diff --git a/app/assets/stylesheets/pageflow/editor/filtered_files.scss b/app/assets/stylesheets/pageflow/editor/filtered_files.scss
index 90726d2507..e1325b940e 100644
--- a/app/assets/stylesheets/pageflow/editor/filtered_files.scss
+++ b/app/assets/stylesheets/pageflow/editor/filtered_files.scss
@@ -112,12 +112,17 @@
     flex: 1;
   }
 
-  // On a line of its own, so that the number of checked files is not
-  // squeezed next to it in languages with longer words than English.
+  // On a line of their own, so that the number of checked files is not
+  // squeezed next to them in languages with longer words than English.
+  &-selection_bar_actions {
+    display: flex;
+    align-self: flex-end;
+    gap: space(1);
+  }
+
   &-selection_bar_action {
     @include simple-button;
 
-    align-self: flex-end;
     padding: space(1) space(4);
 
     &[disabled] {
@@ -126,6 +131,16 @@
     }
   }
 
+  // The icon only mixin brings its own vertical padding, which would
+  // make this button taller than the one next to it.
+  &-selection_bar_destroy {
+    @include icon-only-button("destructive");
+    @include trash-icon;
+
+    padding-top: space(1);
+    padding-bottom: space(1);
+  }
+
   &-selection_bar_dismiss {
     @include cancel-icon;
 
diff --git a/config/locales/de.yml b/config/locales/de.yml
index c8c77702ff..8f75ebff71 100644
--- a/config/locales/de.yml
+++ b/config/locales/de.yml
@@ -1535,6 +1535,8 @@ de:
         chapter_item_view:
           chapter: Kapitel
           unnamed: "(Unbenannt)"
+        confirmable_file_item_view:
+          confirm_destroy: Datei wirklich löschen?
         edit_chapter_view:
           confirm_destroy: |-
             Kapitel einschließlich ALLER enthaltener Seiten wirklich löschen?
@@ -1565,6 +1567,8 @@ de:
           show_editor: Editorleiste einblenden
         entry_preview_view:
           scroll_hint: Scrollen, um weiterzulesen
+        file_item_view:
+          confirm_destroy: Datei wirklich löschen?
         file_meta_data_item_value_view:
           blank: "-"
         file_preview_progress_bar_view:
@@ -1590,6 +1594,10 @@ de:
           actions: 'Aktionen für die Dateiliste'
           any_file_type: 'Datei'
           cancel_selection: 'Auswahl abbrechen'
+          confirm_destroy_selection:
+            one: '1 Element wirklich löschen?'
+            other: '%{count} Elemente wirklich löschen?'
+          destroy_selection: 'Auswahl löschen'
           end_selection: 'Auswahl beenden'
           move_selection: 'Verschieben...'
           reset_filter: 'Filter zurücksetzen'
diff --git a/config/locales/en.yml b/config/locales/en.yml
index 14672e825a..510f61afe9 100644
--- a/config/locales/en.yml
+++ b/config/locales/en.yml
@@ -1527,6 +1527,8 @@ en:
         chapter_item_view:
           chapter: Chapter
           unnamed: "(New chapter)"
+        confirmable_file_item_view:
+          confirm_destroy: Really delete this file?
         edit_chapter_view:
           confirm_destroy: |-
             Really delete this chapter including ALL its pages?
@@ -1557,6 +1559,8 @@ en:
           show_editor: Show editor panel
         entry_preview_view:
           scroll_hint: Scroll down to continue
+        file_item_view:
+          confirm_destroy: Really delete this file?
         file_meta_data_item_value_view:
           blank: "-"
         file_preview_progress_bar_view:
@@ -1582,6 +1586,10 @@ en:
           actions: 'File list actions'
           any_file_type: 'a file'
           cancel_selection: 'Cancel selection'
+          confirm_destroy_selection:
+            one: 'Really delete 1 item?'
+            other: 'Really delete %{count} items?'
+          destroy_selection: 'Delete selection'
           end_selection: 'End selection'
           move_selection: 'Move...'
           reset_filter: 'Reset filter'
diff --git a/package/spec/editor/collections/FileFoldersCollection-spec.js b/package/spec/editor/collections/FileFoldersCollection-spec.js
index 0ab7bfec87..1e26afb30a 100644
--- a/package/spec/editor/collections/FileFoldersCollection-spec.js
+++ b/package/spec/editor/collections/FileFoldersCollection-spec.js
@@ -1,3 +1,5 @@
+import Backbone from 'backbone';
+
 import {FileFoldersCollection} from 'pageflow/editor';
 
 import * as support from '$support';
@@ -159,6 +161,32 @@ describe('FileFoldersCollection', () => {
     });
   });
 
