diff --git a/windows-agent/agent/service.py b/windows-agent/agent/service.py
index fdde81b..22d26b2 100644
--- a/windows-agent/agent/service.py
+++ b/windows-agent/agent/service.py
@@ -23,6 +23,68 @@ logging.basicConfig(
 )
 logger = logging.getLogger("OnEverAgent")
 
+def send_to_recycle_bin(path_str: str) -> bool:
+    """
+    Sends a file or folder to the Windows Recycle Bin using native shell32 API.
+    """
+    try:
+        import ctypes
+        from ctypes import wintypes
+        
+        class SHFILEOPSTRUCTW(ctypes.Structure):
+            _fields_ = [
+                ("hwnd", wintypes.HWND),
+                ("wFunc", wintypes.UINT),
+                ("pFrom", ctypes.c_wchar_p),
+                ("pTo", ctypes.c_wchar_p),
+                ("fFlags", ctypes.c_ushort),
+                ("fAnyOperationsAborted", wintypes.BOOL),
+                ("hNameMappings", wintypes.LPVOID),
+                ("lpszProgressTitle", ctypes.c_wchar_p),
+            ]
+            
+        path_null = os.path.abspath(path_str) + "\0\0"
+        fileop = SHFILEOPSTRUCTW()
+        fileop.hwnd = None
+        fileop.wFunc = 3  # FO_DELETE
+        fileop.pFrom = path_null
+        fileop.pTo = None
+        # FOF_ALLOWUNDO (0x0040) sends to Recycle Bin. FOF_NOCONFIRMATION (0x0010) + FOF_NOERRORUI (0x0400) + FOF_SILENT (0x0004)
+        fileop.fFlags = 0x0040 | 0x0010 | 0x0400 | 0x0004
+        
+        res = ctypes.windll.shell32.SHFileOperationW(ctypes.byref(fileop))
+        return res == 0
+    except Exception as e:
+        logger.error(f"Failed to recycle bin file {path_str} via ctypes: {e}")
+        return False
+
+def resolve_path_tags(path: str) -> str:
+    """
+    Resolves Karen-style datetime tags inside file/folder paths.
+    """
+    now = datetime.now()
+    replacements = {
+        "<yyyy>": now.strftime("%Y"),
+        "<yy>": now.strftime("%y"),
+        "<year>": now.strftime("%Y"),
+        "<y>": now.strftime("%Y"),
+        "<month>": now.strftime("%b"),
+        "<mm>": now.strftime("%m"),
+        "<m>": str(now.month),
+        "<dd>": now.strftime("%d"),
+        "<d>": str(now.day),
+        "<dow>": str(now.weekday() + 1),
+        "<w>": str(now.weekday() + 1),
+        "<hour>": now.strftime("%H"),
+        "<hh>": now.strftime("%H"),
+        "<minute>": now.strftime("%M"),
+        "<min>": now.strftime("%M"),
+    }
+    resolved = path
+    for tag, val in replacements.items():
+        resolved = re.sub(re.escape(tag), val, resolved, flags=re.IGNORECASE)
+    return resolved
+
 def is_job_due(schedule_str: str, last_run_str: Optional[str]) -> bool:
     if not schedule_str:
         return True
@@ -368,7 +430,7 @@ class AgentDaemon:
 
             # Track files successfully backed up in this run
             active_relative_paths = []
-            dest_dir = getattr(job, "local_destination_path", None)
+            dest_dir = resolve_path_tags(getattr(job, "local_destination_path", None)) if getattr(job, "local_destination_path", None) else None
 
