diff --git a/requirements.txt b/requirements.txt
index 9eb290390..ff6e6d4ab 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -12,6 +12,7 @@ PySide6_Addons==6.8.0.1
 PySide6_Essentials==6.8.0.1
 PySide6==6.8.0.1
 rawpy==0.22.0
+Send2Trash==1.8.3
 SQLAlchemy==2.0.34
 structlog==24.4.0
 typing_extensions>=3.10.0.0,<=4.11.0
diff --git a/tagstudio/resources/qt/videos/placeholder.mp4 b/tagstudio/resources/qt/videos/placeholder.mp4
new file mode 100644
index 000000000..1e22e4c72
Binary files /dev/null and b/tagstudio/resources/qt/videos/placeholder.mp4 differ
diff --git a/tagstudio/resources/translations/en.json b/tagstudio/resources/translations/en.json
index 4776c1a01..7608d3cae 100644
--- a/tagstudio/resources/translations/en.json
+++ b/tagstudio/resources/translations/en.json
@@ -157,6 +157,9 @@
     "macros.running.dialog.new_entries": "Running Configured Macros on {count}/{total} New File Entries...",
     "macros.running.dialog.title": "Running Macros on New Entries",
     "media_player.autoplay": "Autoplay",
+    "menu.delete_selected_files_ambiguous": "Move File(s) to {trash_term}",
+    "menu.delete_selected_files_plural": "Move Files to {trash_term}",
+    "menu.delete_selected_files_singular": "Move File to {trash_term}",
     "menu.edit.ignore_list": "Ignore Files and Folders",
     "menu.edit.manage_file_extensions": "Manage File Extensions",
     "menu.edit.manage_tags": "Manage Tags",
@@ -195,6 +198,11 @@
     "sorting.direction.ascending": "Ascending",
     "sorting.direction.descending": "Descending",
     "splash.opening_library": "Opening Library \"{library_path}\"...",
+    "status.deleted_file_plural": "Deleted {count} files!",
+    "status.deleted_file_singular": "Deleted 1 file!",
+    "status.deleted_none": "No files deleted.",
+    "status.deleted_partial_warning": "Only deleted {count} file(s)! Check if any of the files are currently missing or in use.",
+    "status.deleting_file": "Deleting file [{i}/{count}]: \"{path}\"...",
     "status.library_backup_in_progress": "Saving Library Backup...",
     "status.library_backup_success": "Library Backup Saved at: \"{path}\" ({time_span})",
     "status.library_closed": "Library Closed ({time_span})",
@@ -230,6 +238,18 @@
     "tag.shorthand": "Shorthand",
     "tag.tag_name_required": "Tag Name (Required)",
     "tag.view_limit": "View Limit:",
+    "trash.context.ambiguous": "Move file(s) to {trash_term}",
+    "trash.context.plural": "Move files to {trash_term}",
+    "trash.context.singular": "Move file to {trash_term}",
+    "trash.dialog.disambiguation_warning.plural": "This will remove them from TagStudio <i>AND</i> your file system!",
+    "trash.dialog.disambiguation_warning.singular": "This will remove it from TagStudio <i>AND</i> your file system!",
+    "trash.dialog.move.confirmation.plural": "Are you sure you want to move these {count} files to the {trash_term}?",
+    "trash.dialog.move.confirmation.singular": "Are you sure you want to move this file to the {trash_term}?",
+    "trash.dialog.permanent_delete_warning": "<b>WARNING!</b> If this file can't be moved to the {trash_term}, <b>it will be <b>permanently deleted!</b>",
+    "trash.dialog.title.plural": "Delete Files",
+    "trash.dialog.title.singular": "Delete File",
+    "trash.name.generic": "Trash",
+    "trash.name.windows": "Recycle Bin",
     "view.size.0": "Mini",
     "view.size.1": "Small",
     "view.size.2": "Medium",
diff --git a/tagstudio/src/qt/helpers/file_deleter.py b/tagstudio/src/qt/helpers/file_deleter.py
new file mode 100644
index 000000000..a8e50e17c
--- /dev/null
+++ b/tagstudio/src/qt/helpers/file_deleter.py
@@ -0,0 +1,30 @@
+# Copyright (C) 2025 Travis Abendshien (CyanVoxel).
+# Licensed under the GPL-3.0 License.
+# Created for TagStudio: https://github.com/CyanVoxel/TagStudio
+
+import logging
+from pathlib import Path
+
+from send2trash import send2trash
+
+logging.basicConfig(format="%(message)s", level=logging.INFO)
+
+
+def delete_file(path: str | Path) -> bool:
+    """Send a file to the system trash.
+
+    Args:
+        path (str | Path): The path of the file to delete.
+    """
+    _path = Path(path)
+    try:
+        logging.info(f"[delete_file] Sending to Trash: {_path}")
+        send2trash(_path)
+        return True
+    except PermissionError as e:
+        logging.error(f"[delete_file][ERROR] PermissionError: {e}")
+    except FileNotFoundError:
+        logging.error(f"[delete_file][ERROR] File Not Found: {_path}")
+    except Exception as e:
+        logging.error(e)
+    return False
diff --git a/tagstudio/src/qt/platform_strings.py b/tagstudio/src/qt/platform_strings.py
index 23851dd48..70426b12c 100644
--- a/tagstudio/src/qt/platform_strings.py
+++ b/tagstudio/src/qt/platform_strings.py
@@ -1,4 +1,4 @@
-# Copyright (C) 2024 Travis Abendshien (CyanVoxel).
+# Copyright (C) 2025 Travis Abendshien (CyanVoxel).
 # Licensed under the GPL-3.0 License.
 # Created for TagStudio: https://github.com/CyanVoxel/TagStudio
 
