diff --git a/HISTORY.md b/HISTORY.md
index 43d24069..21635801 100644
--- a/HISTORY.md
+++ b/HISTORY.md
@@ -18,6 +18,24 @@
 # along with this program.  If not, see <https://www.gnu.org/licenses/>.
 -->
 
+## 0.2.284 - 2025-09-20
+
+- Uninstall Windows resize hooks during interpreter shutdown and register a
+  global cleanup handler so callbacks are never invoked after the GIL is
+  released, avoiding Tk crashes when detached windows close.
+- Keep window resize controllers removing native hooks even while Python is
+  finalizing so floating diagram windows stop receiving Win32 messages during
+  teardown.
+
+## 0.2.283 - 2025-09-19
+
+- Ensure detached tabs register with floating window resizers so diagrams resize
+  with their new host windows instead of the original notebooks, avoiding
+  crashes during window configuration.
+- Add a regression test covering the detachment flow to verify resized diagrams
+  are tracked by the floating window resizer and remain linked to their new
+  window instances.
+
 ## 0.2.282 - 2025-09-18
 
 - Harden ``cancel_after_events`` so it cancels pending Tk ``after`` jobs before
@@ -961,3 +979,4 @@
 - 0.1.2 - Clarified systems safety focus in description and About dialog.
 - 0.1.1 - Updated description and About dialog.
 - 0.1.0 - Added Help menu and version tracking.
+- 0.2.26 - Guard detached window resize hooks during interpreter shutdown to avoid crashes.
diff --git a/gui/utils/closable_notebook.py b/gui/utils/closable_notebook.py
index cbfa4de8..0438a656 100644
--- a/gui/utils/closable_notebook.py
+++ b/gui/utils/closable_notebook.py
@@ -941,8 +941,15 @@ def _on_destroy(_e, w=dw.win) -> None:
         except tk.TclError:
             logger.exception("Failed to detach tab %s", tab_id)
             return
-        dw._ensure_toolbox(child)
-        dw._activate_hooks(child)
+        try:
+            title = self.tab(child, "text")
+        except Exception:
+            title = ""
+        try:
+            dw.add_moved_widget(child, title)
+        except Exception:
+            dw._ensure_toolbox(child)
+            dw._activate_hooks(child)
 
     def rewrite_option_references(self, mapping: dict[tk.Widget, tk.Widget]) -> None:
         """Rewrite widget configuration options to point at cloned widgets."""
diff --git a/gui/utils/win32_hooks.py b/gui/utils/win32_hooks.py
index 84f905d1..c1302887 100644
--- a/gui/utils/win32_hooks.py
+++ b/gui/utils/win32_hooks.py
@@ -19,9 +19,11 @@
 
 from __future__ import annotations
 
+import atexit
 import logging
 import sys
 import typing as t
+import weakref
 
 LOGGER = logging.getLogger(__name__)
 
@@ -40,6 +42,8 @@ def _python_is_finalizing() -> bool:
     import ctypes
     from ctypes import wintypes
 
+    _HOOKS: "weakref.WeakSet[_Win32WindowProcHook]" = weakref.WeakSet()
+
     LRESULT = wintypes.LPARAM
     WNDPROC = ctypes.WINFUNCTYPE(
         LRESULT, wintypes.HWND, wintypes.UINT, wintypes.WPARAM, wintypes.LPARAM
@@ -128,6 +132,7 @@ def __init__(self, hwnd: int, callback: t.Callable[[int, int], None]) -> None:
             self._original: int | None = None
             self._wnd_proc = WNDPROC(self._procedure)
             self._install()
+            _HOOKS.add(self)
 
         def _install(self) -> None:
             proc_pointer = ctypes.cast(self._wnd_proc, ctypes.c_void_p).value
@@ -143,6 +148,10 @@ def uninstall(self) -> None:
                 _set_window_proc(self.hwnd, self._original)
             finally:
                 self._original = None
+                try:
+                    _HOOKS.discard(self)
+                except Exception:
+                    pass
 
         def _procedure(self, hwnd, msg, wparam, lparam):  # noqa: ANN001
             if _python_is_finalizing():
@@ -190,10 +199,29 @@ def _extract_windowpos_dimensions(lparam: int) -> tuple[int, int] | None:
             return int(windowpos.cx), int(windowpos.cy)
 