+  describe('#isEmptyFolder', () => {
+    it('returns true for folder without files or subfolders', () => {
+      const fileFolders = collection([{perma_id: 1, name: 'Interviews'}]);
+      const files = new Backbone.Collection([{folder_perma_id: 2}]);
+
+      expect(fileFolders.isEmptyFolder(fileFolders.byPermaId(1), files)).toBe(true);
+    });
+
+    it('returns false for folder which holds a file', () => {
+      const fileFolders = collection([{perma_id: 1, name: 'Interviews'}]);
+      const files = new Backbone.Collection([{folder_perma_id: 1}]);
+
+      expect(fileFolders.isEmptyFolder(fileFolders.byPermaId(1), files)).toBe(false);
+    });
+
+    it('returns false for folder which holds an empty subfolder', () => {
+      const fileFolders = collection([
+        {perma_id: 1, name: 'Interviews'},
+        {perma_id: 2, name: 'Raw', parent_folder_perma_id: 1}
+      ]);
+      const files = new Backbone.Collection([]);
+
+      expect(fileFolders.isEmptyFolder(fileFolders.byPermaId(1), files)).toBe(false);
+    });
+  });
+
   describe('persistence', () => {
     support.useFakeXhr(() => testContext);
 
diff --git a/package/spec/editor/collections/ListSelection-spec.js b/package/spec/editor/collections/ListSelection-spec.js
index 9a97cbecf1..0d3bd5f450 100644
--- a/package/spec/editor/collections/ListSelection-spec.js
+++ b/package/spec/editor/collections/ListSelection-spec.js
@@ -46,4 +46,31 @@ describe('ListSelection', () => {
 
     expect(selection.models).toEqual([file]);
   });
+
+  describe('#destroyAll', () => {
+    it('destroys every selected item', () => {
+      const file = f.file({id: 1});
+      const otherFile = f.file({id: 2});
+      jest.spyOn(file, 'destroy').mockImplementation(() => {});
+      jest.spyOn(otherFile, 'destroy').mockImplementation(() => {});
+      const selection = new ListSelection([file, otherFile]);
+
+      selection.destroyAll();
+
+      expect(file.destroy).toHaveBeenCalled();
+      expect(otherFile.destroy).toHaveBeenCalled();
+    });
+
+    it('destroys items which leave the selection along the way', () => {
+      const file = f.file({id: 1});
+      const otherFile = f.file({id: 2});
+      const selection = new ListSelection([file, otherFile]);
+      jest.spyOn(file, 'destroy').mockImplementation(() => selection.remove(file));
+      jest.spyOn(otherFile, 'destroy').mockImplementation(() => selection.remove(otherFile));
+
+      selection.destroyAll();
+
+      expect(otherFile.destroy).toHaveBeenCalled();
+    });
+  });
 });
diff --git a/package/spec/editor/models/DestroyMenuItem-spec.js b/package/spec/editor/models/DestroyMenuItem-spec.js
index 255467a86b..501ec90bfb 100644
--- a/package/spec/editor/models/DestroyMenuItem-spec.js
+++ b/package/spec/editor/models/DestroyMenuItem-spec.js
@@ -3,8 +3,8 @@ import {useFakeTranslations} from 'pageflow/testHelpers';
 
 describe('DestroyMenuItem', () => {
   useFakeTranslations({
-    'pageflow.editor.destroy_menu_item.destroy': 'Delete',
-    'pageflow.editor.destroy_menu_item.confirm_destroy': 'Really delete?'
+    'pageflow.editor.views.destroy_menu_item.destroy': 'Delete',
+    'pageflow.editor.views.destroy_menu_item.confirm_destroy': 'Really delete?'
   });
 
