diff --git a/openlp/core/lib/db.py b/openlp/core/lib/db.py
index 6d13c1d9b..9c594b14e 100644
--- a/openlp/core/lib/db.py
+++ b/openlp/core/lib/db.py
@@ -23,12 +23,13 @@
 """
 The :mod:`db` module provides the core database functionality for OpenLP
 """
+import json
 import logging
 import os
 from copy import copy
 from urllib.parse import quote_plus as urlquote
 
-from sqlalchemy import Table, MetaData, Column, types, create_engine
+from sqlalchemy import Table, MetaData, Column, types, create_engine, UnicodeText
 from sqlalchemy.engine.url import make_url
 from sqlalchemy.exc import SQLAlchemyError, InvalidRequestError, DBAPIError, OperationalError, ProgrammingError
 from sqlalchemy.orm import scoped_session, sessionmaker, mapper
@@ -37,7 +38,8 @@ from sqlalchemy.pool import NullPool
 from alembic.migration import MigrationContext
 from alembic.operations import Operations
 
-from openlp.core.common import AppLocation, Settings, translate, delete_file
+from openlp.core.common import AppLocation, Settings, delete_file, translate
+from openlp.core.common.json import OpenLPJsonDecoder, OpenLPJsonEncoder
 from openlp.core.lib.ui import critical_error_message_box
 
 log = logging.getLogger(__name__)
@@ -133,9 +135,10 @@ def get_db_path(plugin_name, db_file_name=None):
     if db_file_name is None:
         return 'sqlite:///{path}/{plugin}.sqlite'.format(path=AppLocation.get_section_data_path(plugin_name),
                                                          plugin=plugin_name)
+    elif os.path.isabs(db_file_name):
+        return 'sqlite:///{db_file_name}'.format(db_file_name=db_file_name)
     else:
-        return 'sqlite:///{path}/{name}'.format(path=AppLocation.get_section_data_path(plugin_name),
-                                                name=db_file_name)
+        return 'sqlite:///{path}/{name}'.format(path=AppLocation.get_section_data_path(plugin_name), name=db_file_name)
 
 
 def handle_db_error(plugin_name, db_file_name):
@@ -200,6 +203,54 @@ class BaseModel(object):
         return instance
 
 
+class PathType(types.TypeDecorator):
+    """
+    Create a PathType for storing Path objects with SQLAlchemy. Behind the scenes we convert the Path object to a JSON
+    representation and store it as a Unicode type
+    """
+    impl = types.UnicodeText
+
+    def coerce_compared_value(self, op, value):
+        """
+        Some times it make sense to compare a PathType with a string. In the case a string is used coerce the the
+        PathType to a UnicodeText type.
+        
+        :param op: The operation being carried out. Not used, as we only care about the type that is being used with the 
+                   operation.
+        :param openlp.core.common.path.Path | str value: The value being used for the comparison. Most likely a Path Object or str.
+        :return: The coerced value stored in the db
+        :rtype: PathType or UnicodeText
+        """
+        if isinstance(value, str):
+            return UnicodeText()
+        else:
+            return self
+
+    def process_bind_param(self, value, dialect):
+        """
+        Convert the Path object to a JSON representation
+
+        :param openlp.core.common.path.Path value: The value to convert
+        :param dialect: Not used
+        :return: The Path object as a JSON string
+        :rtype: str
+        """
+        data_path = AppLocation.get_data_path()
+        return json.dumps(value, cls=OpenLPJsonEncoder, base_path=data_path)
+
+    def process_result_value(self, value, dialect):
+        """
+        Convert the JSON representation back
+
+        :param types.UnicodeText value: The value to convert
+        :param dialect: Not used
+        :return: The JSON object converted Python object (in this case it should be a Path object)
+        :rtype: openlp.core.common.path.Path
+        """
+        data_path = AppLocation.get_data_path()
+        return json.loads(value, cls=OpenLPJsonDecoder, base_path=data_path)
+
+
 def upgrade_db(url, upgrade):
     """
     Upgrade a database.
@@ -208,7 +259,7 @@ def upgrade_db(url, upgrade):
     :param upgrade: The python module that contains the upgrade instructions.
     """
     if not database_exists(url):
-        log.warn("Database {db} doesn't exist - skipping upgrade checks".format(db=url))
+        log.warning("Database {db} doesn't exist - skipping upgrade checks".format(db=url))
         return (0, 0)
 
     log.debug('Checking upgrades for DB {db}'.format(db=url))
@@ -273,10 +324,11 @@ def delete_database(plugin_name, db_file_name=None):
     :param plugin_name: The name of the plugin to remove the database for
     :param db_file_name: The database file name. Defaults to None resulting in the plugin_name being used.
     """
+    db_file_path = AppLocation.get_section_data_path(plugin_name)
     if db_file_name:
-        db_file_path = AppLocation.get_section_data_path(plugin_name) / db_file_name
+        db_file_path = db_file_path / db_file_name
     else:
-        db_file_path = AppLocation.get_section_data_path(plugin_name) / plugin_name
+        db_file_path = db_file_path / plugin_name
     return delete_file(db_file_path)
 
 
@@ -284,30 +336,30 @@ class Manager(object):
     """
     Provide generic object persistence management
     """
-    def __init__(self, plugin_name, init_schema, db_file_name=None, upgrade_mod=None, session=None):
+    def __init__(self, plugin_name, init_schema, db_file_path=None, upgrade_mod=None, session=None):
         """
         Runs the initialisation process that includes creating the connection to the database and the tables if they do
         not exist.
 
