diff --git a/src/calibre/gui2/viewer/toolbars.py b/src/calibre/gui2/viewer/toolbars.py
index 5455953c77..243108f4f5 100644
--- a/src/calibre/gui2/viewer/toolbars.py
+++ b/src/calibre/gui2/viewer/toolbars.py
@@ -306,10 +306,13 @@ class ActionsToolBar(ToolBar):
                     continue
                 if hasattr(set_book_path, 'pathtoebook') and path == os.path.abspath(set_book_path.pathtoebook):
                     continue
-                m.addAction('{}\t {}'.format(
-                    elided_text(entry['title'], pos='right', width=250),
-                    elided_text(os.path.basename(path), width=250))).triggered.connect(partial(
-                    self.open_book_at_path.emit, path))
+                if os.path.exists(path):
+                    m.addAction('{}\t {}'.format(
+                        elided_text(entry['title'], pos='right', width=250),
+                        elided_text(os.path.basename(path), width=250))).triggered.connect(partial(
+                        self.open_book_at_path.emit, path))
+                else:
+                    self.web_view.remove_recently_opened(path)
 
     def on_view_created(self, data):
         self.default_color_schemes = data['default_color_schemes']
diff --git a/src/calibre/gui2/viewer/ui.py b/src/calibre/gui2/viewer/ui.py
index 23b0cd94bf..6783bcb6c8 100644
--- a/src/calibre/gui2/viewer/ui.py
+++ b/src/calibre/gui2/viewer/ui.py
@@ -178,7 +178,7 @@ class EbookViewer(MainWindow):
         self.web_view.quit.connect(self.quit)
         self.web_view.update_current_toc_nodes.connect(self.toc.update_current_toc_nodes)
         self.web_view.toggle_full_screen.connect(self.toggle_full_screen)
-        self.web_view.ask_for_open.connect(self.ask_for_open, type=Qt.ConnectionType.QueuedConnection)
+        self.web_view.ask_for_open.connect(self.ask_for_open_from_js, type=Qt.ConnectionType.QueuedConnection)
         self.web_view.selection_changed.connect(self.lookup_widget.selected_text_changed, type=Qt.ConnectionType.QueuedConnection)
         self.web_view.selection_changed.connect(self.highlights_widget.selected_text_changed, type=Qt.ConnectionType.QueuedConnection)
         self.web_view.view_image.connect(self.view_image, type=Qt.ConnectionType.QueuedConnection)
@@ -452,6 +452,14 @@ class EbookViewer(MainWindow):
             self.removeToolBar(toolbar)
             self.addToolBar(Qt.ToolBarArea.LeftToolBarArea, toolbar)
 
+    def ask_for_open_from_js(self, path):
+        if path and not os.path.exists(path):
+            self.web_view.remove_recently_opened(path)
+            error_dialog(self, _('Book does not exist'), _(
+                'Cannot open {} as it no longer exists').format(path), show=True)
+        else:
+            self.ask_for_open(path)
+
     def ask_for_open(self, path=None):
         if path is None:
             files = choose_files(
diff --git a/src/calibre/gui2/viewer/web_view.py b/src/calibre/gui2/viewer/web_view.py
index 4bff7f438e..6e83ba63cc 100644
--- a/src/calibre/gui2/viewer/web_view.py
+++ b/src/calibre/gui2/viewer/web_view.py
@@ -753,3 +753,6 @@ class WebView(RestartingWebEngineView):
 
     def repair_after_fullscreen_switch(self):
         self.execute_when_ready('repair_after_fullscreen_switch')
+
+    def remove_recently_opened(self, path):
+        self.generic_action('remove-recently-opened', {'path': path})
diff --git a/src/pyj/read_book/open_book.pyj b/src/pyj/read_book/open_book.pyj
index 33cff6e34b..26b5025a66 100644
--- a/src/pyj/read_book/open_book.pyj
+++ b/src/pyj/read_book/open_book.pyj
@@ -3,29 +3,42 @@
 from __python__ import bound_methods, hash_literals
 
 from elementmaker import E
-from gettext import gettext as _
 
 from book_list.globals import get_session_data
 from book_list.item_list import create_item, create_item_list
-from dom import unique_id
+from dom import clear, unique_id
+from gettext import gettext as _
 from read_book.globals import ui_operations
 from widgets import create_button
 