   it('has name destroy by default', () => {
diff --git a/package/spec/editor/views/ConfirmableFileItemView-spec.js b/package/spec/editor/views/ConfirmableFileItemView-spec.js
index b06f8187c6..1086328de4 100644
--- a/package/spec/editor/views/ConfirmableFileItemView-spec.js
+++ b/package/spec/editor/views/ConfirmableFileItemView-spec.js
@@ -4,6 +4,11 @@ import * as support from '$support';
 import {renderBackboneView as render} from 'pageflow/testHelpers';
 
 describe('ConfirmableFileItemView', () => {
+  support.useFakeTranslations({
+    'pageflow.editor.templates.confirmable_file_item.remove': 'Delete',
+    'pageflow.editor.views.confirmable_file_item_view.confirm_destroy': 'Really delete this file?'
+  });
+
   it('displays file title', () => {
     const file = support.factories.file({file_name: 'original.mp4'});
 
@@ -16,4 +21,37 @@ describe('ConfirmableFileItemView', () => {
 
     expect(getByText('original.mp4')).not.toBeNull();
   });
+
+  it('destroys file when delete is clicked', () => {
+    window.confirm = jest.fn(() => true);
+    const file = support.factories.file({file_name: 'original.mp4'});
+    jest.spyOn(file, 'destroy').mockImplementation(() => {});
+
+    const view = new ConfirmableFileItemView({
+      model: file,
+      selectedFiles: new Backbone.Collection()
+    });
+
+    const {getByTitle} = render(view);
+    getByTitle('Delete').click();
+
+    expect(window.confirm).toHaveBeenCalledWith('Really delete this file?');
+    expect(file.destroy).toHaveBeenCalled();
+  });
+
+  it('keeps file when the confirmation is dismissed', () => {
+    window.confirm = jest.fn(() => false);
+    const file = support.factories.file({file_name: 'original.mp4'});
+    jest.spyOn(file, 'destroy').mockImplementation(() => {});
+
+    const view = new ConfirmableFileItemView({
+      model: file,
+      selectedFiles: new Backbone.Collection()
+    });
+
+    const {getByTitle} = render(view);
+    getByTitle('Delete').click();
+
+    expect(file.destroy).not.toHaveBeenCalled();
+  });
 });
diff --git a/package/spec/editor/views/FileItemView-spec.js b/package/spec/editor/views/FileItemView-spec.js
index 41b1eb6713..8c69c10238 100644
--- a/package/spec/editor/views/FileItemView-spec.js
+++ b/package/spec/editor/views/FileItemView-spec.js
@@ -22,7 +22,8 @@ describe('FileItemView', () => {
     'pageflow.editor.templates.file_item.move': 'Move...',
     'pageflow.editor.templates.file_item.settings': 'Settings',
     'pageflow.editor.templates.file_item.select': 'Select',
-    'pageflow.editor.templates.files.in_folder': 'In folder:'
+    'pageflow.editor.templates.files.in_folder': 'In folder:',
+    'pageflow.editor.views.file_item_view.confirm_destroy': 'Really delete this file?'
   });
 
   it('displays file title', () => {
@@ -406,9 +407,23 @@ describe('FileItemView', () => {
       const {getByRole} = render(view);
       getByRole('link', {name: 'Delete'}).click();
 
+      expect(window.confirm).toHaveBeenCalledWith('Really delete this file?');
       expect(file.destroy).toHaveBeenCalled();
     });
 
+    it('keeps file when the confirmation is dismissed', () => {
+      window.confirm = jest.fn(() => false);
+      const file = support.factories.file({id: 123});
+      jest.spyOn(file, 'destroy').mockImplementation(() => {});
+
+      const view = new FileItemView({model: file});
+
+      const {getByRole} = render(view);
+      getByRole('link', {name: 'Delete'}).click();
+
+      expect(file.destroy).not.toHaveBeenCalled();
+    });
+
     it('cancels upload when cancel upload is selected', () => {
       const file = support.factories.file({id: 123, state: 'uploading'});
       jest.spyOn(file, 'cancelUpload').mockImplementation(() => {});
diff --git a/package/spec/editor/views/FilesView-spec.js b/package/spec/editor/views/FilesView-spec.js
index a3a3a4a9fb..4e0bcbf2bc 100644
--- a/package/spec/editor/views/FilesView-spec.js
+++ b/package/spec/editor/views/FilesView-spec.js
@@ -77,6 +77,11 @@ describe('FilesView', () => {
     'pageflow.editor.views.filtered_files_view.actions': 'File list actions',
     'pageflow.editor.views.filtered_files_view.select_items': 'Select files and folders',
     'pageflow.editor.views.filtered_files_view.end_selection': 'End selection',
+    'pageflow.editor.views.filtered_files_view.destroy_selection': 'Delete selection',
+    'pageflow.editor.views.filtered_files_view.confirm_destroy_selection': {
+      one: 'Really delete 1 item?',
+      other: 'Really delete %{count} items?'
+    },
     'pageflow.editor.views.filtered_files_view.selected_items': {
       zero: 'No items selected',
       one: '1 item selected',
@@ -1322,6 +1327,10 @@ describe('FilesView', () => {
         return view.el.querySelector('.filtered_files-selection_bar');
       }
 
