diff --git a/i18n/en/cosmic_files.ftl b/i18n/en/cosmic_files.ftl
index a8dc296..9139d5d 100644
--- a/i18n/en/cosmic_files.ftl
+++ b/i18n/en/cosmic_files.ftl
@@ -181,6 +181,14 @@ copied = Copied {$items} {$items ->
         [one] item
         *[other] items
     } from "{$from}" to "{$to}"
+deleting = Deleting {$items} {$items ->
+        [one] item
+        *[other] items
+    } from {trash} ({$progress})...
+deleted = Deleted {$items} {$items ->
+        [one] item
+        *[other] items
+    } from {trash}
 emptying-trash = Emptying {trash} ({$progress})...
 emptied-trash = Emptied {trash}
 extracting = Extracting {$items} {$items ->
@@ -240,6 +248,7 @@ light = Light
 # Context menu
 add-to-sidebar = Add to sidebar
 compress = Compress
+delete-permanently = Delete permanently
 extract-here = Extract
 new-file = New file...
 new-folder = New folder...
diff --git a/src/app.rs b/src/app.rs
index f866686..c99aed4 100644
--- a/src/app.rs
+++ b/src/app.rs
@@ -100,6 +100,7 @@ pub enum Action {
     CosmicSettingsDisplays,
     CosmicSettingsWallpaper,
     DesktopViewOptions,
+    Delete,
     EditHistory,
     EditLocation,
     EmptyTrash,
@@ -114,7 +115,6 @@ pub enum Action {
     ItemRight,
     ItemUp,
     LocationUp,
-    MoveToTrash,
     NewFile,
     NewFolder,
     Open,
@@ -161,6 +161,7 @@ impl Action {
             Action::CosmicSettingsAppearance => Message::CosmicSettings("appearance"),
             Action::CosmicSettingsDisplays => Message::CosmicSettings("displays"),
             Action::CosmicSettingsWallpaper => Message::CosmicSettings("wallpaper"),
+            Action::Delete => Message::Delete(entity_opt),
             Action::DesktopViewOptions => Message::DesktopViewOptions,
             Action::EditHistory => Message::ToggleContextPage(ContextPage::EditHistory),
             Action::EditLocation => {
@@ -180,7 +181,6 @@ impl Action {
             Action::ItemRight => Message::TabMessage(entity_opt, tab::Message::ItemRight),
             Action::ItemUp => Message::TabMessage(entity_opt, tab::Message::ItemUp),
             Action::LocationUp => Message::TabMessage(entity_opt, tab::Message::LocationUp),
-            Action::MoveToTrash => Message::MoveToTrash(entity_opt),
             Action::NewFile => Message::NewItem(entity_opt, false),
             Action::NewFolder => Message::NewItem(entity_opt, true),
             Action::Open => Message::TabMessage(entity_opt, tab::Message::Open(None)),
@@ -281,6 +281,7 @@ pub enum Message {
     CosmicSettings(&'static str),
     CursorMoved(Point),
     Cut(Option<Entity>),
+    Delete(Option<Entity>),
     DesktopConfig(DesktopConfig),
     DesktopViewOptions,
     DialogCancel,
@@ -295,7 +296,6 @@ pub enum Message {
     LaunchUrl(String),
     MaybeExit,
     Modifiers(Modifiers),
-    MoveToTrash(Option<Entity>),
     MounterItems(MounterKey, MounterItems),
     MountResult(MounterKey, MounterItem, Result<bool, String>),
     NavBarClose(Entity),
@@ -1966,6 +1966,39 @@ impl Application for App {
                     }
                 }
             }
+            Message::Delete(entity_opt) => {
+                let entity = entity_opt.unwrap_or_else(|| self.tab_model.active());
+                if let Some(tab) = self.tab_model.data::<Tab>(entity) {
+                    match &tab.location {
+                        Location::Trash => {
+                            if let Some(items) = tab.items_opt() {
+                                let mut trash_items = Vec::new();
+                                for item in items.iter() {
+                                    if item.selected {
+                                        match &item.metadata {
+                                            ItemMetadata::Trash { entry, .. } => {
+                                                trash_items.push(entry.clone());
+                                            }
+                                            _ => {
+                                                //TODO: error on trying to permanently delete non-trash file?