+current_container_id = None
+current_opened_book_path = None
+
 
 def create_open_book(container, book):
-    container.appendChild(E.div(style='margin: 1rem'))
+    nonlocal current_container_id, current_opened_book_path
+    container.appendChild(E.div(style='margin: 1rem', id=unique_id()))
     container = container.lastChild
+    current_container_id = container.id
+    current_opened_book_path = None
+    if book:
+        current_opened_book_path = book.manifest.pathtoebook
+    rebuild_open_list(container)
+
+
+def rebuild_open_list(container):
+    clear(container)
     container.appendChild(create_button(_('Open a book from your computer'), action=ui_operations.ask_for_open.bind(None, None)))
     sd = get_session_data()
     rl = sd.get('standalone_recently_opened')
-    if rl.length:
+    if rl?.length:
         container.appendChild(E.div(id=unique_id()))
         c = container.lastChild
         items = []
         c.appendChild(E.h2(style='margin-top: 1rem', _('Recently viewed books')))
         c.appendChild(E.div())
         for entry in rl:
-            if book and book.manifest.pathtoebook is entry.pathtoebook:
+            if current_opened_book_path and current_opened_book_path is entry.pathtoebook:
                 continue
             if jstype(entry.pathtoebook) is not 'string':
                 continue
@@ -62,3 +75,17 @@ def add_book_to_recently_viewed(book):
             ans.push(entry)
     sd.set('standalone_recently_opened', ans.slice(0, 25))
     return ans
+
+
+def remove_recently_opened(path):
+    sd = get_session_data()
+    rl = sd.get('standalone_recently_opened')
+    newl = v'[]'
+    for entry in rl:
+        if entry.key is not path:
+            newl.push(entry)
+    sd.set('standalone_recently_opened', newl)
+    if current_container_id:
+        container = document.getElementById(current_container_id)
+        if container:
+            rebuild_open_list(container)
diff --git a/src/pyj/viewer-main.pyj b/src/pyj/viewer-main.pyj
index 30aecaeff4..b447d95d50 100644
--- a/src/pyj/viewer-main.pyj
+++ b/src/pyj/viewer-main.pyj
@@ -2,25 +2,28 @@
 # License: GPL v3 Copyright: 2018, Kovid Goyal <kovid at kovidgoyal.net>
 from __python__ import bound_methods, hash_literals
 
-import traceback
 from elementmaker import E
-from gettext import gettext as _, install
-from date import format_date
 
 import initialize  # noqa: unused-import
+import traceback
 from ajax import ajax, workaround_qt_bug
 from book_list.globals import get_session_data, set_session_data
 from book_list.library_data import library_data
-from book_list.theme import get_color, css_for_variables
+from book_list.theme import css_for_variables, get_color
+from date import format_date
 from dom import get_widget_css, set_css
+from gettext import gettext as _, install
 from modals import create_modal_container
 from qt import from_python, to_python
 from read_book.db import new_book
 from read_book.footnotes import main as footnotes_main
-from read_book.globals import runtime, set_system_colors, ui_operations, default_color_schemes
+from read_book.globals import (
+    default_color_schemes, runtime, set_system_colors, ui_operations
+)
 from read_book.iframe import main as iframe_main
-from read_book.view import View
+from read_book.open_book import remove_recently_opened
 from read_book.prefs.head_foot import set_time_formatter
+from read_book.view import View
 from session import local_storage, session_defaults
 from utils import debounce, encode_query_with_path, parse_url_params
 from viewer.constants import FAKE_HOST, FAKE_PROTOCOL, READER_BACKGROUND_URL
@@ -209,6 +212,8 @@ def generic_action(which, data):
         view.set_notes_for_highlight(data.uuid, data.notes or '')
     if which is 'show-status-message':
         view.show_status_message(data.text)
+    if which is 'remove-recently-opened':
+        remove_recently_opened(data.path)
 
 
 @from_python