Win11 Delete key stops working for file deletion after renaming a file

This is expected clipboard-history behavior, not a synchronization failure. Windows clears unpinned clipboard-history entries when the computer restarts. Cross-device synchronization sends supported copied content between signed-in devices; it does not make the clipboard permanent or restore every previous-session item.

Open Win+V and pin any text or image you need after a restart. Test with one small text item: copy it, open Win+V, pin it, restart, and check again. Unpinned items should disappear, while the pinned item should remain. Clipboard history also has size and item-count limits, so it should not be used as a document archive.

If pinned items disappear, open Settings, System, Clipboard, turn Clipboard history off, restart, and enable it again. Install current Windows updates and retest with synchronization disabled first. If the pinned-item test still fails, report the Windows build and whether the device is managed, because organizational clipboard policies can disable or restrict history and synchronization.