diff --git a/openlp/plugins/images/lib/mediaitem.py b/openlp/plugins/images/lib/mediaitem.py
index 59443100a..5a1b142e5 100644
--- a/openlp/plugins/images/lib/mediaitem.py
+++ b/openlp/plugins/images/lib/mediaitem.py
@@ -575,6 +575,7 @@ class ImageMediaItem(MediaManagerItem):
         service_item.theme = -1
         missing_items_file_names = []
         images = []
+        existing_images = []
         # Expand groups to images
         for bitem in items:
             if isinstance(bitem.data(0, QtCore.Qt.UserRole), ImageGroups) or bitem.data(0, QtCore.Qt.UserRole) is None:
@@ -590,8 +591,10 @@ class ImageMediaItem(MediaManagerItem):
         for image in images:
             if not image.file_path.exists():
                 missing_items_file_names.append(str(image.file_path))
+            else:
+                existing_images.append(image)
         # We cannot continue, as all images do not exist.
-        if not images:
+        if not existing_images:
             if not remote:
                 critical_error_message_box(
                     translate('ImagePlugin.MediaItem', 'Missing Image(s)'),
@@ -607,7 +610,7 @@ class ImageMediaItem(MediaManagerItem):
                 QtWidgets.QMessageBox.No:
             return False
         # Continue with the existing images.
-        for image in images:
+        for image in existing_images:
             name = image.file_path.name
             thumbnail_path = self.generate_thumbnail_path(image)
             service_item.add_from_image(image.file_path, name, thumbnail_path)
diff --git a/openlp/plugins/images/lib/upgrade.py b/openlp/plugins/images/lib/upgrade.py
index 89cd6e019..addd41f20 100644
--- a/openlp/plugins/images/lib/upgrade.py
+++ b/openlp/plugins/images/lib/upgrade.py
@@ -85,7 +85,12 @@ def upgrade_3(session, metadata):
         thumb_path = AppLocation.get_data_path() / 'images' / 'thumbnails'
         for row in results.fetchall():
             file_path = json.loads(row.file_path, cls=OpenLPJSONDecoder)
-            hash = sha256_file_hash(file_path)
+            if file_path.exists():
+                hash = sha256_file_hash(file_path)
+            else:
+                log.warning('{image} does not exists, so no sha256 hash added.'.format(image=str(file_path)))
+                # set a fake "hash" to allow for the upgrade to go through. The image will be marked as invalid
+                hash = 'NONE'
             sql = 'UPDATE image_filenames SET file_hash = \'{hash}\' WHERE id = {id}'.format(hash=hash, id=row.id)
             conn.execute(sql)
             # rename thumbnail to use file hash
diff --git a/openlp/plugins/presentations/lib/mediaitem.py b/openlp/plugins/presentations/lib/mediaitem.py
index b3499db7f..133dc23d7 100644
--- a/openlp/plugins/presentations/lib/mediaitem.py
+++ b/openlp/plugins/presentations/lib/mediaitem.py
@@ -234,7 +234,10 @@ class PresentationMediaItem(MediaManagerItem):
             self.application.set_busy_cursor()
             self.main_window.display_progress_bar(len(row_list))
             for item in items:
-                self.clean_up_thumbnails(item.data(QtCore.Qt.UserRole))
+                file_path = item.data(QtCore.Qt.UserRole)
+                # cleaning thumbnails depends on being able to calculate sha256 hash of the actual file
+                if file_path.exists():
+                    self.clean_up_thumbnails(file_path)
                 self.main_window.increment_progress_bar()
             self.main_window.finished_progress_bar()
             for row in row_list:
diff --git a/tests/functional/openlp_core/lib/test_serviceitem.py b/tests/functional/openlp_core/lib/test_serviceitem.py
index 90e2761e2..31253df10 100644
--- a/tests/functional/openlp_core/lib/test_serviceitem.py
+++ b/tests/functional/openlp_core/lib/test_serviceitem.py
@@ -26,7 +26,7 @@ import pytest
 from pathlib import Path
 from unittest.mock import Mock, MagicMock, patch
 
-from openlp.core.common import ThemeLevel
+from openlp.core.common import ThemeLevel, is_win
 from openlp.core.common.enum import ServiceItemType
 from openlp.core.common.registry import Registry
 from openlp.core.lib.formattingtags import FormattingTags
@@ -563,16 +563,21 @@ def test_to_dict_text_item(state_media, settings, service_item_env):
     service_item.add_icon = MagicMock()
     FormattingTags.load_tags()
     line = convert_file_service_item(TEST_PATH, 'serviceitem-song-linked-audio.osj')
-    service_item.set_from_service(line, Path('/test/'))
+    if is_win():
+        fake_path = Path('c:\\test\\')
+    else:
+        fake_path = Path('/test/')
+    service_item.set_from_service(line, fake_path)
 
     # WHEN: to_dict() is called
     result = service_item.to_dict()
 
     # THEN: The correct dictionary should be returned
+    expected_fake_path = str(fake_path / 'amazing_grace.mp3')
     expected_dict = {
 
         'audit': ['Amazing Grace', ['John Newton'], '', ''],
-        'backgroundAudio': ['/test/amazing_grace.mp3'],
+        'backgroundAudio': [expected_fake_path],
         'capabilities': [2, 1, 5, 8, 9, 13, 15],
         'footer': ['Amazing Grace', 'Written by: John Newton'],
         'fromPlugin': False,