         def __del__(self) -> None:
+            if _python_is_finalizing():
+                try:
+                    _HOOKS.discard(self)
+                except Exception:
+                    pass
+                return
             try:
                 self.uninstall()
             except Exception:
                 LOGGER.debug("Ignoring error while uninstalling Win32 hook", exc_info=True)
+                try:
+                    _HOOKS.discard(self)
+                except Exception:
+                    pass
+
+    def _uninstall_registered_hooks() -> None:
+        for hook in list(_HOOKS):
+            try:
+                hook.uninstall()
+            except Exception:
+                LOGGER.debug("Ignoring error during registered hook uninstall", exc_info=True)
+
+    atexit.register(_uninstall_registered_hooks)
 else:  # pragma: no cover - exercised only on non-Windows platforms
 
     class _Win32WindowProcHook:  # type: ignore[no-redef]
diff --git a/gui/utils/window_resizer.py b/gui/utils/window_resizer.py
index e7546740..91e44345 100644
--- a/gui/utils/window_resizer.py
+++ b/gui/utils/window_resizer.py
@@ -19,12 +19,22 @@
 
 from __future__ import annotations
 
+import sys
 import tkinter as tk
 import typing as t
 
 from gui.utils.win32_hooks import create_window_size_hook
 
 
+def _python_is_finalizing() -> bool:
+    """Return ``True`` when the Python interpreter is shutting down."""
+
+    finalizing = getattr(sys, "is_finalizing", None)
+    if finalizing is None:
+        return False
+    return bool(finalizing())
+
+
 class WindowResizeController:
     """Propagate ``<Configure>`` events from a toplevel to tracked widgets."""
 
@@ -116,22 +126,7 @@ def _callback(event: tk.Event) -> None:
     def shutdown(self) -> None:
         """Release bindings and native hooks held by the controller."""
 
-        unbind = getattr(self.win, "unbind", None)
-        if callable(unbind):
-            if self._binding_id is not None:
-                try:
-                    unbind("<Configure>", self._binding_id)
-                except Exception:
-                    pass
-                self._binding_id = None
-            if self._destroy_binding_id is not None:
-                try:
-                    unbind("<Destroy>", self._destroy_binding_id)
-                except Exception:
-                    pass
-                self._destroy_binding_id = None
-
-        self._callback = None
+        finalizing = _python_is_finalizing()
 
         hook = self._win32_hook
         if hook is not None:
@@ -141,6 +136,23 @@ def shutdown(self) -> None:
                 pass
             self._win32_hook = None
 
+        if not finalizing:
+            unbind = getattr(self.win, "unbind", None)
+            if callable(unbind):
+                if self._binding_id is not None:
+                    try:
+                        unbind("<Configure>", self._binding_id)
+                    except Exception:
+                        pass
+                    self._binding_id = None
+                if self._destroy_binding_id is not None:
+                    try:
+                        unbind("<Destroy>", self._destroy_binding_id)
+                    except Exception:
+                        pass
+                    self._destroy_binding_id = None
+
+        self._callback = None
         self._targets.clear()
         self._primary = None
         self._last_size = None
@@ -319,6 +331,8 @@ def _notify(widget: tk.Widget, width: int, height: int) -> None:
                 pass
 