             for filepath in files:
                 rel_p = None
@@ -490,8 +552,11 @@ class AgentDaemon:
                             try:
                                 rel_to_dest = str(full_path.relative_to(dest_root)).replace("\\", "/")
                                 if rel_to_dest not in active_relative_paths:
-                                    logger.info(f"Removing local orphan file: {full_path}")
-                                    full_path.unlink()
+                                    logger.info(f"Recycling local orphan file: {full_path}")
+                                    recycled = send_to_recycle_bin(str(full_path))
+                                    if not recycled:
+                                        logger.info(f"Recycle bin failed. Permanently deleting local orphan file: {full_path}")
+                                        full_path.unlink()
                             except Exception as ex:
                                 logger.error(f"Error removing local orphan file {full_path}: {ex}")
                     for root, dirs, files_in_dir in os.walk(dest_root, topdown=False):
@@ -499,8 +564,11 @@ class AgentDaemon:
                             dir_path = Path(root) / dir_name
                             try:
                                 if not os.listdir(dir_path):
-                                    logger.info(f"Removing empty local directory: {dir_path}")
-                                    dir_path.rmdir()
+                                    logger.info(f"Recycling empty local directory: {dir_path}")
+                                    recycled = send_to_recycle_bin(str(dir_path))
+                                    if not recycled:
+                                        logger.info(f"Recycle bin failed. Permanently removing empty local directory: {dir_path}")
+                                        dir_path.rmdir()
                             except Exception:
                                 pass
                 except Exception as e:
diff --git a/windows-agent/agent_app_pyqt.py b/windows-agent/agent_app_pyqt.py
index 18ac1b5..b83fb59 100644
--- a/windows-agent/agent_app_pyqt.py
+++ b/windows-agent/agent_app_pyqt.py
@@ -271,11 +271,16 @@ class AddFolderDialog(QDialog):
 
         dest_layout = QHBoxLayout()
         self.txt_dest = QLineEdit()
-        self.txt_dest.setPlaceholderText("Ej: D:\\LocalBackup (Opcional)")
+        self.txt_dest.setPlaceholderText("Ej: D:\\LocalBackup\\<yyyy>-<mm>-<dd>")
         btn_browse_dest = QPushButton("Explorar...")
         btn_browse_dest.clicked.connect(self._browse_dest_folder)
+        
+        btn_tags = QPushButton("Tags...")
+        btn_tags.clicked.connect(self._show_tags_menu)
+        
         dest_layout.addWidget(self.txt_dest)
         dest_layout.addWidget(btn_browse_dest)
+        dest_layout.addWidget(btn_tags)
         form.addRow("Copia Local Adicional:", dest_layout)
 
         layout.addLayout(form)
@@ -304,6 +309,33 @@ class AddFolderDialog(QDialog):
         if folder:
             self.txt_dest.setText(folder)
 
+    def _show_tags_menu(self):
+        from PyQt6.QtWidgets import QMenu
+        from PyQt6.QtGui import QAction
+        
+        menu = QMenu(self)
+        tags = [
+            ("<yyyy>", "Año actual (4 dígitos)"),
+            ("<yy>", "Año actual (2 dígitos)"),
+            ("<month>", "Nombre del mes (ej: Jul)"),
+            ("<mm>", "Mes actual (01-12)"),
+            ("<m>", "Mes actual (1-12)"),
+            ("<dd>", "Día actual (01-31)"),
+            ("<d>", "Día actual (1-31)"),
+            ("<dow>", "Día de la semana (1=Lunes...7=Domingo)"),
+            ("<hour>", "Hora actual (00-23)"),
+            ("<minute>", "Minuto actual (00-59)")
+        ]
+        
+        for tag, desc in tags:
+            action = QAction(f"{tag} - {desc}", self)
+            action.triggered.connect(lambda checked=False, t=tag: self.txt_dest.insert(t))
+            menu.addAction(action)
+            
+        btn = self.sender()
+        if btn:
+            menu.exec(btn.mapToGlobal(btn.rect().bottomLeft()))
+
     def _validate_and_accept(self):
         if not self.txt_path.text() or not os.path.exists(self.txt_path.text()):
             QMessageBox.warning(self, "Ruta Inválida", "Por favor selecciona una carpeta existente en Windows.")