         :param plugin_name:  The name to setup paths and settings section names
         :param init_schema: The init_schema function for this database
-        :param db_file_name: The upgrade_schema function for this database
-        :param upgrade_mod: The file name to use for this database. Defaults to None resulting in the plugin_name
+        :param openlp.core.common.path.Path db_file_path: The file name to use for this database. Defaults to None resulting in the plugin_name
         being used.
+        :param upgrade_mod: The upgrade_schema function for this database
         """
         self.is_dirty = False
         self.session = None
         self.db_url = None
-        if db_file_name:
+        if db_file_path:
             log.debug('Manager: Creating new DB url')
-            self.db_url = init_url(plugin_name, db_file_name)
+            self.db_url = init_url(plugin_name, str(db_file_path))
         else:
             self.db_url = init_url(plugin_name)
         if upgrade_mod:
             try:
                 db_ver, up_ver = upgrade_db(self.db_url, upgrade_mod)
             except (SQLAlchemyError, DBAPIError):
-                handle_db_error(plugin_name, db_file_name)
+                handle_db_error(plugin_name, str(db_file_path))
                 return
             if db_ver > up_ver:
                 critical_error_message_box(
@@ -322,7 +374,7 @@ class Manager(object):
             try:
                 self.session = init_schema(self.db_url)
             except (SQLAlchemyError, DBAPIError):
-                handle_db_error(plugin_name, db_file_name)
+                handle_db_error(plugin_name, str(db_file_path))
         else:
             self.session = session
 
diff --git a/openlp/core/ui/servicemanager.py b/openlp/core/ui/servicemanager.py
index b393ad736..b5b77d265 100644
--- a/openlp/core/ui/servicemanager.py
+++ b/openlp/core/ui/servicemanager.py
@@ -376,7 +376,7 @@ class ServiceManager(OpenLPMixin, RegistryMixin, QtWidgets.QWidget, Ui_ServiceMa
         self._file_name = path_to_str(file_path)
         self.main_window.set_service_modified(self.is_modified(), self.short_file_name())
         Settings().setValue('servicemanager/last file', file_path)
-        if file_path and file_path.suffix() == '.oszl':
+        if file_path and file_path.suffix == '.oszl':
             self._save_lite = True
         else:
             self._save_lite = False
@@ -699,13 +699,15 @@ class ServiceManager(OpenLPMixin, RegistryMixin, QtWidgets.QWidget, Ui_ServiceMa
             default_file_name = format_time(default_pattern, local_time)
         else:
             default_file_name = ''
+        default_file_path = Path(default_file_name)
         directory_path = Settings().value(self.main_window.service_manager_settings_section + '/last directory')
-        file_path = directory_path / default_file_name
+        if directory_path:
+            default_file_path = directory_path / default_file_path
         # SaveAs from osz to oszl is not valid as the files will be deleted on exit which is not sensible or usable in
         # the long term.
         if self._file_name.endswith('oszl') or self.service_has_all_original_files:
             file_path, filter_used = FileDialog.getSaveFileName(
-                self.main_window, UiStrings().SaveService, file_path,
+                self.main_window, UiStrings().SaveService, default_file_path,
                 translate('OpenLP.ServiceManager',
                           'OpenLP Service Files (*.osz);; OpenLP Service Files - lite (*.oszl)'))
         else:
diff --git a/openlp/plugins/images/imageplugin.py b/openlp/plugins/images/imageplugin.py
index a4310f170..36051a505 100644
--- a/openlp/plugins/images/imageplugin.py
+++ b/openlp/plugins/images/imageplugin.py
@@ -29,7 +29,7 @@ from openlp.core.common import Settings, translate
 from openlp.core.lib import Plugin, StringContent, ImageSource, build_icon
 from openlp.core.lib.db import Manager
 from openlp.plugins.images.endpoint import api_images_endpoint, images_endpoint
-from openlp.plugins.images.lib import ImageMediaItem, ImageTab
+from openlp.plugins.images.lib import ImageMediaItem, ImageTab, upgrade
 from openlp.plugins.images.lib.db import init_schema
 
 log = logging.getLogger(__name__)
@@ -50,7 +50,7 @@ class ImagePlugin(Plugin):
 
     def __init__(self):
         super(ImagePlugin, self).__init__('images', __default_settings__, ImageMediaItem, ImageTab)
-        self.manager = Manager('images', init_schema)
+        self.manager = Manager('images', init_schema, upgrade_mod=upgrade)
         self.weight = -7
         self.icon_path = ':/plugins/plugin_images.png'
         self.icon = build_icon(self.icon_path)
diff --git a/openlp/plugins/images/lib/db.py b/openlp/plugins/images/lib/db.py
index feb1174a8..be7c299b3 100644
--- a/openlp/plugins/images/lib/db.py
+++ b/openlp/plugins/images/lib/db.py
@@ -22,11 +22,10 @@
 """
 The :mod:`db` module provides the database and schema that is the backend for the Images plugin.
 """
-
 from sqlalchemy import Column, ForeignKey, Table, types
 from sqlalchemy.orm import mapper
 