@@ -9,10 +9,17 @@
 from src.qt.translations import Translations
 
 
-class PlatformStrings:
-    open_file_str: str = Translations["file.open_location.generic"]
-
+def open_file_str() -> str:
     if platform.system() == "Windows":
-        open_file_str = Translations["file.open_location.windows"]
+        return Translations["file.open_location.windows"]
     elif platform.system() == "Darwin":
-        open_file_str = Translations["file.open_location.mac"]
+        return Translations["file.open_location.mac"]
+    else:
+        return Translations["file.open_location.generic"]
+
+
+def trash_term() -> str:
+    if platform.system() == "Windows":
+        return Translations["trash.name.windows"]
+    else:
+        return Translations["trash.name.generic"]
diff --git a/tagstudio/src/qt/ts_qt.py b/tagstudio/src/qt/ts_qt.py
index 9c732b1cf..3e3c83904 100644
--- a/tagstudio/src/qt/ts_qt.py
+++ b/tagstudio/src/qt/ts_qt.py
@@ -7,6 +7,7 @@
 
 """A Qt driver for TagStudio."""
 
+import contextlib
 import ctypes
 import dataclasses
 import math
@@ -67,6 +68,7 @@
 from src.core.library.alchemy.fields import _FieldID
 from src.core.library.alchemy.library import Entry, LibraryStatus
 from src.core.media_types import MediaCategories
+from src.core.palette import ColorType, UiColor, get_ui_color
 from src.core.query_lang.util import ParsingError
 from src.core.ts_core import TagStudioCore
 from src.core.utils.refresh_dir import RefreshDirTracker
@@ -74,6 +76,7 @@
 from src.qt.cache_manager import CacheManager
 from src.qt.flowlayout import FlowLayout
 from src.qt.helpers.custom_runnable import CustomRunnable
+from src.qt.helpers.file_deleter import delete_file
 from src.qt.helpers.function_iterator import FunctionIterator
 from src.qt.main_window import Ui_MainWindow
 from src.qt.modals.about import AboutModal
@@ -86,6 +89,7 @@
 from src.qt.modals.folders_to_tags import FoldersToTagsModal
 from src.qt.modals.tag_database import TagDatabasePanel
 from src.qt.modals.tag_search import TagSearchPanel
+from src.qt.platform_strings import trash_term
 from src.qt.resource_manager import ResourceManager
 from src.qt.splash import Splash
 from src.qt.translations import Translations
@@ -498,6 +502,17 @@ def start(self) -> None:
 
         edit_menu.addSeparator()
 
