failure is always reported, never downgraded to a permanent delete: the
+    human was told the path is recoverable, so a trash that is unavailable for
+    this path leaves the file untouched and says how to remove it on purpose.
+    """
+    if not is_available():
+        return "error: cannot move to trash: send2trash is not installed (use permanent=true)"
+
+    from send2trash import TrashPermissionError, send2trash
+
+    try:
+        send2trash(str(path))
+    except TrashPermissionError as exc:
+        # A volume with no trash directory and no permission to create one.
+        return f"error: cannot move to trash: {exc} (use permanent=true)"
+    except OSError as exc:
+        return f"error: cannot move to trash: {exc}"
+    return None
diff --git a/tests/test_tools/test_fs_ops.py b/tests/test_tools/test_fs_ops.py
index 037b244..085096b 100644
--- a/tests/test_tools/test_fs_ops.py
+++ b/tests/test_tools/test_fs_ops.py
@@ -2,7 +2,9 @@ from __future__ import annotations
 
 from pathlib import Path
 
-from plyngent.tools.file import copy_path, delete_path, move_path, read_file, write_file
+import pytest
+
+from plyngent.tools.file import copy_path, delete_path, fs_ops, move_path, read_file, write_file
 from tests.test_tools.helpers import call_sync
 
 
@@ -75,6 +77,8 @@ def test_delete_nonempty_requires_recursive(workspace: object) -> None:
     out = call_sync(delete_path, "box")
     assert "not empty" in out
     assert (workspace / "box" / "a.txt").is_file()
+    # The workspace fixture lives under the system temp dir, so it is removed
+    # for good rather than trashed (see the trash tests below).
     out2 = call_sync(delete_path, "box", recursive=True)
     assert "recursive" in out2
     assert not (workspace / "box").exists()
@@ -97,3 +101,71 @@ def test_missing_source(workspace: object) -> None:
     assert "does not exist" in call_sync(copy_path, "nope", "x")
     assert "does not exist" in call_sync(move_path, "nope", "x")
     assert "does not exist" in call_sync(delete_path, "nope")
+
+
+def _elsewhere_than_temp(monkeypatch: pytest.MonkeyPatch) -> None:
+    """Pretend the workspace is not scratch space, so deletes use the trash."""
+    monkeypatch.setattr(fs_ops, "under_system_temp", lambda _path: False)
+
+
+def test_a_temp_path_is_deleted_for_good(workspace: object) -> None:
+    assert isinstance(workspace, Path)
+    _ = call_sync(write_file, "t.txt", "x")
+    out = call_sync(delete_path, "t.txt")
+    assert "trash" not in out
+    assert not (workspace / "t.txt").exists()
+
+
+def test_delete_goes_to_the_trash(workspace: object, monkeypatch: pytest.MonkeyPatch) -> None:
+    assert isinstance(workspace, Path)
+    _elsewhere_than_temp(monkeypatch)
+    trashed: list[Path] = []
+    monkeypatch.setattr(fs_ops, "move_to_trash", trashed.append)
+    _ = call_sync(write_file, "t.txt", "x")
+
+    out = call_sync(delete_path, "t.txt")
+
+    assert out == "deleted file t.txt (moved to system trash)"
+    assert [path.name for path in trashed] == ["t.txt"]
+
+
+def test_recursive_delete_goes_to_the_trash(workspace: object, monkeypatch: pytest.MonkeyPatch) -> None:
+    assert isinstance(workspace, Path)
+    _elsewhere_than_temp(monkeypatch)
+    trashed: list[Path] = []
+    monkeypatch.setattr(fs_ops, "move_to_trash", trashed.append)
+    _ = call_sync(write_file, "box/a.txt", "a")
+
+    out = call_sync(delete_path, "box", recursive=True)
+
+    assert out == "deleted directory box (moved to system trash)"
+    assert [path.name for path in trashed] == ["box"]
+
+
+def test_a_refused_trash_keeps_the_path(workspace: object, monkeypatch: pytest.MonkeyPatch) -> None:
+    assert isinstance(workspace, Path)
+    _elsewhere_than_temp(monkeypatch)
+    refused = "error: cannot move to trash: nope (use permanent=true)"
+    monkeypatch.setattr(fs_ops, "move_to_trash", lambda _target: refused)
+    _ = call_sync(write_file, "t.txt", "x")
+
+    out = call_sync(delete_path, "t.txt")
+
+    assert out == refused
+    assert (workspace / "t.txt").is_file()
+
+
+def test_permanent_delete_skips_the_trash(workspace: object, monkeypatch: pytest.MonkeyPatch) -> None:
+    assert isinstance(workspace, Path)
+
+    def _never(_target: Path) -> str | None:
+        msg = "a permanent delete must not touch the trash"
+        raise AssertionError(msg)
+
+    monkeypatch.setattr(fs_ops, "move_to_trash", _never)
+    _ = call_sync(write_file, "t.txt", "x")
+
+    out = call_sync(delete_path, "t.txt", permanent=True)
+
+    assert out == "deleted file t.txt"
+    assert not (workspace / "t.txt").exists()
diff --git a/tests/test_tools/test_trash.py b/tests/test_tools/test_trash.py
new file mode 100644
index 0000000..ea9694b
--- /dev/null
+++ b/tests/test_tools/test_trash.py
@@ -0,0 +1,130 @@
+from __future__ import annotations
+
+import os
+import sys
+from pathlib import Path
+
+import pytest
+import send2trash
+
+from plyngent.tools import trash