-from openlp.core.lib.db import BaseModel, init_db
+from openlp.core.lib.db import BaseModel, PathType, init_db
 
 
 class ImageGroups(BaseModel):
@@ -65,7 +64,7 @@ def init_schema(url):
 
             * id
             * group_id
-            * filename
+            * file_path
     """
     session, metadata = init_db(url)
 
@@ -80,7 +79,7 @@ def init_schema(url):
     image_filenames_table = Table('image_filenames', metadata,
                                   Column('id', types.Integer(), primary_key=True),
                                   Column('group_id', types.Integer(), ForeignKey('image_groups.id'), default=None),
-                                  Column('filename', types.Unicode(255), nullable=False)
+                                  Column('file_path', PathType(), nullable=False)
                                   )
 
     mapper(ImageGroups, image_groups_table)
diff --git a/openlp/plugins/images/lib/imagetab.py b/openlp/plugins/images/lib/imagetab.py
index bacf03ce6..565ef6543 100644
--- a/openlp/plugins/images/lib/imagetab.py
+++ b/openlp/plugins/images/lib/imagetab.py
@@ -31,9 +31,6 @@ class ImageTab(SettingsTab):
     """
     ImageTab is the images settings tab in the settings dialog.
     """
-    def __init__(self, parent, name, visible_title, icon_path):
-        super(ImageTab, self).__init__(parent, name, visible_title, icon_path)
-
     def setupUi(self):
         self.setObjectName('ImagesTab')
         super(ImageTab, self).setupUi()
diff --git a/openlp/plugins/images/lib/mediaitem.py b/openlp/plugins/images/lib/mediaitem.py
index d1ea2003f..846c731fe 100644
--- a/openlp/plugins/images/lib/mediaitem.py
+++ b/openlp/plugins/images/lib/mediaitem.py
@@ -21,7 +21,6 @@
 ###############################################################################
 
 import logging
-import os
 
 from PyQt5 import QtCore, QtGui, QtWidgets
 
@@ -49,7 +48,7 @@ class ImageMediaItem(MediaManagerItem):
     log.info('Image Media Item loaded')
 
     def __init__(self, parent, plugin):
-        self.icon_path = 'images/image'
+        self.icon_resource = 'images/image'
         self.manager = None
         self.choose_group_form = None
         self.add_group_form = None
@@ -99,11 +98,11 @@ class ImageMediaItem(MediaManagerItem):
         self.list_view.setIconSize(QtCore.QSize(88, 50))
         self.list_view.setIndentation(self.list_view.default_indentation)
         self.list_view.allow_internal_dnd = True
-        self.service_path = os.path.join(str(AppLocation.get_section_data_path(self.settings_section)), 'thumbnails')
-        check_directory_exists(Path(self.service_path))
+        self.service_path = AppLocation.get_section_data_path(self.settings_section) / 'thumbnails'
+        check_directory_exists(self.service_path)
         # Load images from the database
         self.load_full_list(
-            self.manager.get_all_objects(ImageFilenames, order_by_ref=ImageFilenames.filename), initial_load=True)
+            self.manager.get_all_objects(ImageFilenames, order_by_ref=ImageFilenames.file_path), initial_load=True)
 
     def add_list_view_to_toolbar(self):
         """
@@ -211,8 +210,8 @@ class ImageMediaItem(MediaManagerItem):
         """
         images = self.manager.get_all_objects(ImageFilenames, ImageFilenames.group_id == image_group.id)
         for image in images:
-            delete_file(Path(self.service_path, os.path.split(image.filename)[1]))
-            delete_file(Path(self.generate_thumbnail_path(image)))
+            delete_file(self.service_path / image.file_path.name)
+            delete_file(self.generate_thumbnail_path(image))
             self.manager.delete_object(ImageFilenames, image.id)
         image_groups = self.manager.get_all_objects(ImageGroups, ImageGroups.parent_id == image_group.id)
         for group in image_groups:
@@ -234,8 +233,8 @@ class ImageMediaItem(MediaManagerItem):
                 if row_item:
                     item_data = row_item.data(0, QtCore.Qt.UserRole)
                     if isinstance(item_data, ImageFilenames):
-                        delete_file(Path(self.service_path, row_item.text(0)))
-                        delete_file(Path(self.generate_thumbnail_path(item_data)))
+                        delete_file(self.service_path / row_item.text(0))
+                        delete_file(self.generate_thumbnail_path(item_data))
                         if item_data.group_id == 0:
                             self.list_view.takeTopLevelItem(self.list_view.indexOfTopLevelItem(row_item))
                         else:
@@ -326,17 +325,19 @@ class ImageMediaItem(MediaManagerItem):
         """
         Generate a path to the thumbnail
 
-        :param image: An instance of ImageFileNames
-        :return: A path to the thumbnail of type str
+        :param openlp.plugins.images.lib.db.ImageFilenames image: The image to generate the thumbnail path for.
+        :return: A path to the thumbnail
+        :rtype: openlp.core.common.path.Path
         """
-        ext = os.path.splitext(image.filename)[1].lower()
-        return os.path.join(self.service_path, '{}{}'.format(str(image.id), ext))
+        ext = image.file_path.suffix.lower()
+        return self.service_path / '{name:d}{ext}'.format(name=image.id, ext=ext)
 
     def load_full_list(self, images, initial_load=False, open_group=None):
         """
         Replace the list of images and groups in the interface.
 