+        self.delete_file_action = QAction(menu_bar)
+        Translations.translate_qobject(
+            self.delete_file_action, "menu.delete_selected_files_ambiguous", trash_term=trash_term()
+        )
+        self.delete_file_action.triggered.connect(lambda f="": self.delete_files_callback(f))
+        self.delete_file_action.setShortcut(QtCore.Qt.Key.Key_Delete)
+        self.delete_file_action.setEnabled(False)
+        edit_menu.addAction(self.delete_file_action)
+
+        edit_menu.addSeparator()
+
         self.manage_file_ext_action = QAction(menu_bar)
         Translations.translate_qobject(
             self.manage_file_ext_action, "menu.edit.manage_file_extensions"
@@ -839,10 +854,13 @@ def close_library(self, is_shutdown: bool = False):
 
         self.main_window.setWindowTitle(self.base_title)
 
-        self.selected = []
-        self.frame_content = []
+        self.selected.clear()
+        self.frame_content.clear()
         [x.set_mode(None) for x in self.item_thumbs]
 
+        self.set_clipboard_menu_viability()
+        self.set_select_actions_visibility()
+
         self.preview_panel.update_widgets()
         self.main_window.toggle_landing_page(enabled=True)
         self.main_window.pagination.setHidden(True)
@@ -937,6 +955,141 @@ def add_tags_to_selected_callback(self, tag_ids: list[int]):
         for entry_id in self.selected:
             self.lib.add_tags_to_entry(entry_id, tag_ids)
 