+                                            }
+                                        }
+                                    }
+                                }
+                                if !trash_items.is_empty() {
+                                    self.operation(Operation::DeleteTrash { items: trash_items });
+                                }
+                            }
+                        }
+                        _ => {
+                            let paths = dbg!(self.selected_paths(entity_opt));
+                            if !paths.is_empty() {
+                                self.operation(Operation::Delete { paths });
+                            }
+                        }
+                    }
+                }
+            }
             Message::DesktopConfig(config) => {
                 if config != self.config.desktop {
                     config_set!(desktop, config);
@@ -2177,12 +2210,6 @@ impl Application for App {
             Message::Modifiers(modifiers) => {
                 self.modifiers = modifiers;
             }
-            Message::MoveToTrash(entity_opt) => {
-                let paths = self.selected_paths(entity_opt);
-                if !paths.is_empty() {
-                    self.operation(Operation::Delete { paths });
-                }
-            }
             Message::MounterItems(mounter_key, mounter_items) => {
                 // Check for unmounted folders
                 let mut unmounted = Vec::new();
@@ -2972,6 +2999,9 @@ impl Application for App {
                                 self.update_tab(entity, tab_path, selection_paths),
                             ]));
                         }
+                        tab::Command::Delete(paths) => {
+                            self.operation(Operation::Delete { paths });
+                        }
                         tab::Command::DropFiles(to, from) => {
                             commands.push(self.update(Message::PasteContents(to, from)));
                         }
@@ -2989,9 +3019,6 @@ impl Application for App {
                                 }),
                             );
                         }
-                        tab::Command::MoveToTrash(paths) => {
-                            self.operation(Operation::Delete { paths });
-                        }
                         tab::Command::OpenFile(path) => self.open_file(&path),
                         tab::Command::OpenInNewTab(path) => {
                             commands.push(self.open_tab(Location::Path(path.clone()), false, None));
diff --git a/src/key_bind.rs b/src/key_bind.rs
index 164a8c1..2a60495 100644
--- a/src/key_bind.rs
+++ b/src/key_bind.rs
@@ -64,7 +64,7 @@ pub fn key_binds(mode: &tab::Mode) -> HashMap<KeyBind, Action> {
     if matches!(mode, tab::Mode::App | tab::Mode::Desktop) {
         bind!([Ctrl], Key::Character("c".into()), Copy);
         bind!([Ctrl], Key::Character("x".into()), Cut);
-        bind!([], Key::Named(Named::Delete), MoveToTrash);
+        bind!([], Key::Named(Named::Delete), Delete);
         bind!([Shift], Key::Named(Named::Enter), OpenInNewWindow);
         bind!([Ctrl], Key::Character("v".into()), Paste);
         bind!([], Key::Named(Named::F2), Rename);
diff --git a/src/menu.rs b/src/menu.rs
index c65b26e..dfd59db 100644
--- a/src/menu.rs
+++ b/src/menu.rs
@@ -151,7 +151,7 @@ pub fn context_menu<'a>(
                 children.push(menu_item(fl!("cut"), Action::Cut).into());
                 children.push(menu_item(fl!("copy"), Action::Copy).into());
                 // Should this simply bypass trash and remove the shortcut?
-                children.push(menu_item(fl!("move-to-trash"), Action::MoveToTrash).into());
+                children.push(menu_item(fl!("move-to-trash"), Action::Delete).into());
             } else if selected > 0 {
                 if selected_dir == 1 && selected == 1 || selected_dir == 0 {
                     children.push(menu_item(fl!("open"), Action::Open).into());
@@ -211,7 +211,7 @@ pub fn context_menu<'a>(
                     children.push(menu_item(fl!("add-to-sidebar"), Action::AddToSidebar).into());
                 }
                 children.push(divider::horizontal::light().into());
-                children.push(menu_item(fl!("move-to-trash"), Action::MoveToTrash).into());
+                children.push(menu_item(fl!("move-to-trash"), Action::Delete).into());
             } else {
                 //TODO: need better designs for menu with no selection
                 //TODO: have things like properties but they apply to the folder?