-        :param images: A List of Image Filenames objects that will be used to reload the mediamanager list.
+        :param list[openlp.plugins.images.lib.db.ImageFilenames] images: A List of Image Filenames objects that will be
+            used to reload the mediamanager list.
         :param initial_load: When set to False, the busy cursor and progressbar will be shown while loading images.
         :param open_group: ImageGroups object of the group that must be expanded after reloading the list in the
             interface.
@@ -352,34 +353,34 @@ class ImageMediaItem(MediaManagerItem):
             self.expand_group(open_group.id)
         # Sort the images by its filename considering language specific.
         # characters.
-        images.sort(key=lambda image_object: get_locale_key(os.path.split(str(image_object.filename))[1]))
-        for image_file in images:
-            log.debug('Loading image: {name}'.format(name=image_file.filename))
-            filename = os.path.split(image_file.filename)[1]
-            thumb = self.generate_thumbnail_path(image_file)
-            if not os.path.exists(image_file.filename):
+        images.sort(key=lambda image_object: get_locale_key(image_object.file_path.name))
+        for image in images:
+            log.debug('Loading image: {name}'.format(name=image.file_path))
+            file_name = image.file_path.name
+            thumbnail_path = self.generate_thumbnail_path(image)
+            if not image.file_path.exists():
                 icon = build_icon(':/general/general_delete.png')
             else:
-                if validate_thumb(Path(image_file.filename), Path(thumb)):
-                    icon = build_icon(thumb)
+                if validate_thumb(image.file_path, thumbnail_path):
+                    icon = build_icon(thumbnail_path)
                 else:
-                    icon = create_thumb(image_file.filename, thumb)
-            item_name = QtWidgets.QTreeWidgetItem([filename])
-            item_name.setText(0, filename)
+                    icon = create_thumb(image.file_path, thumbnail_path)
+            item_name = QtWidgets.QTreeWidgetItem([file_name])
+            item_name.setText(0, file_name)
             item_name.setIcon(0, icon)
-            item_name.setToolTip(0, image_file.filename)
-            item_name.setData(0, QtCore.Qt.UserRole, image_file)
-            if image_file.group_id == 0:
+            item_name.setToolTip(0, str(image.file_path))
+            item_name.setData(0, QtCore.Qt.UserRole, image)
+            if image.group_id == 0:
                 self.list_view.addTopLevelItem(item_name)
             else:
-                group_items[image_file.group_id].addChild(item_name)
+                group_items[image.group_id].addChild(item_name)
             if not initial_load:
                 self.main_window.increment_progress_bar()
         if not initial_load:
             self.main_window.finished_progress_bar()
         self.application.set_normal_cursor()
 
-    def validate_and_load(self, files, target_group=None):
+    def validate_and_load(self, file_paths, target_group=None):
         """
         Process a list for files either from the File Dialog or from Drag and Drop.
         This method is overloaded from MediaManagerItem.
@@ -388,15 +389,15 @@ class ImageMediaItem(MediaManagerItem):
         :param target_group: The QTreeWidgetItem of the group that will be the parent of the added files
         """
         self.application.set_normal_cursor()
-        self.load_list(files, target_group)
-        last_dir = os.path.split(files[0])[0]
-        Settings().setValue(self.settings_section + '/last directory', Path(last_dir))
+        self.load_list(file_paths, target_group)
+        last_dir = file_paths[0].parent
+        Settings().setValue(self.settings_section + '/last directory', last_dir)
 
-    def load_list(self, images, target_group=None, initial_load=False):
+    def load_list(self, image_paths, target_group=None, initial_load=False):
         """
         Add new images to the database. This method is called when adding images using the Add button or DnD.
 
-        :param images: A List of strings containing the filenames of the files to be loaded
+        :param list[openlp.core.common.Path] image_paths: A list of file paths to the images to be loaded
         :param target_group: The QTreeWidgetItem of the group that will be the parent of the added files
         :param initial_load: When set to False, the busy cursor and progressbar will be shown while loading images
         """
@@ -429,7 +430,7 @@ class ImageMediaItem(MediaManagerItem):
             else:
                 self.choose_group_form.existing_radio_button.setDisabled(False)
                 self.choose_group_form.group_combobox.setDisabled(False)
-            # Ask which group the images should be saved in
+            # Ask which group the image_paths should be saved in
             if self.choose_group_form.exec(selected_group=preselect_group):
                 if self.choose_group_form.nogroup_radio_button.isChecked():
                     # User chose 'No group'
@@ -461,33 +462,33 @@ class ImageMediaItem(MediaManagerItem):
             return
         # Initialize busy cursor and progress bar
         self.application.set_busy_cursor()
-        self.main_window.display_progress_bar(len(images))
-        # Save the new images in the database
-        self.save_new_images_list(images, group_id=parent_group.id, reload_list=False)
-        self.load_full_list(self.manager.get_all_objects(ImageFilenames, order_by_ref=ImageFilenames.filename),
+        self.main_window.display_progress_bar(len(image_paths))
+        # Save the new image_paths in the database
+        self.save_new_images_list(image_paths, group_id=parent_group.id, reload_list=False)
+        self.load_full_list(self.manager.get_all_objects(ImageFilenames, order_by_ref=ImageFilenames.file_path),
                             initial_load=initial_load, open_group=parent_group)
         self.application.set_normal_cursor()
 
-    def save_new_images_list(self, images_list, group_id=0, reload_list=True):
+    def save_new_images_list(self, image_paths, group_id=0, reload_list=True):
         """
         Convert a list of image filenames to ImageFilenames objects and save them in the database.
 