+      function destroyButton(queries) {
+        return queries.getByRole('button', {name: 'Delete selection'});
+      }
+
       it('does not show check boxes before selecting has started', () => {
         const view = new FilesView({model: entryWithFolders()});
 
@@ -1447,6 +1456,62 @@ describe('FilesView', () => {
 
         expect(queryByRole('checkbox', {name: /^Interviews/})).toBeNull();
       });
+
+      it('deletes checked folders and files at once', async () => {
+        const entry = entryWithFolders();
+        const view = new FilesView({model: entry});
+        const user = userEvent.setup();
+        window.confirm = jest.fn(() => true);
+
+        const queries = render(view);
+        await startSelecting(user, queries);
+        await check(user, queries, /^Landscapes/);
+        await check(user, queries, 'unfiled.png');
+        await user.click(destroyButton(queries));
+
+        expect(window.confirm).toHaveBeenCalledWith('Really delete 2 items?');
+        expect(testContext.requests.map(request => request.url))
+          .toEqual(['/editor/entries/1/file_folders/12',
+                    '/editor/entries/1/files/image_files/1']);
+      });
+
+      it('is not offered for a folder which still holds files', async () => {
+        const view = new FilesView({model: entryWithFolders(), folderPermaId: '1'});
+        const user = userEvent.setup();
+
+        const queries = render(view);
+        await startSelecting(user, queries);
+        await check(user, queries, /^Raw/);
+
+        expect(destroyButton(queries)).toBeDisabled();
+      });
+
+      it('is not offered for a folder which still holds subfolders', async () => {
+        const view = new FilesView({model: entryWithFolders()});
+        const user = userEvent.setup();
+
+        const queries = render(view);
+        await startSelecting(user, queries);
+        await check(user, queries, /^Interviews/);
+
+        expect(destroyButton(queries)).toBeDisabled();
+      });
+
+      it('is offered again once the non-empty folder is unchecked', async () => {
+        const view = new FilesView({model: entryWithFolders()});
+        const user = userEvent.setup();
+
+        const queries = render(view);
+        await startSelecting(user, queries);
+        await check(user, queries, /^Landscapes/);
+        await check(user, queries, /^Interviews/);
+
+        expect(destroyButton(queries)).toBeDisabled();
+
+        await check(user, queries, /^Interviews/);
+
+        expect(destroyButton(queries)).toBeEnabled();
+      });
     });
 