@@ -311,6 +311,8 @@ pub fn context_menu<'a>(
                 children.push(divider::horizontal::light().into());
                 children
                     .push(menu_item(fl!("restore-from-trash"), Action::RestoreFromTrash).into());
+                children.push(divider::horizontal::light().into());
+                children.push(menu_item(fl!("delete-permanently"), Action::Delete).into());
             } else {
                 // TODO: Nested menu
                 children.push(sort_item(fl!("sort-by-name"), HeadingOptions::Name));
@@ -537,7 +539,15 @@ pub fn menu_bar<'a>(
                     menu::Item::Divider,
                     menu_button_optional(fl!("add-to-sidebar"), Action::AddToSidebar, selected > 0),
                     menu::Item::Divider,
-                    menu_button_optional(fl!("move-to-trash"), Action::MoveToTrash, selected > 0),
+                    menu_button_optional(
+                        if in_trash {
+                            fl!("delete-permanently")
+                        } else {
+                            fl!("move-to-trash")
+                        },
+                        Action::Delete,
+                        selected > 0,
+                    ),
                     menu::Item::Divider,
                     menu::Item::Button(fl!("close-tab"), None, Action::TabClose),
                     menu::Item::Button(fl!("quit"), None, Action::WindowClose),
diff --git a/src/operation/mod.rs b/src/operation/mod.rs
index 43adf07..68026e7 100644
--- a/src/operation/mod.rs
+++ b/src/operation/mod.rs
@@ -460,6 +460,10 @@ pub enum Operation {
     Delete {
         paths: Vec<PathBuf>,
     },
+    /// Delete a path from the trash
+    DeleteTrash {
+        items: Vec<trash::TrashItem>,
+    },
     /// Empty the trash
     EmptyTrash,
     /// Uncompress files
@@ -550,6 +554,9 @@ impl Operation {
                 to = fl!("trash"),
                 progress = progress()
             ),
+            Self::DeleteTrash { items } => {
+                fl!("deleting", items = items.len(), progress = progress())
+            }
             Self::EmptyTrash => fl!("emptying-trash", progress = progress()),
             Self::Extract {
                 paths,
@@ -609,6 +616,7 @@ impl Operation {
                 from = paths_parent_name(paths),
                 to = fl!("trash")
             ),
+            Self::DeleteTrash { items } => fl!("deleted", items = items.len()),
             Self::EmptyTrash => fl!("emptied-trash"),
             Self::Extract {
                 paths,
@@ -650,6 +658,7 @@ impl Operation {
             Self::Compress { .. }
             | Self::Copy { .. }
             | Self::Delete { .. }
+            | Self::DeleteTrash { .. }
             | Self::EmptyTrash
             | Self::Extract { .. }
             | Self::Move { .. }
@@ -846,6 +855,34 @@ impl Operation {
                 }
                 Ok(OperationSelection::default())
             }
+            Self::DeleteTrash { items } => {
+                #[cfg(any(
+                    target_os = "windows",
+                    all(
+                        unix,
+                        not(target_os = "macos"),
+                        not(target_os = "ios"),
+                        not(target_os = "android")
+                    )
+                ))]
+                {
+                    tokio::task::spawn_blocking(move || -> Result<(), OperationError> {
+                        let count = items.len();
+                        for (i, item) in items.into_iter().enumerate() {
+                            controller.check().map_err(OperationError::from_str)?;
+
+                            controller.set_progress(i as f32 / count as f32);
+
+                            trash::os_limited::purge_all([item])
+                                .map_err(OperationError::from_str)?;
+                        }
+                        Ok(())
+                    })
+                    .await
+                    .map_err(OperationError::from_str)??;
+                }
+                Ok(OperationSelection::default())
+            }
             Self::EmptyTrash => {
                 #[cfg(any(
                     target_os = "windows",
diff --git a/src/tab.rs b/src/tab.rs
index 2b09f38..f6d3f58 100644
--- a/src/tab.rs
+++ b/src/tab.rs
@@ -1127,12 +1127,12 @@ pub enum Command {
     AddToSidebar(PathBuf),
     AutoScroll(Option<f32>),
     ChangeLocation(String, Location, Option<Vec<PathBuf>>),
+    Delete(Vec<PathBuf>),
     DropFiles(PathBuf, ClipboardPaste),
     EmptyTrash,
     #[cfg(feature = "desktop")]
     ExecEntryAction(cosmic::desktop::DesktopEntryData, usize),
     Iced(TaskWrapper),
-    MoveToTrash(Vec<PathBuf>),
     OpenFile(PathBuf),
     OpenInNewTab(PathBuf),
     OpenInNewWindow(PathBuf),
@@ -3188,7 +3188,7 @@ impl Tab {
                         commands.push(Command::DropFiles(to, from))
                     }
                     Location::Trash if matches!(from.kind, ClipboardKind::Cut) => {
-                        commands.push(Command::MoveToTrash(from.paths))
+                        commands.push(Command::Delete(from.paths))
                     }
                     _ => {
                         log::warn!("{:?} to {:?} is not supported.", from.kind, to);