+    def delete_files_callback(self, origin_path: str | Path, origin_id: int | None = None):
+        """Callback to send on or more files to the system trash.
+
+        If 0-1 items are currently selected, the origin_path is used to delete the file
+        from the originating context menu item.
+        If there are currently multiple items selected,
+        then the selection buffer is used to determine the files to be deleted.
+
+        Args:
+            origin_path(str): The file path associated with the widget making the call.
+                May or may not be the file targeted, depending on the selection rules.
+            origin_id(id): The entry ID associated with the widget making the call.
+        """
+        entry: Entry | None = None
+        pending: list[tuple[int, Path]] = []
+        deleted_count: int = 0
+
+        if len(self.selected) <= 1 and origin_path:
+            origin_id_ = origin_id
+            if not origin_id_:
+                with contextlib.suppress(IndexError):
+                    origin_id_ = self.selected[0]
+
+            pending.append((origin_id_, Path(origin_path)))
+        elif (len(self.selected) > 1) or (len(self.selected) <= 1):
+            for item in self.selected:
+                entry = self.lib.get_entry(item)
+                filepath: Path = entry.path
+                pending.append((item, filepath))
+
+        if pending:
+            return_code = self.delete_file_confirmation(len(pending), pending[0][1])
+            # If there was a confirmation and not a cancellation
+            if (
+                return_code == QMessageBox.ButtonRole.DestructiveRole.value
+                and return_code != QMessageBox.ButtonRole.ActionRole.value
+            ):
+                for i, tup in enumerate(pending):
+                    e_id, f = tup
+                    if (origin_path == f) or (not origin_path):
+                        self.preview_panel.thumb.stop_file_use()
+                    if delete_file(self.lib.library_dir / f):
+                        self.main_window.statusbar.showMessage(
+                            Translations.translate_formatted(
+                                "status.deleting_file", i=i, count=len(pending), path=f
+                            )
+                        )
+                        self.main_window.statusbar.repaint()
+                        self.lib.remove_entries([e_id])
+
+                        deleted_count += 1
+                self.selected.clear()
+
+        if deleted_count > 0:
+            self.filter_items()
+            self.preview_panel.update_widgets()
+
+        if len(self.selected) <= 1 and deleted_count == 0:
+            self.main_window.statusbar.showMessage(Translations["status.deleted_none"])
+        elif len(self.selected) <= 1 and deleted_count == 1:
+            self.main_window.statusbar.showMessage(
+                Translations.translate_formatted("status.deleted_file_plural", count=deleted_count)
+            )
+        elif len(self.selected) > 1 and deleted_count == 0:
+            self.main_window.statusbar.showMessage(Translations["status.deleted_none"])
+        elif len(self.selected) > 1 and deleted_count < len(self.selected):
+            self.main_window.statusbar.showMessage(
+                Translations.translate_formatted(
+                    "status.deleted_partial_warning", count=deleted_count
+                )
+            )
+        elif len(self.selected) > 1 and deleted_count == len(self.selected):
+            self.main_window.statusbar.showMessage(
+                Translations.translate_formatted("status.deleted_file_plural", count=deleted_count)
+            )
+        self.main_window.statusbar.repaint()
+
+    def delete_file_confirmation(self, count: int, filename: Path | None = None) -> int:
+        """A confirmation dialogue box for deleting files.
+
+        Args:
+            count(int): The number of files to be deleted.
+            filename(Path | None): The filename to show if only one file is to be deleted.
+        """
+        # NOTE: Windows + send2trash will PERMANENTLY delete files which cannot be moved to the
+        # Recycle Bin. This is done without any warning, so this message is currently the
+        # best way I've got to inform the user.
+        # https://github.com/arsenetar/send2trash/issues/28
+        # This warning is applied to all platforms until at least macOS and Linux can be verified
+        # to not exhibit this same behavior.
+        perm_warning_msg = Translations.translate_formatted(
+            "trash.dialog.permanent_delete_warning", trash_term=trash_term()
+        )
+        perm_warning: str = (
+            f"<h4 style='color: {get_ui_color(ColorType.PRIMARY, UiColor.RED)}'>"
+            f"{perm_warning_msg}</h4>"
+        )
+
+        msg = QMessageBox()
+        msg.setStyleSheet("font-weight:normal;")
+        msg.setTextFormat(Qt.TextFormat.RichText)
+        msg.setWindowTitle(
+            Translations["trash.title.singular"]
+            if count == 1
+            else Translations["trash.title.plural"]
+        )
+        msg.setIcon(QMessageBox.Icon.Warning)
+        if count <= 1:
+            msg_text = Translations.translate_formatted(
+                "trash.dialog.move.confirmation.singular", trash_term=trash_term()
+            )
+            msg.setText(
+                f"<h3>{msg_text}</h3>"
+                f"<h4>{Translations["trash.dialog.disambiguation_warning.singular"]}</h4>"
+                f"{filename if filename else ''}"
+                f"{perm_warning}<br>"
+            )
+        elif count > 1:
+            msg_text = Translations.translate_formatted(
+                "trash.dialog.move.confirmation.plural",
+                count=count,
+                trash_term=trash_term(),
+            )
+            msg.setText(
+                f"<h3>{msg_text}</h3>"
+                f"<h4>{Translations["trash.dialog.disambiguation_warning.plural"]}</h4>"
+                f"{perm_warning}<br>"
+            )
+
+        yes_button: QPushButton = msg.addButton("&Yes", QMessageBox.ButtonRole.YesRole)
+        msg.addButton("&No", QMessageBox.ButtonRole.NoRole)
+        msg.setDefaultButton(yes_button)
+
+        return msg.exec()
+
     def add_new_files_callback(self):
         """Run when user initiates adding new files to the Library."""
         tracker = RefreshDirTracker(self.lib)
@@ -1315,9 +1468,11 @@ def set_select_actions_visibility(self):
         if self.selected:
             self.add_tag_to_selected_action.setEnabled(True)
             self.clear_select_action.setEnabled(True)
+            self.delete_file_action.setEnabled(True)
         else:
             self.add_tag_to_selected_action.setEnabled(False)
             self.clear_select_action.setEnabled(False)
+            self.delete_file_action.setEnabled(False)
 
     def update_completions_list(self, text: str) -> None:
         matches = re.search(
@@ -1425,6 +1580,9 @@ def update_thumbs(self):
             if not entry:
                 continue
 