+from plyngent.tools.trash import is_available, move_to_trash, under_system_temp
+
+# The freedesktop implementation is the only one whose trash location can be
+# redirected for a test; macOS and Windows move into their own system trash.
+freedesktop_only = pytest.mark.skipif(sys.platform != "linux", reason="freedesktop trash only")
+
+
+@pytest.fixture
+def home_trash(tmp_path: Path, monkeypatch: pytest.MonkeyPatch) -> Path:
+    """Point the freedesktop implementation at a trash under *tmp_path*.
+
+    ``plat_other`` reads its trash locations from module globals computed at
+    import time and picks "home" vs "external volume" by device number, so both
+    are pinned here — otherwise a ``/tmp`` on a filesystem of its own would
+    create a real trash directory on that volume.
+    """
+    plat_other = pytest.importorskip("send2trash.plat_other")
+    root = tmp_path / "Trash"
+    monkeypatch.setattr(plat_other, "XDG_DATA_HOME", os.fsencode(str(tmp_path)))
+    monkeypatch.setattr(plat_other, "HOMETRASH_B", os.fsencode(str(root)))
+    monkeypatch.setattr(plat_other, "HOMETRASH", str(root))
+    monkeypatch.setattr(plat_other, "get_dev", lambda _path: 1)
+    # A GIO-backed install would otherwise bypass every patch above.
+    monkeypatch.setattr(send2trash, "send2trash", plat_other.send2trash)
+    return root
+
+
+def test_the_library_is_installed() -> None:
+    assert is_available()
+
+
+@freedesktop_only
+def test_move_to_trash_lands_in_the_trash(home_trash: Path, tmp_path: Path) -> None:
+    target = tmp_path / "gone.txt"
+    _ = target.write_text("x")
+
+    assert move_to_trash(target) is None
+
+    assert not target.exists()
+    assert (home_trash / "files" / "gone.txt").read_text() == "x"
+    entry = (home_trash / "info" / "gone.txt.trashinfo").read_text()
+    assert entry.startswith("[Trash Info]")
+    assert "Path=" in entry
+    assert "DeletionDate=" in entry
+
+
+@freedesktop_only
+def test_move_to_trash_moves_a_directory_in_one_piece(home_trash: Path, tmp_path: Path) -> None:
+    target = tmp_path / "box"
+    target.mkdir()
+    _ = (target / "inner.txt").write_text("x")
+
+    assert move_to_trash(target) is None
+
+    assert not target.exists()
+    assert (home_trash / "files" / "box" / "inner.txt").read_text() == "x"
+
+
+@freedesktop_only
+def test_trashing_twice_keeps_both_copies(home_trash: Path, tmp_path: Path) -> None:
+    first = tmp_path / "dup.txt"
+    second = tmp_path / "sub" / "dup.txt"
+    second.parent.mkdir()
+    _ = first.write_text("one")
+    _ = second.write_text("two")
+
+    assert move_to_trash(first) is None
+    assert move_to_trash(second) is None
+
+    names = sorted(path.name for path in (home_trash / "files").iterdir())
+    assert names == ["dup 1.txt", "dup.txt"]
+
+
+def test_a_refused_volume_names_the_escape_hatch(tmp_path: Path, monkeypatch: pytest.MonkeyPatch) -> None:
+    target = tmp_path / "gone.txt"
+    _ = target.write_text("x")
+
+    def _refuse(_paths: object) -> None:
+        raise send2trash.TrashPermissionError(str(target))
+
+    monkeypatch.setattr(send2trash, "send2trash", _refuse)
+
+    error = move_to_trash(target)
+
+    assert error is not None
+    assert error.startswith("error: cannot move to trash:")
+    assert "permanent=true" in error
+    assert target.is_file()
+
+
+def test_an_oserror_is_reported(tmp_path: Path, monkeypatch: pytest.MonkeyPatch) -> None:
+    target = tmp_path / "gone.txt"
+    _ = target.write_text("x")
+
+    def _fail(_paths: object) -> None:
+        raise OSError("disk on fire")
+
+    monkeypatch.setattr(send2trash, "send2trash", _fail)
+
+    assert move_to_trash(target) == "error: cannot move to trash: disk on fire"
+    assert target.is_file()
+
+
+def test_a_broken_install_leaves_the_file_alone(tmp_path: Path, monkeypatch: pytest.MonkeyPatch) -> None:
+    target = tmp_path / "gone.txt"
+    _ = target.write_text("x")
+    monkeypatch.setattr(trash, "is_available", lambda: False)
+
+    error = move_to_trash(target)
+
+    assert error is not None
+    assert "send2trash is not installed" in error
+    assert "permanent=true" in error
+    assert target.is_file()
+
+
+def test_under_system_temp(tmp_path: Path) -> None:
+    assert under_system_temp(tmp_path)
+    assert under_system_temp(tmp_path / "nested" / "file.txt")
+    assert not under_system_temp(Path("/plyngent-not-temp/deep/file.txt"))
diff --git a/typings/send2trash/__init__.pyi b/typings/send2trash/__init__.pyi
new file mode 100644
index 0000000..1232cb0
--- /dev/null
+++ b/typings/send2trash/__init__.pyi
@@ -0,0 +1,9 @@
+# Minimal stubs for ``send2trash`` (a required dependency).
+# Only the surface ``plyngent.tools.trash`` uses is declared; the real package is
+# pure Python over ctypes (freedesktop trash spec / Finder trash / Recycle Bin).
+
+from collections.abc import Iterable
+
+class TrashPermissionError(PermissionError): ...
+
+def send2trash(paths: str | Iterable[str]) -> None: ...