     describe('filtering by file type', () => {
diff --git a/package/spec/editor/views/FilteredFilesView-spec.js b/package/spec/editor/views/FilteredFilesView-spec.js
index 0c51f5ee84..d5f0bc828f 100644
--- a/package/spec/editor/views/FilteredFilesView-spec.js
+++ b/package/spec/editor/views/FilteredFilesView-spec.js
@@ -24,6 +24,11 @@ describe('FilteredFilesView', () => {
     'pageflow.editor.views.filtered_files_view.actions': 'File list actions',
     'pageflow.editor.views.filtered_files_view.select_items': 'Select files and folders',
     'pageflow.editor.views.filtered_files_view.end_selection': 'End selection',
+    'pageflow.editor.views.filtered_files_view.destroy_selection': 'Delete selection',
+    'pageflow.editor.views.filtered_files_view.confirm_destroy_selection': {
+      one: 'Really delete 1 item?',
+      other: 'Really delete %{count} items?'
+    },
     'pageflow.editor.views.filtered_files_view.selected_items': {
       zero: 'No items selected',
       one: '1 item selected',
@@ -737,6 +742,76 @@ describe('FilteredFilesView', () => {
       expect(queries.getByRole('link', {name: 'Alphabetical'})).not.toBeNull();
       expect(view.el.querySelector('.drop_down_button_item .label')).toHaveTextContent('Sort');
     });
+
+    describe('deleting the selection', () => {
+      let testContext;
+
+      beforeEach(() => {
+        testContext = {};
+      });
+
+      support.useFakeXhr(() => testContext);
+
+      function destroyButton(queries) {
+        return queries.getByRole('button', {name: 'Delete selection'});
+      }
+
+      it('deletes all checked files once the confirmation is accepted', async () => {
+        const {entry, queries} = setup();
+        const user = userEvent.setup();
+        window.confirm = jest.fn(() => true);
+
+        await startSelecting(user, queries);
+        await user.click(checkBoxFor(queries, 'image.png'));
+        await user.click(checkBoxFor(queries, 'photo.png'));
+        await user.click(destroyButton(queries));
+
+        expect(window.confirm).toHaveBeenCalledWith('Really delete 2 items?');
+        expect(testContext.requests.map(request => request.method)).toEqual(['DELETE', 'DELETE']);
+        expect(entry.getFileCollection('image_files').length).toEqual(0);
+      });
+
+      it('keeps the files when the confirmation is dismissed', async () => {
+        const {view, entry, queries} = setup();
+        const user = userEvent.setup();
+        window.confirm = jest.fn(() => false);
+
+        await startSelecting(user, queries);
+        await user.click(checkBoxFor(queries, 'image.png'));
+        await user.click(destroyButton(queries));
+
+        expect(testContext.requests).toEqual([]);
+        expect(entry.getFileCollection('image_files').length).toEqual(2);
+        expect(list(view)).toHaveClass('is_selecting');
+        expect(selectionBar(view)).toHaveTextContent('1 item selected');
+      });
+
+      it('stops checking files once they have been deleted', async () => {
+        const {view, queries} = setup();
+        const user = userEvent.setup();
+        window.confirm = jest.fn(() => true);
+
+        await startSelecting(user, queries);
+        await user.click(checkBoxFor(queries, 'image.png'));
+        await user.click(destroyButton(queries));
+
+        expect(list(view)).not.toHaveClass('is_selecting');
+        expect(selectionBar(view)).toHaveTextContent('No items selected');
+      });
+
+      it('is not offered while nothing is checked', async () => {
+        const {queries} = setup();
+        const user = userEvent.setup();
+
+        await startSelecting(user, queries);
+
+        expect(destroyButton(queries)).toBeDisabled();
+
+        await user.click(checkBoxFor(queries, 'image.png'));
+
+        expect(destroyButton(queries)).toBeEnabled();
+      });
+    });
   });
 
   describe('banner', () => {
diff --git a/package/src/editor/collections/FileFoldersCollection.js b/package/src/editor/collections/FileFoldersCollection.js
index 56337d0862..82f1af1510 100644
--- a/package/src/editor/collections/FileFoldersCollection.js
+++ b/package/src/editor/collections/FileFoldersCollection.js
@@ -64,6 +64,17 @@ export const FileFoldersCollection = Backbone.Collection.extend({
     });
   },
 
+  // The server refuses to delete a folder which still holds files or
+  // subfolders, empty subfolders included.
+  isEmptyFolder: function(folder, files) {
+    var permaId = folder.get('perma_id');
+
+    return !this.childrenOf(folder).length &&
+           !files.some(function(file) {
+             return file.get('folder_perma_id') === permaId;
+           });
+  },
+
   descendantPermaIdsOf: function(folder) {
     return this.collectDescendantPermaIds(folder, []);
   },
diff --git a/package/src/editor/collections/ListSelection.js b/package/src/editor/collections/ListSelection.js
index 035e613736..6434e6cf09 100644
--- a/package/src/editor/collections/ListSelection.js
+++ b/package/src/editor/collections/ListSelection.js
@@ -34,5 +34,13 @@ export const ListSelection = Backbone.Collection.extend({
 