+            with catch_warnings(record=True):
+                item_thumb.delete_action.triggered.disconnect()
+
             item_thumb.set_mode(ItemType.ENTRY)
             item_thumb.set_item_id(entry.id)
             item_thumb.show()
@@ -1470,6 +1628,11 @@ def update_thumbs(self):
                     )
                 )
             )
+            item_thumb.delete_action.triggered.connect(
+                lambda checked=False, f=filenames[index], e_id=entry.id: self.delete_files_callback(
+                    f, e_id
+                )
+            )
 
             # Restore Selected Borders
             is_selected = item_thumb.item_id in self.selected
diff --git a/tagstudio/src/qt/widgets/item_thumb.py b/tagstudio/src/qt/widgets/item_thumb.py
index 008aaa72e..2ec049667 100644
--- a/tagstudio/src/qt/widgets/item_thumb.py
+++ b/tagstudio/src/qt/widgets/item_thumb.py
@@ -29,7 +29,7 @@
 from src.core.media_types import MediaCategories, MediaType
 from src.qt.flowlayout import FlowWidget
 from src.qt.helpers.file_opener import FileOpenerHelper
-from src.qt.platform_strings import PlatformStrings
+from src.qt.platform_strings import open_file_str, trash_term
 from src.qt.translations import Translations
 from src.qt.widgets.thumb_button import ThumbButton
 from src.qt.widgets.thumb_renderer import ThumbRenderer
@@ -219,10 +219,17 @@ def __init__(
         open_file_action = QAction(self)
         Translations.translate_qobject(open_file_action, "file.open_file")
         open_file_action.triggered.connect(self.opener.open_file)
-        open_explorer_action = QAction(PlatformStrings.open_file_str, self)
+        open_explorer_action = QAction(open_file_str(), self)
         open_explorer_action.triggered.connect(self.opener.open_explorer)
+
+        self.delete_action = QAction(self)
+        Translations.translate_qobject(
+            self.delete_action, "trash.context.ambiguous", trash_term=trash_term()
+        )
+
         self.thumb_button.addAction(open_file_action)
         self.thumb_button.addAction(open_explorer_action)
+        self.thumb_button.addAction(self.delete_action)
 
         # Static Badges ========================================================
 
diff --git a/tagstudio/src/qt/widgets/preview/preview_thumb.py b/tagstudio/src/qt/widgets/preview/preview_thumb.py
index 247c7a5b3..137b2dea7 100644
--- a/tagstudio/src/qt/widgets/preview/preview_thumb.py
+++ b/tagstudio/src/qt/widgets/preview/preview_thumb.py
@@ -6,6 +6,7 @@
 import time
 import typing
 from pathlib import Path
+from warnings import catch_warnings
 
 import cv2
 import rawpy
@@ -24,7 +25,8 @@
 from src.qt.helpers.file_tester import is_readable_video
 from src.qt.helpers.qbutton_wrapper import QPushButtonWrapper
 from src.qt.helpers.rounded_pixmap_style import RoundedPixmapStyle
-from src.qt.platform_strings import PlatformStrings
+from src.qt.platform_strings import open_file_str, trash_term
+from src.qt.resource_manager import ResourceManager
 from src.qt.translations import Translations
 from src.qt.widgets.media_player import MediaPlayer
 from src.qt.widgets.thumb_renderer import ThumbRenderer
@@ -54,7 +56,11 @@ def __init__(self, library: Library, driver: "QtDriver"):
 
         self.open_file_action = QAction(self)
         Translations.translate_qobject(self.open_file_action, "file.open_file")
-        self.open_explorer_action = QAction(PlatformStrings.open_file_str, self)
+        self.open_explorer_action = QAction(open_file_str(), self)
+        self.delete_action = QAction(self)
+        Translations.translate_qobject(
+            self.delete_action, "trash.context.ambiguous", trash_term=trash_term()
+        )
 
         self.preview_img = QPushButtonWrapper()
         self.preview_img.setMinimumSize(*self.img_button_size)
@@ -62,6 +68,7 @@ def __init__(self, library: Library, driver: "QtDriver"):
         self.preview_img.setContextMenuPolicy(Qt.ContextMenuPolicy.ActionsContextMenu)
         self.preview_img.addAction(self.open_file_action)
         self.preview_img.addAction(self.open_explorer_action)
+        self.preview_img.addAction(self.delete_action)
 