     def __del__(self) -> None:  # pragma: no cover - defensive cleanup
+        if _python_is_finalizing():
+            return
         try:
             self.shutdown()
         except Exception:
diff --git a/tests/detachment/window/test_closable_notebook_detach_resize.py b/tests/detachment/window/test_closable_notebook_detach_resize.py
new file mode 100644
index 00000000..d1343576
--- /dev/null
+++ b/tests/detachment/window/test_closable_notebook_detach_resize.py
@@ -0,0 +1,95 @@
+# Author: Miguel Marina <karel.capek.robotics@gmail.com>
+# SPDX-License-Identifier: GPL-3.0-or-later
+#
+# Copyright (C) 2025 Capek System Safety & Robotic Solutions
+#
+# This program is free software: you can redistribute it and/or modify
+# it under the terms of the GNU General Public License as published by
+# the Free Software Foundation, either version 3 of the License, or
+# (at your option) any later version.
+#
+# This program is distributed in the hope that it will be useful,
+# but WITHOUT ANY WARRANTY; without even the implied warranty of
+# MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+# GNU General Public License for more details.
+#
+# You should have received a copy of the GNU General Public License
+# along with this program.  If not, see <https://www.gnu.org/licenses/>.
+
+"""Regression tests for detaching tabs into floating windows."""
+
+from __future__ import annotations
+
+import tkinter as tk
+from tkinter import ttk
+
+import pytest
+
+from gui.utils.closable_notebook import ClosableNotebook
+
+
+@pytest.mark.detachment
+@pytest.mark.window_resizer
+class TestClosableNotebookDetachment:
+    """Ensure detached tabs register with the floating window resizer."""
+
+    def test_detach_tab_registers_resizer(
+        self, monkeypatch: pytest.MonkeyPatch
+    ) -> None:
+        try:
+            root = tk.Tk()
+        except tk.TclError:
+            pytest.skip("Tk not available")
+
+        notebook = ClosableNotebook(root)
+        frame = tk.Frame(notebook)
+        notebook.add(frame, text="Diagram")
+
+        class StubWindow:
+            def __init__(self, *_args, **_kwargs) -> None:
+                self.win = tk.Toplevel(root)
+                self.nb = ttk.Notebook(self.win)
+                self.added: list[tuple[tk.Widget, str]] = []
+
+            def add_moved_widget(self, widget: tk.Widget, text: str) -> None:
+                self.added.append((widget, text))
+
+            def _ensure_toolbox(self, widget: tk.Widget) -> None:  # noqa: ANN001 - stub API
+                self.added.append((widget, "toolbox"))
+
+            def _activate_hooks(self, widget: tk.Widget) -> None:  # noqa: ANN001 - stub API
+                self.added.append((widget, "hooks"))
+
+        stub_windows: list[StubWindow] = []
+        monkeypatch.setattr(
+            "gui.utils.closable_notebook.DetachedWindow",
+            lambda *args, **kwargs: stub_windows.append(StubWindow(*args, **kwargs))
+            or stub_windows[-1],
+        )
+
+        class StubManager:
+            def __init__(self) -> None:
+                self.calls: list[tuple[tk.Widget, str, tk.Widget]] = []
+
+            def detach_tab(
+                self, source: tk.Widget, tab_id: str, target: tk.Widget
+            ) -> tk.Widget:
+                self.calls.append((source, tab_id, target))
+                source.forget(tab_id)
+                target.add(frame, text="Diagram")
+                return frame
+
+        manager = StubManager()
+        monkeypatch.setattr(
+            "gui.utils.closable_notebook.WidgetTransferManager", lambda: manager
+        )
+
+        notebook._detach_tab(str(frame), x=10, y=10)
+
+        assert stub_windows, "DetachedWindow should have been instantiated"
+        window = stub_windows[0]
+        assert window.added[0] == (frame, "Diagram")
+        assert manager.calls and manager.calls[0][0] is notebook
+
+        window.win.destroy()
+        root.destroy()
diff --git a/tests/detachment/window/test_window_resizer_finalization.py b/tests/detachment/window/test_window_resizer_finalization.py
new file mode 100644
index 00000000..fc6a12ee
--- /dev/null
+++ b/tests/detachment/window/test_window_resizer_finalization.py
@@ -0,0 +1,54 @@
+# Author: Miguel Marina <karel.capek.robotics@gmail.com>
+# SPDX-License-Identifier: GPL-3.0-or-later
+#
+# Copyright (C) 2025 Capek System Safety & Robotic Solutions
+#
+# This program is free software: you can redistribute it and/or modify
+# it under the terms of the GNU General Public License as published by
+# the Free Software Foundation, either version 3 of the License, or
+# (at your option) any later version.
+#
+# This program is distributed in the hope that it will be useful,
+# but WITHOUT ANY WARRANTY; without even the implied warranty of
+# MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+# GNU General Public License for more details.
+#
+# You should have received a copy of the GNU General Public License
+# along with this program.  If not, see <https://www.gnu.org/licenses/>.
+
+"""Finalization safety for the window resize controller."""
+
+from __future__ import annotations
+
+import gui.utils.window_resizer as window_resizer
+
+
+class _StubWindow:
+    def __init__(self) -> None:
+        self.unbind_calls: list[tuple[tuple[str, str], dict[str, str]]] = []
+
+    def wm_resizable(self, *_args, **_kwargs) -> None:  # pragma: no cover - noop
+        return None
+
+    def bind(self, *args, **_kwargs) -> str:  # pragma: no cover - basic stub
+        return f"bind-{args[0]}"
+
+    def unbind(self, *args, **kwargs) -> None:  # pragma: no cover - tracking only
+        self.unbind_calls.append((args, kwargs))
+
+    def winfo_id(self) -> None:  # pragma: no cover - disable Win32 hook install
+        return None
+
+
+def test_shutdown_skips_finalizing(monkeypatch) -> None:
+    """Ensure shutdown avoids Tk/Win32 work during interpreter finalization."""
+
+    win = _StubWindow()
+    monkeypatch.setattr(window_resizer, "_python_is_finalizing", lambda: False)
+    controller = window_resizer.WindowResizeController(win)
+    monkeypatch.setattr(window_resizer, "_python_is_finalizing", lambda: True)
+
+    controller.shutdown()
+
+    assert win.unbind_calls == []
+