   includes: function(item) {
     return !!this.get(item);
+  },
+
+  // Iterating a copy since destroying an item takes it out of the list,
+  // which drops it from the selection and would skip the item behind it.
+  destroyAll: function() {
+    this.models.slice().forEach(function(item) {
+      item.destroy();
+    });
   }
 });
diff --git a/package/src/editor/models/DestroyMenuItem.js b/package/src/editor/models/DestroyMenuItem.js
index 83256c9fea..64826cf4da 100644
--- a/package/src/editor/models/DestroyMenuItem.js
+++ b/package/src/editor/models/DestroyMenuItem.js
@@ -18,7 +18,7 @@ import I18n from 'i18n-js';
  * @since edge
  */
 export const DestroyMenuItem = Backbone.Model.extend({
-  translationKeyPrefix: 'pageflow.editor.destroy_menu_item',
+  translationKeyPrefix: 'pageflow.editor.views.destroy_menu_item',
 
   defaults: {
     name: 'destroy',
diff --git a/package/src/editor/templates/filteredFiles.jst b/package/src/editor/templates/filteredFiles.jst
index ff85d1b0e8..725fc6f3e4 100644
--- a/package/src/editor/templates/filteredFiles.jst
+++ b/package/src/editor/templates/filteredFiles.jst
@@ -14,7 +14,10 @@
       <button type="button" class="filtered_files-selection_bar_dismiss"></button>
     </div>
 
-    <button type="button" class="filtered_files-selection_bar_action"></button>
+    <div class="filtered_files-selection_bar_actions">
+      <button type="button" class="filtered_files-selection_bar_action"></button>
+      <button type="button" class="filtered_files-selection_bar_destroy"></button>
+    </div>
   </div>
 </div>
 <div class="filtered_files-list"></div>
diff --git a/package/src/editor/views/ConfirmableFileItemView.js b/package/src/editor/views/ConfirmableFileItemView.js
index d39c611426..25cc6aa023 100644
--- a/package/src/editor/views/ConfirmableFileItemView.js
+++ b/package/src/editor/views/ConfirmableFileItemView.js
@@ -1,4 +1,5 @@
 import Marionette from 'backbone.marionette';
+import I18n from 'i18n-js';
 
 import template from '../templates/confirmableFileItem.jst';
 
@@ -31,7 +32,7 @@ export const ConfirmableFileItemView = Marionette.ItemView.extend({
   },
 
   destroy: function() {
-    if (confirm("Datei wirklich wirklich löschen?")) {
+    if (window.confirm(I18n.t('pageflow.editor.views.confirmable_file_item_view.confirm_destroy'))) {
       this.model.destroy();
     }
   },
diff --git a/package/src/editor/views/FileItemView.js b/package/src/editor/views/FileItemView.js
index 6253d12904..f367656074 100644
--- a/package/src/editor/views/FileItemView.js
+++ b/package/src/editor/views/FileItemView.js
@@ -303,7 +303,7 @@ export const FileItemView = Marionette.ItemView.extend({
   },
 
   destroy: function() {
-    if (confirm("Datei wirklich wirklich löschen?")) {
+    if (window.confirm(I18n.t('pageflow.editor.views.file_item_view.confirm_destroy'))) {
       this.model.destroy();
     }
   },
diff --git a/package/src/editor/views/FilteredFilesView.js b/package/src/editor/views/FilteredFilesView.js
index 9526d491bf..97d3110a9c 100644
--- a/package/src/editor/views/FilteredFilesView.js
+++ b/package/src/editor/views/FilteredFilesView.js
@@ -16,6 +16,7 @@ import {FilesBlankSlateView} from './FilesBlankSlateView';
 import {FilesListItemView} from './FilesListItemView';
 import {FileTypePillsView} from './FileTypePillsView';
 import {FolderBreadcrumbView} from './FolderBreadcrumbView';
+import {FileFolder} from '../models/FileFolder';
 import {Search} from '../models/Search';
 import {ListHighlight} from '../models/ListHighlight';
 import {ListSearchFieldView} from './ListSearchFieldView';
@@ -37,6 +38,7 @@ export const FilteredFilesView = Marionette.ItemView.extend({
     selectionBar: '.filtered_files-selection_bar',
     selectionBarText: '.filtered_files-selection_bar_text',
     selectionBarAction: '.filtered_files-selection_bar_action',
+    selectionBarDestroy: '.filtered_files-selection_bar_destroy',
     selectionBarDismiss: '.filtered_files-selection_bar_dismiss',
     list: '.filtered_files-list',
     sort: '.filtered_files-sort',
@@ -51,8 +53,8 @@ export const FilteredFilesView = Marionette.ItemView.extend({
       return false;
     },
 