-        :param images_list: A List of strings containing image filenames
+        :param list[Path] image_paths: A List of file paths to image
         :param group_id: The ID of the group to save the images in
         :param reload_list: This boolean is set to True when the list in the interface should be reloaded after saving
             the new images
         """
-        for filename in images_list:
-            if not isinstance(filename, str):
+        for image_path in image_paths:
+            if not isinstance(image_path, Path):
                 continue
-            log.debug('Adding new image: {name}'.format(name=filename))
+            log.debug('Adding new image: {name}'.format(name=image_path))
             image_file = ImageFilenames()
             image_file.group_id = group_id
-            image_file.filename = str(filename)
+            image_file.file_path = image_path
             self.manager.save_object(image_file)
             self.main_window.increment_progress_bar()
-        if reload_list and images_list:
-            self.load_full_list(self.manager.get_all_objects(ImageFilenames, order_by_ref=ImageFilenames.filename))
+        if reload_list and image_paths:
+            self.load_full_list(self.manager.get_all_objects(ImageFilenames, order_by_ref=ImageFilenames.file_path))
 
     def dnd_move_internal(self, target):
         """
@@ -581,8 +582,8 @@ class ImageMediaItem(MediaManagerItem):
             return False
         # Find missing files
         for image in images:
-            if not os.path.exists(image.filename):
-                missing_items_file_names.append(image.filename)
+            if not image.file_path.exists():
+                missing_items_file_names.append(str(image.file_path))
         # We cannot continue, as all images do not exist.
         if not images:
             if not remote:
@@ -601,9 +602,9 @@ class ImageMediaItem(MediaManagerItem):
             return False
         # Continue with the existing images.
         for image in images:
-            name = os.path.split(image.filename)[1]
-            thumbnail = self.generate_thumbnail_path(image)
-            service_item.add_from_image(image.filename, name, background, thumbnail)
+            name = image.file_path.name
+            thumbnail_path = self.generate_thumbnail_path(image)
+            service_item.add_from_image(str(image.file_path), name, background, str(thumbnail_path))
         return True
 
     def check_group_exists(self, new_group):
@@ -640,7 +641,7 @@ class ImageMediaItem(MediaManagerItem):
             if not self.check_group_exists(new_group):
                 if self.manager.save_object(new_group):
                     self.load_full_list(self.manager.get_all_objects(
-                        ImageFilenames, order_by_ref=ImageFilenames.filename))
+                        ImageFilenames, order_by_ref=ImageFilenames.file_path))
                     self.expand_group(new_group.id)
                     self.fill_groups_combobox(self.choose_group_form.group_combobox)
                     self.fill_groups_combobox(self.add_group_form.parent_group_combobox)
@@ -675,9 +676,9 @@ class ImageMediaItem(MediaManagerItem):
             if not isinstance(bitem.data(0, QtCore.Qt.UserRole), ImageFilenames):
                 # Only continue when an image is selected.
                 return
-            filename = bitem.data(0, QtCore.Qt.UserRole).filename
-            if os.path.exists(filename):
-                if self.live_controller.display.direct_image(filename, background):
+            file_path = bitem.data(0, QtCore.Qt.UserRole).file_path
+            if file_path.exists():
+                if self.live_controller.display.direct_image(str(file_path), background):
                     self.reset_action.setVisible(True)
                 else:
                     critical_error_message_box(
@@ -687,22 +688,22 @@ class ImageMediaItem(MediaManagerItem):
                 critical_error_message_box(
                     UiStrings().LiveBGError,
                     translate('ImagePlugin.MediaItem', 'There was a problem replacing your background, '
-                              'the image file "{name}" no longer exists.').format(name=filename))
+                              'the image file "{name}" no longer exists.').format(name=file_path))
 
     def search(self, string, show_error=True):
         """
         Perform a search on the image file names.
 
-        :param string: The glob to search for
-        :param show_error: Unused.
+        :param str string: The glob to search for
+        :param bool show_error: Unused.
         """
         files = self.manager.get_all_objects(
-            ImageFilenames, filter_clause=ImageFilenames.filename.contains(string),
-            order_by_ref=ImageFilenames.filename)
+            ImageFilenames, filter_clause=ImageFilenames.file_path.contains(string),
+            order_by_ref=ImageFilenames.file_path)
         results = []
         for file_object in files:
-            filename = os.path.split(str(file_object.filename))[1]
-            results.append([file_object.filename, filename])
+            file_name = file_object.file_path.name
+            results.append([str(file_object.file_path), file_name])
         return results
 
     def create_item_from_id(self, item_id):
@@ -711,8 +712,9 @@ class ImageMediaItem(MediaManagerItem):
 