         self.preview_gif = QLabel()
         self.preview_gif.setMinimumSize(*self.img_button_size)
@@ -69,10 +76,12 @@ def __init__(self, library: Library, driver: "QtDriver"):
         self.preview_gif.setCursor(Qt.CursorShape.ArrowCursor)
         self.preview_gif.addAction(self.open_file_action)
         self.preview_gif.addAction(self.open_explorer_action)
+        self.preview_gif.addAction(self.delete_action)
         self.preview_gif.hide()
         self.gif_buffer: QBuffer = QBuffer()
 
         self.preview_vid = VideoPlayer(driver)
+        self.preview_vid.addAction(self.delete_action)
         self.preview_vid.hide()
         self.thumb_renderer = ThumbRenderer(self.lib)
         self.thumb_renderer.updated.connect(lambda ts, i, s: (self.preview_img.setIcon(i)))
@@ -355,7 +364,7 @@ def update_preview(self, filepath: Path, ext: str) -> dict:
                 update_on_ratio_change=True,
             )
 
-        if self.preview_img.is_connected:
+        with catch_warnings(record=True):
             self.preview_img.clicked.disconnect()
         self.preview_img.clicked.connect(lambda checked=False, path=filepath: open_file(path))
         self.preview_img.is_connected = True
@@ -367,12 +376,31 @@ def update_preview(self, filepath: Path, ext: str) -> dict:
         self.open_file_action.triggered.connect(self.opener.open_file)
         self.open_explorer_action.triggered.connect(self.opener.open_explorer)
 
+        with catch_warnings(record=True):
+            self.delete_action.triggered.disconnect()
+
+        self.delete_action.setText(
+            Translations.translate_formatted("trash.context.singular", trash_term=trash_term())
+        )
+        self.delete_action.triggered.connect(
+            lambda checked=False, f=filepath: self.driver.delete_files_callback(f)
+        )
+        self.delete_action.setEnabled(bool(filepath))
+
         return stats
 
     def hide_preview(self):
         """Completely hide the file preview."""
         self.switch_preview("")
 
+    def stop_file_use(self):
+        """Stops the use of the currently previewed file. Used to release file permissions."""
+        logger.info("[PreviewThumb] Stopping file use in video playback...")
+        # This swaps the video out for a placeholder so the previous video's file
+        # is no longer in use by this object.
+        self.preview_vid.play(str(ResourceManager.get_path("placeholder_mp4")), QSize(8, 8))
+        self.preview_vid.hide()
+
     def resizeEvent(self, event: QResizeEvent) -> None:  # noqa: N802
         self.update_image_size((self.size().width(), self.size().height()))
         return super().resizeEvent(event)
diff --git a/tagstudio/src/qt/widgets/video_player.py b/tagstudio/src/qt/widgets/video_player.py
index 7e5e6ba15..d02a06e49 100644
--- a/tagstudio/src/qt/widgets/video_player.py
+++ b/tagstudio/src/qt/widgets/video_player.py
@@ -30,7 +30,7 @@
 from PySide6.QtWidgets import QGraphicsScene, QGraphicsView
 from src.core.enums import SettingItems
 from src.qt.helpers.file_opener import FileOpenerHelper
-from src.qt.platform_strings import PlatformStrings
+from src.qt.platform_strings import open_file_str
 from src.qt.translations import Translations
 
 if typing.TYPE_CHECKING:
@@ -130,7 +130,7 @@ def __init__(self, driver: "QtDriver") -> None:
         Translations.translate_qobject(open_file_action, "file.open_file")
         open_file_action.triggered.connect(self.opener.open_file)
 
-        open_explorer_action = QAction(PlatformStrings.open_file_str, self)
+        open_explorer_action = QAction(open_file_str(), self)
 
         open_explorer_action.triggered.connect(self.opener.open_explorer)
         self.addAction(open_file_action)