-    // Moving is all a selection is good for so far, so the check boxes
-    // go away again once the files have been moved.
+    // Each bulk action is the point of the selection it acts on, so the
+    // check boxes go away again once one of them has run.
     'click .filtered_files-selection_bar_action': function() {
       MoveToFolderDialogView.open({
         models: this.listSelection.models,
@@ -63,6 +65,11 @@ export const FilteredFilesView = Marionette.ItemView.extend({
       return false;
     },
 
+    'click .filtered_files-selection_bar_destroy': function() {
+      this.destroySelection();
+      return false;
+    },
+
     'click .filtered_files-selection_bar_dismiss': function() {
       this.stopSelecting();
       return false;
@@ -308,6 +315,18 @@ export const FilteredFilesView = Marionette.ItemView.extend({
     this.listSelection.stop();
   },
 
+  destroySelection: function() {
+    var message = this.translation('confirm_destroy_selection',
+                                   {count: this.listSelection.length});
+
+    if (!window.confirm(message)) {
+      return;
+    }
+
+    this.listSelection.destroyAll();
+    this.stopSelecting();
+  },
+
   updateSelecting: function() {
     if (!this.listSelection) {
       return this.ui.selectionBar.remove();
@@ -320,12 +339,14 @@ export const FilteredFilesView = Marionette.ItemView.extend({
     this.collectionView.$el.toggleClass('is_selecting', selecting);
 
     var dismissLabel = this.translation('end_selection');
+    var destroyLabel = this.translation('destroy_selection');
 
     this.ui.selectionBarDismiss.attr({title: dismissLabel, 'aria-label': dismissLabel});
     this.ui.selectionBarAction.text(this.translation('move_selection'));
+    this.ui.selectionBarDestroy.attr({title: destroyLabel, 'aria-label': destroyLabel});
 
     // Files can only be moved into folders, so entries which have none
-    // offer nothing to do with a selection yet.
+    // offer nothing to move a selection into.
     this.ui.selectionBarAction.toggle(!!this.options.fileFolders);
 
     this.updateSelectionBar();
@@ -355,6 +376,17 @@ export const FilteredFilesView = Marionette.ItemView.extend({
                                                    {count: this.listSelection.length}));
 
     this.ui.selectionBarAction.prop('disabled', !this.listSelection.length);
+    this.ui.selectionBarDestroy.prop('disabled', !this.listSelection.length ||
+                                                 this.selectionContainsNonEmptyFolder());
+  },
+
+  selectionContainsNonEmptyFolder: function() {
+    var files = this.selectedFiles || this.combinedFiles;
+
+    return this.listSelection.some(function(model) {
+      return model instanceof FileFolder &&
+             !this.options.fileFolders.isEmptyFolder(model, files);
+    }, this);
   },
 
   translation: function(keyName, options) {
diff --git a/package/src/editor/views/FolderItemView.js b/package/src/editor/views/FolderItemView.js
index 57612c2f8f..7c1e56913e 100644
--- a/package/src/editor/views/FolderItemView.js
+++ b/package/src/editor/views/FolderItemView.js
@@ -132,16 +132,10 @@ export const FolderItemView = Marionette.ItemView.extend({
     this.menuItems.findWhere({name: 'move'}).set('hidden', !movable);
   },
 
-  // The server refuses to delete a folder which still holds files or
-  // subfolders. Files hidden by the file type filter cannot make one
-  // look empty, since such a folder is not listed to begin with.
+  // Files hidden by the file type filter cannot make a folder look
+  // empty, since such a folder is not listed to begin with.
   updateDestroyItem: function() {
-    var permaId = this.model.get('perma_id');
-
-    var empty = !this.options.fileFolders.childrenOf(this.model).length &&
-                !this.options.files.some(function(file) {
-                  return file.get('folder_perma_id') === permaId;
-                });
+    var empty = this.options.fileFolders.isEmptyFolder(this.model, this.options.files);
 
     this.menuItems.findWhere({name: 'destroy'}).set('hidden', !empty);
   },