         :param item_id: Id to make live
         """
+        item_id = Path(item_id)
         item = QtWidgets.QTreeWidgetItem()
-        item_data = self.manager.get_object_filtered(ImageFilenames, ImageFilenames.filename == item_id)
-        item.setText(0, os.path.basename(item_data.filename))
+        item_data = self.manager.get_object_filtered(ImageFilenames, ImageFilenames.file_path == item_id)
+        item.setText(0, item_data.file_path.name)
         item.setData(0, QtCore.Qt.UserRole, item_data)
         return item
diff --git a/openlp/plugins/images/lib/upgrade.py b/openlp/plugins/images/lib/upgrade.py
new file mode 100644
index 000000000..63690d404
--- /dev/null
+++ b/openlp/plugins/images/lib/upgrade.py
@@ -0,0 +1,70 @@
+# -*- coding: utf-8 -*-
+# vim: autoindent shiftwidth=4 expandtab textwidth=120 tabstop=4 softtabstop=4
+
+###############################################################################
+# OpenLP - Open Source Lyrics Projection                                      #
+# --------------------------------------------------------------------------- #
+# Copyright (c) 2008-2017 OpenLP Developers                                   #
+# --------------------------------------------------------------------------- #
+# This program is free software; you can redistribute it and/or modify it     #
+# under the terms of the GNU General Public License as published by the Free  #
+# Software Foundation; version 2 of the License.                              #
+#                                                                             #
+# This program is distributed in the hope that it will be useful, but WITHOUT #
+# ANY WARRANTY; without even the implied warranty of MERCHANTABILITY or       #
+# FITNESS FOR A PARTICULAR PURPOSE. See the GNU General Public License for    #
+# more details.                                                               #
+#                                                                             #
+# You should have received a copy of the GNU General Public License along     #
+# with this program; if not, write to the Free Software Foundation, Inc., 59  #
+# Temple Place, Suite 330, Boston, MA 02111-1307 USA                          #
+###############################################################################
+"""
+The :mod:`upgrade` module provides the migration path for the OLP Paths database
+"""
+import json
+import logging
+
+from sqlalchemy import Column, Table
+
+from openlp.core.common import AppLocation
+from openlp.core.common.db import drop_columns
+from openlp.core.common.json import OpenLPJsonEncoder
+from openlp.core.common.path import Path
+from openlp.core.lib.db import PathType, get_upgrade_op
+
+log = logging.getLogger(__name__)
+__version__ = 2
+
+
+def upgrade_1(session, metadata):
+    """
+    Version 1 upgrade - old db might/might not be versioned.
+    """
+    log.debug('Skipping upgrade_1 of files DB - not used')
+
+
+def upgrade_2(session, metadata):
+    """
+    Version 2 upgrade - Move file path from old db to JSON encoded path to new db. Added during 2.5 dev
+    """
+    # TODO: Update tests
+    log.debug('Starting upgrade_2 for file_path to JSON')
+    old_table = Table('image_filenames', metadata, autoload=True)
+    if 'file_path' not in [col.name for col in old_table.c.values()]:
+        op = get_upgrade_op(session)
+        op.add_column('image_filenames', Column('file_path', PathType()))
+        conn = op.get_bind()
+        results = conn.execute('SELECT * FROM image_filenames')
+        data_path = AppLocation.get_data_path()
+        for row in results.fetchall():
+            file_path_json = json.dumps(Path(row.filename), cls=OpenLPJsonEncoder, base_path=data_path)
+            sql = 'UPDATE image_filenames SET file_path = \'{file_path_json}\' WHERE id = {id}'.format(
+                file_path_json=file_path_json, id=row.id)
+            conn.execute(sql)
+        # Drop old columns
+        if metadata.bind.url.get_dialect().name == 'sqlite':
+            drop_columns(op, 'image_filenames', ['filename', ])
+        else:
+            op.drop_constraint('image_filenames', 'foreignkey')
+            op.drop_column('image_filenames', 'filenames')
diff --git a/tests/functional/openlp_plugins/images/test_lib.py b/tests/functional/openlp_plugins/images/test_lib.py
index 821a64bb0..650179e07 100644
--- a/tests/functional/openlp_plugins/images/test_lib.py
+++ b/tests/functional/openlp_plugins/images/test_lib.py
@@ -58,7 +58,7 @@ class TestImageMediaItem(TestCase):
         Test that the validate_and_load_test() method when called without a group
         """
         # GIVEN: A list of files
-        file_list = ['/path1/image1.jpg', '/path2/image2.jpg']
+        file_list = [Path('path1', 'image1.jpg'), Path('path2', 'image2.jpg')]
 
         # WHEN: Calling validate_and_load with the list of files
         self.media_item.validate_and_load(file_list)
@@ -66,7 +66,7 @@ class TestImageMediaItem(TestCase):
         # THEN: load_list should have been called with the file list and None,
         #       the directory should have been saved to the settings
         mocked_load_list.assert_called_once_with(file_list, None)
-        mocked_settings().setValue.assert_called_once_with(ANY, Path('/', 'path1'))
+        mocked_settings().setValue.assert_called_once_with(ANY, Path('path1'))
 
     @patch('openlp.plugins.images.lib.mediaitem.ImageMediaItem.load_list')
     @patch('openlp.plugins.images.lib.mediaitem.Settings')
@@ -75,7 +75,7 @@ class TestImageMediaItem(TestCase):
         Test that the validate_and_load_test() method when called with a group
         """
         # GIVEN: A list of files
-        file_list = ['/path1/image1.jpg', '/path2/image2.jpg']
+        file_list = [Path('path1', 'image1.jpg'), Path('path2', 'image2.jpg')]
 
         # WHEN: Calling validate_and_load with the list of files and a group
         self.media_item.validate_and_load(file_list, 'group')
@@ -83,7 +83,7 @@ class TestImageMediaItem(TestCase):
         # THEN: load_list should have been called with the file list and the group name,
         #       the directory should have been saved to the settings
         mocked_load_list.assert_called_once_with(file_list, 'group')
-        mocked_settings().setValue.assert_called_once_with(ANY, Path('/', 'path1'))
+        mocked_settings().setValue.assert_called_once_with(ANY, Path('path1'))
 
     @patch('openlp.plugins.images.lib.mediaitem.ImageMediaItem.load_full_list')
     def test_save_new_images_list_empty_list(self, mocked_load_full_list):
@@ -107,8 +107,8 @@ class TestImageMediaItem(TestCase):
         Test that the save_new_images_list() calls load_full_list() when reload_list is set to True
         """
         # GIVEN: A list with 1 image and a mocked out manager
-        image_list = ['test_image.jpg']
-        ImageFilenames.filename = ''
+        image_list = [Path('test_image.jpg')]
+        ImageFilenames.file_path = None
         self.media_item.manager = MagicMock()
 
         # WHEN: We run save_new_images_list with reload_list=True
@@ -118,7 +118,7 @@ class TestImageMediaItem(TestCase):
         self.assertEquals(mocked_load_full_list.call_count, 1, 'load_full_list() should have been called')
 
         # CLEANUP: Remove added attribute from ImageFilenames
-        delattr(ImageFilenames, 'filename')
+        delattr(ImageFilenames, 'file_path')
 
     @patch('openlp.plugins.images.lib.mediaitem.ImageMediaItem.load_full_list')
     def test_save_new_images_list_single_image_without_reload(self, mocked_load_full_list):
@@ -126,7 +126,7 @@ class TestImageMediaItem(TestCase):
         Test that the save_new_images_list() doesn't call load_full_list() when reload_list is set to False
         """
         # GIVEN: A list with 1 image and a mocked out manager
-        image_list = ['test_image.jpg']
+        image_list = [Path('test_image.jpg')]
         self.media_item.manager = MagicMock()
 
         # WHEN: We run save_new_images_list with reload_list=False
@@ -141,7 +141,7 @@ class TestImageMediaItem(TestCase):
         Test that the save_new_images_list() saves all images in the list
         """
         # GIVEN: A list with 3 images
-        image_list = ['test_image_1.jpg', 'test_image_2.jpg', 'test_image_3.jpg']
+        image_list = [Path('test_image_1.jpg'), Path('test_image_2.jpg'), Path('test_image_3.jpg')]
         self.media_item.manager = MagicMock()
 
         # WHEN: We run save_new_images_list with the list of 3 images
@@ -157,7 +157,7 @@ class TestImageMediaItem(TestCase):
         Test that the save_new_images_list() ignores everything in the provided list except strings
         """
         # GIVEN: A list with images and objects
-        image_list = ['test_image_1.jpg', None, True, ImageFilenames(), 'test_image_2.jpg']
+        image_list = [Path('test_image_1.jpg'), None, True, ImageFilenames(), Path('test_image_2.jpg')]
         self.media_item.manager = MagicMock()
 
         # WHEN: We run save_new_images_list with the list of images and objects
@@ -191,7 +191,7 @@ class TestImageMediaItem(TestCase):
         ImageGroups.parent_id = 1
         self.media_item.manager = MagicMock()
         self.media_item.manager.get_all_objects.side_effect = self._recursively_delete_group_side_effect
-        self.media_item.service_path = ''
+        self.media_item.service_path = Path()
         test_group = ImageGroups()
         test_group.id = 1
 
@@ -215,13 +215,13 @@ class TestImageMediaItem(TestCase):
             # Create some fake objects that should be removed
             returned_object1 = ImageFilenames()
             returned_object1.id = 1
-            returned_object1.filename = '/tmp/test_file_1.jpg'
+            returned_object1.file_path = Path('/', 'tmp', 'test_file_1.jpg')
             returned_object2 = ImageFilenames()
             returned_object2.id = 2
-            returned_object2.filename = '/tmp/test_file_2.jpg'
+            returned_object2.file_path = Path('/', 'tmp', 'test_file_2.jpg')
             returned_object3 = ImageFilenames()
             returned_object3.id = 3
-            returned_object3.filename = '/tmp/test_file_3.jpg'
+            returned_object3.file_path = Path('/', 'tmp', 'test_file_3.jpg')
             return [returned_object1, returned_object2, returned_object3]
         if args[1] == ImageGroups and args[2]:
             # Change the parent_id that is matched so we don't get into an endless loop
@@ -243,9 +243,9 @@ class TestImageMediaItem(TestCase):
         test_image = ImageFilenames()
         test_image.id = 1
         test_image.group_id = 1
-        test_image.filename = 'imagefile.png'
+        test_image.file_path = Path('imagefile.png')
         self.media_item.manager = MagicMock()
-        self.media_item.service_path = ''
+        self.media_item.service_path = Path()
         self.media_item.list_view = MagicMock()
         mocked_row_item = MagicMock()
         mocked_row_item.data.return_value = test_image
@@ -265,13 +265,13 @@ class TestImageMediaItem(TestCase):
         # GIVEN: An ImageFilenames that already exists in the database
         image_file = ImageFilenames()
         image_file.id = 1
-        image_file.filename = '/tmp/test_file_1.jpg'
+        image_file.file_path = Path('/', 'tmp', 'test_file_1.jpg')
         self.media_item.manager = MagicMock()
         self.media_item.manager.get_object_filtered.return_value = image_file
-        ImageFilenames.filename = ''
+        ImageFilenames.file_path = None
 
         # WHEN: create_item_from_id() is called
-        item = self.media_item.create_item_from_id(1)
+        item = self.media_item.create_item_from_id('1')
 
         # THEN: A QTreeWidgetItem should be created with the above model object as it's data
         self.assertIsInstance(item, QtWidgets.QTreeWidgetItem)
@@ -279,4 +279,4 @@ class TestImageMediaItem(TestCase):
         item_data = item.data(0, QtCore.Qt.UserRole)
         self.assertIsInstance(item_data, ImageFilenames)
         self.assertEqual(1, item_data.id)
-        self.assertEqual('/tmp/test_file_1.jpg', item_data.filename)
+        self.assertEqual(Path('/', 'tmp', 'test_file_1.jpg'), item_data.file_path)
diff --git a/tests/functional/openlp_plugins/images/test_upgrade.py b/tests/functional/openlp_plugins/images/test_upgrade.py
new file mode 100644
index 000000000..e9f74b775
--- /dev/null
+++ b/tests/functional/openlp_plugins/images/test_upgrade.py
@@ -0,0 +1,83 @@
+# -*- coding: utf-8 -*-
+# vim: autoindent shiftwidth=4 expandtab textwidth=120 tabstop=4 softtabstop=4
+
+###############################################################################
+# OpenLP - Open Source Lyrics Projection                                      #
+# --------------------------------------------------------------------------- #
+# Copyright (c) 2008-2017 OpenLP Developers                                   #
+# --------------------------------------------------------------------------- #
+# This program is free software; you can redistribute it and/or modify it     #
+# under the terms of the GNU General Public License as published by the Free  #
+# Software Foundation; version 2 of the License.                              #
+#                                                                             #
+# This program is distributed in the hope that it will be useful, but WITHOUT #
+# ANY WARRANTY; without even the implied warranty of MERCHANTABILITY or       #
+# FITNESS FOR A PARTICULAR PURPOSE. See the GNU General Public License for    #
+# more details.                                                               #
+#                                                                             #
+# You should have received a copy of the GNU General Public License along     #
+# with this program; if not, write to the Free Software Foundation, Inc., 59  #
+# Temple Place, Suite 330, Boston, MA 02111-1307 USA                          #
+###############################################################################
+"""
+This module contains tests for the lib submodule of the Images plugin.
+"""
+import os
+import shutil
+from tempfile import mkdtemp
+from unittest import TestCase
+from unittest.mock import patch
+
+from openlp.core.common import AppLocation, Settings
+from openlp.core.common.path import Path
+from openlp.core.lib.db import Manager
+from openlp.plugins.images.lib import upgrade
+from openlp.plugins.images.lib.db import ImageFilenames, init_schema
+
+from tests.helpers.testmixin import TestMixin
+from tests.utils.constants import TEST_RESOURCES_PATH
+
+__default_settings__ = {
+    'images/db type': 'sqlite',
+    'images/background color': '#000000',
+}
+
+
+class TestImageDBUpgrade(TestCase, TestMixin):
+    """
+    Test that the image database is upgraded correctly
+    """
+    def setUp(self):
+        self.build_settings()
+        Settings().extend_default_settings(__default_settings__)
+        self.tmp_folder = mkdtemp()
+
+    def tearDown(self):
+        """
+        Delete all the C++ objects at the end so that we don't have a segfault
+        """
+        self.destroy_settings()
+        # Ignore errors since windows can have problems with locked files
+        shutil.rmtree(self.tmp_folder, ignore_errors=True)
+
+    def test_image_filenames_table(self):
+        """
+        Test that the ImageFilenames table is correctly upgraded to the latest version 
+        """
+        # GIVEN: An unversioned image database
+        temp_db_name = os.path.join(self.tmp_folder, 'image-v0.sqlite')
+        shutil.copyfile(os.path.join(TEST_RESOURCES_PATH, 'images', 'image-v0.sqlite'), temp_db_name)
+
+        with patch.object(AppLocation, 'get_data_path', return_value=Path('/', 'test', 'dir')):
+            # WHEN: Initalising the database manager
+            manager = Manager('images', init_schema, db_file_path=temp_db_name, upgrade_mod=upgrade)
+
+            # THEN: The database should have been upgraded and image_filenames.file_path should return Path objects
+            upgraded_results = manager.get_all_objects(ImageFilenames)
+
+            expected_result_data = {1: Path('/', 'test', 'image1.jpg'),
+                                    2: Path('/', 'test', 'dir', 'image2.jpg'),
+                                    3: Path('/', 'test', 'dir', 'subdir', 'image3.jpg')}
+
+            for result in upgraded_results:
+                self.assertEqual(expected_result_data[result.id], result.file_path)
diff --git a/tests/resources/images/image-v0.sqlite b/tests/resources/images/image-v0.sqlite
new file mode 100644
index 000000000..92e199bfd
Binary files /dev/null and b/tests/resources/images/image-v0.sqlite differ