diff --git a/src/calibre/gui2/open_with.py b/src/calibre/gui2/open_with.py
index 4791737550..4b290df57c 100644
--- a/src/calibre/gui2/open_with.py
+++ b/src/calibre/gui2/open_with.py
@@ -73,13 +73,23 @@ if iswindows:
         return sort_key(entry.get('name') or '')
 
     def finalize_entry(entry):
-        data = load_icon_resource(entry.pop('icon_resource', None), as_data=True)
+        try:
+            data = load_icon_resource(entry.pop('icon_resource', None), as_data=True)
+        except Exception:
+            data = None
+            import traceback
+            traceback.print_exc()
         if data:
             entry['icon_data'] = data
         return entry
 
     def entry_to_item(entry, parent):
-        icon = load_icon_resource(entry.get('icon_resource'))
+        try:
+            icon = load_icon_resource(entry.get('icon_resource'))
+        except Exception:
+            icon = None
+            import traceback
+            traceback.print_exc()
         if not icon:
             icon = entry_to_icon_text(entry)[0]
         ans = QListWidgetItem(QIcon(icon), entry.get('name') or _('Unknown'), parent)
diff --git a/src/calibre/utils/open_with/windows.py b/src/calibre/utils/open_with/windows.py
index 532483c559..3435945976 100644
--- a/src/calibre/utils/open_with/windows.py
+++ b/src/calibre/utils/open_with/windows.py
@@ -11,9 +11,12 @@ from collections import namedtuple
 from future_builtins import map
 
 from PyQt5.Qt import QtWin, Qt, QIcon, QByteArray, QBuffer, QPixmap
-import win32con, win32api, win32gui
+import win32con, win32api, win32gui, pywintypes, winerror
 
+from calibre import prints
 from calibre.gui2 import must_use_qt
+from calibre.utils.winreg.default_programs import split_commandline
+
 ICON_SIZE = 64
 
 def hicon_to_pixmap(hicon):
@@ -33,7 +36,13 @@ def copy_to_size(pixmap, size=ICON_SIZE):
 
 def simple_load_icon(module, index, as_data=False, size=ICON_SIZE):
     ' Use the win32 API ExtractIcon to load the icon. This restricts icon size to 32x32, but has less chance of failing '
-    large_icons, small_icons = win32gui.ExtractIconEx(module, index, 10)
+    try:
+        large_icons, small_icons = win32gui.ExtractIconEx(module, index, 10)
+    except pywintypes.error as err:
+        if err.winerror != winerror.ERROR_FILE_NOT_FOUND:
+            raise
+        prints('File %r does not exist, cannot load icon' % module)
+        return
     icons = large_icons + small_icons
     try:
         if icons:
@@ -104,6 +113,8 @@ def load_icon_resource(icon_resource, as_data=False, size=ICON_SIZE):
         return
     module, index = parts
     index = int(index)
+    if module.startswith('"') and module.endswith('"'):
+        module = split_commandline(module)[0]
     try:
         return load_icon(module, index, as_data=as_data, size=size)
     except Exception: