diff --git a/openlp/core/__init__.py b/openlp/core/__init__.py
index ebb2d6c22..3a203c2c4 100644
--- a/openlp/core/__init__.py
+++ b/openlp/core/__init__.py
@@ -405,7 +405,7 @@ def main(args=None):
         # Set our data path
         log.info('Data path: {name}'.format(name=data_path))
         # Point to our data path
-        portable_settings.setValue('advanced/data path', str(data_path))
+        portable_settings.setValue('advanced/data path', data_path)
         portable_settings.setValue('advanced/is portable', True)
         portable_settings.sync()
     else:
@@ -422,8 +422,8 @@ def main(args=None):
     if application.is_data_path_missing():
         application.shared_memory.detach()
         sys.exit()
-    # Remove/convert obsolete settings.
-    Settings().remove_obsolete_settings()
+    # Upgrade settings.
+    Settings().upgrade_settings()
     # First time checks in settings
     if not Settings().value('core/has run wizard'):
         if not FirstTimeLanguageForm().exec():
diff --git a/openlp/core/api/endpoint/controller.py b/openlp/core/api/endpoint/controller.py
index 85e9623f9..c3f5fd89f 100644
--- a/openlp/core/api/endpoint/controller.py
+++ b/openlp/core/api/endpoint/controller.py
@@ -79,8 +79,7 @@ def controller_text(request):
                     item['title'] = str(frame['display_title'])
                 if current_item.is_capable(ItemCapabilities.HasNotes):
                     item['slide_notes'] = str(frame['notes'])
-                if current_item.is_capable(ItemCapabilities.HasThumbnails) and \
-                        Settings().value('api/thumbnails'):
+                if current_item.is_capable(ItemCapabilities.HasThumbnails) and Settings().value('api/thumbnails'):
                     # If the file is under our app directory tree send the portion after the match
                     data_path = str(AppLocation.get_data_path())
                     if frame['image'][0:len(data_path)] == data_path:
diff --git a/openlp/core/common/applocation.py b/openlp/core/common/applocation.py
index 29ca6fb3e..87ef7e6c1 100644
--- a/openlp/core/common/applocation.py
+++ b/openlp/core/common/applocation.py
@@ -86,7 +86,7 @@ class AppLocation(object):
         """
         # Check if we have a different data location.
         if Settings().contains('advanced/data path'):
-            path = Path(Settings().value('advanced/data path'))
+            path = Settings().value('advanced/data path')
         else:
             path = AppLocation.get_directory(AppLocation.DataDir)
             check_directory_exists(path)
@@ -118,7 +118,7 @@ class AppLocation(object):
         """
         Return the path a particular module stores its data under.
 
-        :type section: str
+        :param str section:
         :rtype: openlp.core.common.path.Path
         """
         path = AppLocation.get_data_path() / section
diff --git a/openlp/core/common/settings.py b/openlp/core/common/settings.py
index 8d12a69e5..1e6a120fa 100644
--- a/openlp/core/common/settings.py
+++ b/openlp/core/common/settings.py
@@ -24,15 +24,18 @@ This class contains the core default settings.
 """
 import datetime
 import logging
+import json
 import os
 
 from PyQt5 import QtCore, QtGui
 
-from openlp.core.common import ThemeLevel, SlideLimits, UiStrings, is_win, is_linux
-
+from openlp.core.common import SlideLimits, ThemeLevel, UiStrings, is_linux, is_win
+from openlp.core.common.json import OpenLPJsonDecoder, OpenLPJsonEncoder
+from openlp.core.common.path import Path, path_to_str, str_to_path
 
 log = logging.getLogger(__name__)
 
+__version__ = 2
 
 # Fix for bug #1014422.
 X11_BYPASS_DEFAULT = True
@@ -44,21 +47,6 @@ if is_linux():
         X11_BYPASS_DEFAULT = False
 
 
-def recent_files_conv(value):
-    """
-    If the value is not a list convert it to a list
-    :param value: Value to convert
-    :return: value as a List
-    """
-    if isinstance(value, list):
-        return value
-    elif isinstance(value, str):
-        return [value]
-    elif isinstance(value, bytes):
-        return [value.decode()]
-    return []
-
-
 def media_players_conv(string):
     """
     If phonon is in the setting string replace it with system
@@ -73,14 +61,24 @@ def media_players_conv(string):
     return string
 
 
+def file_names_conv(file_names):
+    """
+    Convert a list of file names in to a list of file paths.
+
+    :param list[str] file_names: The list of file names to convert.
+    :return: The list converted to file paths
+    :rtype: openlp.core.common.path.Path
+    """
+    return [str_to_path(file_name) for file_name in file_names]
+
+
 class Settings(QtCore.QSettings):
     """
     Class to wrap QSettings.
 
     * Exposes all the methods of QSettings.
-    * Adds functionality for OpenLP Portable. If the ``defaultFormat`` is set to
-      ``IniFormat``, and the path to the Ini file is set using ``set_filename``,
-      then the Settings constructor (without any arguments) will create a Settings
+    * Adds functionality for OpenLP Portable. If the ``defaultFormat`` is set to ``IniFormat``, and the path to the Ini
+      file is set using ``set_filename``, then the Settings constructor (without any arguments) will create a Settings
       object for accessing settings stored in that Ini file.
 
     ``__default_settings__``
@@ -91,7 +89,7 @@ class Settings(QtCore.QSettings):
 
             ('general/enable slide loop', 'advanced/slide limits', [(SlideLimits.Wrap, True), (SlideLimits.End, False)])
 
-        The first entry is the *old key*; it will be removed.
+        The first entry is the *old key*; if it is different from the *new key* it will be removed.
 
         The second entry is the *new key*; we will add it to the config. If this is just an empty string, we just remove
         the old key. The last entry is a list containing two-pair tuples. If the list is empty, no conversion is made.
@@ -105,11 +103,12 @@ class Settings(QtCore.QSettings):
         So, if the type of the old value is bool, then there must be two rules.
     """
     __default_settings__ = {
+        'settings/version': 0,
         'advanced/add page break': False,
         'advanced/alternate rows': not is_win(),
         'advanced/autoscrolling': {'dist': 1, 'pos': 0},
         'advanced/current media plugin': -1,
-        'advanced/data path': '',
+        'advanced/data path': None,
         # 7 stands for now, 0 to 6 is Monday to Sunday.
         'advanced/default service day': 7,
         'advanced/default service enabled': True,
@@ -143,7 +142,7 @@ class Settings(QtCore.QSettings):
         'api/authentication enabled': False,
         'api/ip address': '0.0.0.0',
         'api/thumbnails': True,
-        'crashreport/last directory': '',
+        'crashreport/last directory': None,
         'formattingTags/html_tags': '',
         'core/audio repeat list': False,
         'core/auto open': False,
@@ -162,7 +161,7 @@ class Settings(QtCore.QSettings):
         'core/screen blank': False,
         'core/show splash': True,
         'core/logo background color': '#ffffff',
-        'core/logo file': ':/graphics/openlp-splash-screen.png',
+        'core/logo file': Path(':/graphics/openlp-splash-screen.png'),
         'core/logo hide on startup': False,
         'core/songselect password': '',
         'core/songselect username': '',
@@ -177,17 +176,17 @@ class Settings(QtCore.QSettings):
         'media/players': 'system,webkit',
         'media/override player': QtCore.Qt.Unchecked,
         'players/background color': '#000000',
-        'servicemanager/last directory': '',
-        'servicemanager/last file': '',
-        'servicemanager/service theme': '',
+        'servicemanager/last directory': None,
+        'servicemanager/last file': None,
+        'servicemanager/service theme': None,
         'SettingsImport/file_date_created': datetime.datetime.now().strftime("%Y-%m-%d %H:%M"),
         'SettingsImport/Make_Changes': 'At_Own_RISK',
         'SettingsImport/type': 'OpenLP_settings_export',
         'SettingsImport/version': '',
         'themes/global theme': '',
-        'themes/last directory': '',
-        'themes/last directory export': '',
-        'themes/last directory import': '',
+        'themes/last directory': None,
+        'themes/last directory export': None,
+        'themes/last directory import': None,
         'themes/theme level': ThemeLevel.Song,
         'themes/wrap footer': False,
         'user interface/live panel': True,
@@ -208,22 +207,20 @@ class Settings(QtCore.QSettings):
         'projector/db database': '',
         'projector/enable': True,
         'projector/connect on start': False,
-        'projector/last directory import': '',
-        'projector/last directory export': '',
+        'projector/last directory import': None,
+        'projector/last directory export': None,
         'projector/poll time': 20,  # PJLink  timeout is 30 seconds
         'projector/socket timeout': 5,  # 5 second socket timeout
         'projector/source dialog type': 0  # Source select dialog box type
     }
     __file_path__ = ''
-    __obsolete_settings__ = [
+    __setting_upgrade_1__ = [
         # Changed during 2.2.x development.
-        # ('advanced/stylesheet fix', '', []),
-        # ('general/recent files', 'core/recent files', [(recent_files_conv, None)]),
         ('songs/search as type', 'advanced/search as type', []),
         ('media/players', 'media/players_temp', [(media_players_conv, None)]),  # Convert phonon to system
         ('media/players_temp', 'media/players', []),  # Move temp setting from above to correct setting
         ('advanced/default color', 'core/logo background color', []),  # Default image renamed + moved to general > 2.4.
-        ('advanced/default image', '/core/logo file', []),  # Default image renamed + moved to general after 2.4.
+        ('advanced/default image', 'core/logo file', []),  # Default image renamed + moved to general after 2.4.
         ('remotes/https enabled', '', []),
         ('remotes/https port', '', []),
         ('remotes/twelve hour', 'api/twelve hour', []),
@@ -234,7 +231,6 @@ class Settings(QtCore.QSettings):
         ('remotes/authentication enabled', 'api/authentication enabled', []),
         ('remotes/ip address', 'api/ip address', []),
         ('remotes/thumbnails', 'api/thumbnails', []),
-        ('advanced/default image', 'core/logo file', []),  # Default image renamed + moved to general after 2.4.
         ('shortcuts/escapeItem', 'shortcuts/desktopScreenEnable', []),  # Escape item was removed in 2.6.
         ('shortcuts/offlineHelpItem', 'shortcuts/userManualItem', []),  # Online and Offline help were combined in 2.6.
         ('shortcuts/onlineHelpItem', 'shortcuts/userManualItem', []),  # Online and Offline help were combined in 2.6.
@@ -243,7 +239,28 @@ class Settings(QtCore.QSettings):
         # Last search type was renamed to last used search type in 2.6 since Bible search value type changed in 2.6.
         ('songs/last search type', 'songs/last used search type', []),
         ('bibles/last search type', '', []),
-        ('custom/last search type', 'custom/last used search type', [])
+        ('custom/last search type', 'custom/last used search type', [])]
+
+    __setting_upgrade_2__ = [
+        # The following changes are being made for the conversion to using Path objects made in 2.6 development
+        ('advanced/data path', 'advanced/data path', [(str_to_path, None)]),
+        ('crashreport/last directory', 'crashreport/last directory', [(str_to_path, None)]),
+        ('servicemanager/last directory', 'servicemanager/last directory', [(str_to_path, None)]),
+        ('servicemanager/last file', 'servicemanager/last file', [(str_to_path, None)]),
+        ('themes/last directory', 'themes/last directory', [(str_to_path, None)]),
+        ('themes/last directory export', 'themes/last directory export', [(str_to_path, None)]),
+        ('themes/last directory import', 'themes/last directory import', [(str_to_path, None)]),
+        ('projector/last directory import', 'projector/last directory import', [(str_to_path, None)]),
+        ('projector/last directory export', 'projector/last directory export', [(str_to_path, None)]),
+        ('bibles/last directory import', 'bibles/last directory import', [(str_to_path, None)]),
+        ('presentations/pdf_program', 'presentations/pdf_program', [(str_to_path, None)]),
+        ('songs/last directory import', 'songs/last directory import', [(str_to_path, None)]),
+        ('songs/last directory export', 'songs/last directory export', [(str_to_path, None)]),
+        ('songusage/last directory export', 'songusage/last directory export', [(str_to_path, None)]),
+        ('core/recent files', 'core/recent files', [(file_names_conv, None)]),
+        ('media/media files', 'media/media files', [(file_names_conv, None)]),
+        ('presentations/presentations files', 'presentations/presentations files', [(file_names_conv, None)]),
+        ('core/logo file', 'core/logo file', [(str_to_path, None)])
     ]
 
     @staticmethod
@@ -256,13 +273,16 @@ class Settings(QtCore.QSettings):
         Settings.__default_settings__.update(default_values)
 
     @staticmethod
-    def set_filename(ini_file):
+    def set_filename(ini_path):
         """
         Sets the complete path to an Ini file to be used by Settings objects.
 
         Does not affect existing Settings objects.
+
+        :param openlp.core.common.path.Path ini_path: ini file path
+        :rtype: None
         """
-        Settings.__file_path__ = ini_file
+        Settings.__file_path__ = str(ini_path)
 
     @staticmethod
     def set_up_default_values():
@@ -431,14 +451,22 @@ class Settings(QtCore.QSettings):
             key = self.group() + '/' + key
         return Settings.__default_settings__[key]
 
-    def remove_obsolete_settings(self):
+    def upgrade_settings(self):
         """
         This method is only called to clean up the config. It removes old settings and it renames settings. See
         ``__obsolete_settings__`` for more details.
         """
-        for old_key, new_key, rules in Settings.__obsolete_settings__:
-            # Once removed we don't have to do this again.
-            if self.contains(old_key):
+        current_version = self.value('settings/version')
+        if __version__ == current_version:
+            return
+        for version in range(current_version, __version__):
+            version += 1
+            upgrade_list = getattr(self, '__setting_upgrade_{version}__'.format(version=version))
+            for old_key, new_key, rules in upgrade_list:
+                # Once removed we don't have to do this again. - Can be removed once fully switched to the versioning
+                # system.
+                if not self.contains(old_key):
+                    continue
                 if new_key:
                     # Get the value of the old_key.
                     old_value = super(Settings, self).value(old_key)
@@ -457,14 +485,17 @@ class Settings(QtCore.QSettings):
                             old_value = new
                             break
                     self.setValue(new_key, old_value)
-                self.remove(old_key)
+                if new_key != old_key:
+                    self.remove(old_key)
+        self.setValue('settings/version', version)
 
     def value(self, key):
         """
         Returns the value for the given ``key``. The returned ``value`` is of the same type as the default value in the
         *Settings.__default_settings__* dict.
 
-        :param key: The key to return the value from.
+        :param str key: The key to return the value from.
+        :return: The value stored by the setting.
         """
         # if group() is not empty the group has not been specified together with the key.
         if self.group():
@@ -474,6 +505,18 @@ class Settings(QtCore.QSettings):
         setting = super(Settings, self).value(key, default_value)
         return self._convert_value(setting, default_value)
 
+    def setValue(self, key, value):
+        """
+        Reimplement the setValue method to handle Path objects.
+
+        :param str key: The key of the setting to save
+        :param value: The value to save
+        :rtype: None
+        """
+        if isinstance(value, Path) or (isinstance(value, list) and value and isinstance(value[0], Path)):
+            value = json.dumps(value, cls=OpenLPJsonEncoder)
+        super().setValue(key, value)
+
     def _convert_value(self, setting, default_value):
         """
         This converts the given ``setting`` to the type of the given ``default_value``.
@@ -491,8 +534,11 @@ class Settings(QtCore.QSettings):
             if isinstance(default_value, str):
                 return ''
             # An empty list saved to the settings results in a None type being returned.
-            else:
+            elif isinstance(default_value, list):
                 return []
+        elif isinstance(setting, str):
+            if '__Path__' in setting:
+                return json.loads(setting, cls=OpenLPJsonDecoder)
         # Convert the setting to the correct type.
         if isinstance(default_value, bool):
             if isinstance(setting, bool):
diff --git a/openlp/core/lib/mediamanageritem.py b/openlp/core/lib/mediamanageritem.py
index 6b04d076b..59a0e4e33 100644
--- a/openlp/core/lib/mediamanageritem.py
+++ b/openlp/core/lib/mediamanageritem.py
@@ -29,7 +29,7 @@ import re
 from PyQt5 import QtCore, QtWidgets
 
 from openlp.core.common import Registry, RegistryProperties, Settings, UiStrings, translate
-from openlp.core.common.path import path_to_str, str_to_path
+from openlp.core.common.path import Path, path_to_str, str_to_path
 from openlp.core.lib import ServiceItem, StringContent, ServiceItemContext
 from openlp.core.lib.searchedit import SearchEdit
 from openlp.core.lib.ui import create_widget_action, critical_error_message_box
@@ -313,7 +313,7 @@ class MediaManagerItem(QtWidgets.QWidget, RegistryProperties):
         """
         file_paths, selected_filter = FileDialog.getOpenFileNames(
             self, self.on_new_prompt,
-            str_to_path(Settings().value(self.settings_section + '/last directory')),
+            Settings().value(self.settings_section + '/last directory'),
             self.on_new_file_masks)
         log.info('New files(s) {file_paths}'.format(file_paths=file_paths))
         if file_paths:
@@ -377,9 +377,8 @@ class MediaManagerItem(QtWidgets.QWidget, RegistryProperties):
                 self.list_view.clear()
             self.load_list(full_list, target_group)
             last_dir = os.path.split(files[0])[0]
-            Settings().setValue(self.settings_section + '/last directory', last_dir)
-            Settings().setValue('{section}/{section} files'.format(section=self.settings_section),
-                                self.get_file_list())
+            Settings().setValue(self.settings_section + '/last directory', Path(last_dir))
+            Settings().setValue('{section}/{section} files'.format(section=self.settings_section), self.get_file_list())
         if duplicates_found:
             critical_error_message_box(UiStrings().Duplicate,
                                        translate('OpenLP.MediaManagerItem',
@@ -400,13 +399,15 @@ class MediaManagerItem(QtWidgets.QWidget, RegistryProperties):
     def get_file_list(self):
         """
         Return the current list of files
+
+        :rtype: list[openlp.core.common.path.Path]
         """
-        file_list = []
+        file_paths = []
         for index in range(self.list_view.count()):
             list_item = self.list_view.item(index)
             filename = list_item.data(QtCore.Qt.UserRole)
-            file_list.append(filename)
-        return file_list
+            file_paths.append(str_to_path(filename))
+        return file_paths
 
     def load_list(self, load_list, target_group):
         """
diff --git a/openlp/core/lib/plugin.py b/openlp/core/lib/plugin.py
index b06e0fbd4..1b1cddfea 100644
--- a/openlp/core/lib/plugin.py
+++ b/openlp/core/lib/plugin.py
@@ -150,7 +150,7 @@ class Plugin(QtCore.QObject, RegistryProperties):
         self.status = PluginStatus.Inactive
         # Add the default status to the default settings.
         default_settings[name + '/status'] = PluginStatus.Inactive
-        default_settings[name + '/last directory'] = ''
+        default_settings[name + '/last directory'] = None
         # Append a setting for files in the mediamanager (note not all plugins
         # which have a mediamanager need this).
         if media_item_class is not None:
diff --git a/openlp/core/ui/exceptionform.py b/openlp/core/ui/exceptionform.py
index 349352d92..00a7c89e2 100644
--- a/openlp/core/ui/exceptionform.py
+++ b/openlp/core/ui/exceptionform.py
@@ -70,9 +70,9 @@ try:
 except ImportError:
     VLC_VERSION = '-'
 
-from openlp.core.common import Settings, UiStrings, translate
+from openlp.core.common import RegistryProperties, Settings, UiStrings, is_linux, translate
 from openlp.core.common.versionchecker import get_application_version
-from openlp.core.common import RegistryProperties, is_linux
+from openlp.core.ui.lib.filedialog import FileDialog
 
 from .exceptiondialog import Ui_ExceptionDialog
 
@@ -139,17 +139,17 @@ class ExceptionForm(QtWidgets.QDialog, Ui_ExceptionDialog, RegistryProperties):
         """
         Saving exception log and system information to a file.
         """
-        filename = QtWidgets.QFileDialog.getSaveFileName(
+        file_path, filter_used = FileDialog.getSaveFileName(
             self,
             translate('OpenLP.ExceptionForm', 'Save Crash Report'),
             Settings().value(self.settings_section + '/last directory'),
-            translate('OpenLP.ExceptionForm', 'Text files (*.txt *.log *.text)'))[0]
-        if filename:
-            filename = str(filename).replace('/', os.path.sep)
-            Settings().setValue(self.settings_section + '/last directory', os.path.dirname(filename))
+            translate('OpenLP.ExceptionForm', 'Text files (*.txt *.log *.text)'))
+        if file_path:
+            Settings().setValue(self.settings_section + '/last directory', file_path.parent)
             opts = self._create_report()
             report_text = self.report_text.format(version=opts['version'], description=opts['description'],
                                                   traceback=opts['traceback'], libs=opts['libs'], system=opts['system'])
+            filename = str(file_path)
             try:
                 report_file = open(filename, 'w')
                 try:
@@ -212,17 +212,16 @@ class ExceptionForm(QtWidgets.QDialog, Ui_ExceptionDialog, RegistryProperties):
 
     def on_attach_file_button_clicked(self):
         """
-        Attache files to the bug report e-mail.
+        Attach files to the bug report e-mail.
         """
-        files, filter_used = QtWidgets.QFileDialog.getOpenFileName(self,
-                                                                   translate('ImagePlugin.ExceptionDialog',
-                                                                             'Select Attachment'),
-                                                                   Settings().value(self.settings_section +
-                                                                                    '/last directory'),
-                                                                   '{text} (*)'.format(text=UiStrings().AllFiles))
-        log.info('New files(s) {files}'.format(files=str(files)))
-        if files:
-            self.file_attachment = str(files)
+        file_path, filter_used = \
+            FileDialog.getOpenFileName(self,
+                                       translate('ImagePlugin.ExceptionDialog', 'Select Attachment'),
+                                       Settings().value(self.settings_section + '/last directory'),
+                                       '{text} (*)'.format(text=UiStrings().AllFiles))
+        log.info('New file {file}'.format(file=file_path))
+        if file_path:
+            self.file_attachment = str(file_path)
 
     def __button_state(self, state):
         """
diff --git a/openlp/core/ui/generaltab.py b/openlp/core/ui/generaltab.py
index 6160aa622..70a7ddf5f 100644
--- a/openlp/core/ui/generaltab.py
+++ b/openlp/core/ui/generaltab.py
@@ -293,7 +293,7 @@ class GeneralTab(SettingsTab):
         self.auto_open_check_box.setChecked(settings.value('auto open'))
         self.show_splash_check_box.setChecked(settings.value('show splash'))
         self.logo_background_color = settings.value('logo background color')
-        self.logo_file_path_edit.path = str_to_path(settings.value('logo file'))
+        self.logo_file_path_edit.path = settings.value('logo file')
         self.logo_hide_on_startup_check_box.setChecked(settings.value('logo hide on startup'))
         self.logo_color_button.color = self.logo_background_color
         self.check_for_updates_check_box.setChecked(settings.value('update check'))
@@ -327,7 +327,7 @@ class GeneralTab(SettingsTab):
         settings.setValue('auto open', self.auto_open_check_box.isChecked())
         settings.setValue('show splash', self.show_splash_check_box.isChecked())
         settings.setValue('logo background color', self.logo_background_color)
-        settings.setValue('logo file', path_to_str(self.logo_file_path_edit.path))
+        settings.setValue('logo file', self.logo_file_path_edit.path)
         settings.setValue('logo hide on startup', self.logo_hide_on_startup_check_box.isChecked())
         settings.setValue('update check', self.check_for_updates_check_box.isChecked())
         settings.setValue('save prompt', self.save_check_service_check_box.isChecked())
diff --git a/openlp/core/ui/lib/wizard.py b/openlp/core/ui/lib/wizard.py
index 936682585..8f3093fef 100644
--- a/openlp/core/ui/lib/wizard.py
+++ b/openlp/core/ui/lib/wizard.py
@@ -30,6 +30,7 @@ from PyQt5 import QtCore, QtGui, QtWidgets
 from openlp.core.common import Registry, RegistryProperties, Settings, UiStrings, translate, is_macosx
 from openlp.core.lib import build_icon
 from openlp.core.lib.ui import add_welcome_page
+from openlp.core.ui.lib.filedialog import FileDialog
 
 log = logging.getLogger(__name__)
 
@@ -278,37 +279,38 @@ class OpenLPWizard(QtWidgets.QWizard, RegistryProperties):
 
     def get_file_name(self, title, editbox, setting_name, filters=''):
         """
-        Opens a QFileDialog and saves the filename to the given editbox.
+        Opens a FileDialog and saves the filename to the given editbox.
 
-        :param title: The title of the dialog (unicode).
-        :param editbox:  An editbox (QLineEdit).
-        :param setting_name: The place where to save the last opened directory.
-        :param filters: The file extension filters. It should contain the file description
+        :param str title: The title of the dialog.
+        :param QtWidgets.QLineEdit editbox:  An QLineEdit.
+        :param str setting_name: The place where to save the last opened directory.
+        :param str filters: The file extension filters. It should contain the file description
             as well as the file extension. For example::
 
                 'OpenLP 2 Databases (*.sqlite)'
+        :rtype: None
         """
         if filters:
             filters += ';;'
         filters += '%s (*)' % UiStrings().AllFiles
-        filename, filter_used = QtWidgets.QFileDialog.getOpenFileName(
-            self, title, os.path.dirname(Settings().value(self.plugin.settings_section + '/' + setting_name)),
-            filters)
-        if filename:
-            editbox.setText(filename)
-        Settings().setValue(self.plugin.settings_section + '/' + setting_name, filename)
+        file_path, filter_used = FileDialog.getOpenFileName(
+            self, title, Settings().value(self.plugin.settings_section + '/' + setting_name), filters)
+        if file_path:
+            editbox.setText(str(file_path))
+            Settings().setValue(self.plugin.settings_section + '/' + setting_name, file_path.parent)
 
     def get_folder(self, title, editbox, setting_name):
         """
-        Opens a QFileDialog and saves the selected folder to the given editbox.
+        Opens a FileDialog and saves the selected folder to the given editbox.
 
-        :param title: The title of the dialog (unicode).
-        :param editbox: An editbox (QLineEdit).
-        :param setting_name: The place where to save the last opened directory.
+        :param str title: The title of the dialog.
+        :param QtWidgets.QLineEdit editbox: An QLineEditbox.
+        :param str setting_name: The place where to save the last opened directory.
+        :rtype: None
         """
-        folder = QtWidgets.QFileDialog.getExistingDirectory(
+        folder_path = FileDialog.getExistingDirectory(
             self, title, Settings().value(self.plugin.settings_section + '/' + setting_name),
             QtWidgets.QFileDialog.ShowDirsOnly)
-        if folder:
-            editbox.setText(folder)
-        Settings().setValue(self.plugin.settings_section + '/' + setting_name, folder)
+        if folder_path:
+            editbox.setText(str(folder_path))
+            Settings().setValue(self.plugin.settings_section + '/' + setting_name, folder_path)
diff --git a/openlp/core/ui/maindisplay.py b/openlp/core/ui/maindisplay.py
index e846898b5..7b0caaa98 100644
--- a/openlp/core/ui/maindisplay.py
+++ b/openlp/core/ui/maindisplay.py
@@ -37,6 +37,7 @@ from PyQt5 import QtCore, QtWidgets, QtWebKit, QtWebKitWidgets, QtGui, QtMultime
 
 from openlp.core.common import AppLocation, Registry, RegistryProperties, OpenLPMixin, Settings, translate,\
     is_macosx, is_win
+from openlp.core.common.path import path_to_str
 from openlp.core.lib import ServiceItem, ImageSource, ScreenList, build_html, expand_tags, image_to_byte
 from openlp.core.lib.theme import BackgroundType
 from openlp.core.ui import HideMode, AlertLocation, DisplayControllerType
@@ -259,7 +260,7 @@ class MainDisplay(OpenLPMixin, Display, RegistryProperties):
             background_color.setNamedColor(Settings().value('core/logo background color'))
             if not background_color.isValid():
                 background_color = QtCore.Qt.white
-            image_file = Settings().value('core/logo file')
+            image_file = path_to_str(Settings().value('core/logo file'))
             splash_image = QtGui.QImage(image_file)
             self.initial_fame = QtGui.QImage(
                 self.screen['size'].width(),
diff --git a/openlp/core/ui/mainwindow.py b/openlp/core/ui/mainwindow.py
index 9e9edde33..023d1799d 100644
--- a/openlp/core/ui/mainwindow.py
+++ b/openlp/core/ui/mainwindow.py
@@ -39,7 +39,7 @@ from openlp.core.api.http import server
 from openlp.core.common import Registry, RegistryProperties, AppLocation, LanguageManager, Settings, UiStrings, \
     check_directory_exists, translate, is_win, is_macosx, add_actions
 from openlp.core.common.actions import ActionList, CategoryOrder
-from openlp.core.common.path import Path
+from openlp.core.common.path import Path, path_to_str, str_to_path
 from openlp.core.common.versionchecker import get_application_version
 from openlp.core.lib import Renderer, PluginManager, ImageManager, PluginStatus, ScreenList, build_icon
 from openlp.core.lib.ui import create_action
@@ -879,8 +879,8 @@ class MainWindow(QtWidgets.QMainWindow, Ui_MainWindow, RegistryProperties):
         # Convert image files
         log.info('hook upgrade_plugin_settings')
         self.plugin_manager.hook_upgrade_plugin_settings(import_settings)
-        # Remove/rename old settings to prepare the import.
-        import_settings.remove_obsolete_settings()
+        # Upgrade settings to prepare the import.
+        import_settings.upgrade_settings()
         # Lets do a basic sanity check. If it contains this string we can assume it was created by OpenLP and so we'll
         # load what we can from it, and just silently ignore anything we don't recognise.
         if import_settings.value('SettingsImport/type') != 'OpenLP_settings_export':
@@ -1277,7 +1277,7 @@ class MainWindow(QtWidgets.QMainWindow, Ui_MainWindow, RegistryProperties):
         settings.remove('custom slide')
         settings.remove('service')
         settings.beginGroup(self.general_settings_section)
-        self.recent_files = settings.value('recent files')
+        self.recent_files = [path_to_str(file_path) for file_path in settings.value('recent files')]
         settings.endGroup()
         settings.beginGroup(self.ui_settings_section)
         self.move(settings.value('main window position'))
@@ -1301,7 +1301,7 @@ class MainWindow(QtWidgets.QMainWindow, Ui_MainWindow, RegistryProperties):
         log.debug('Saving QSettings')
         settings = Settings()
         settings.beginGroup(self.general_settings_section)
-        settings.setValue('recent files', self.recent_files)
+        settings.setValue('recent files', [str_to_path(file) for file in self.recent_files])
         settings.endGroup()
         settings.beginGroup(self.ui_settings_section)
         settings.setValue('main window position', self.pos())
@@ -1443,7 +1443,7 @@ class MainWindow(QtWidgets.QMainWindow, Ui_MainWindow, RegistryProperties):
             log.info('No data copy requested')
         # Change the location of data directory in config file.
         settings = QtCore.QSettings()
-        settings.setValue('advanced/data path', self.new_data_path)
+        settings.setValue('advanced/data path', Path(self.new_data_path))
         # Check if the new data path is our default.
         if self.new_data_path == str(AppLocation.get_directory(AppLocation.DataDir)):
             settings.remove('advanced/data path')
diff --git a/openlp/core/ui/servicemanager.py b/openlp/core/ui/servicemanager.py
index 519378e75..5051e43c1 100644
--- a/openlp/core/ui/servicemanager.py
+++ b/openlp/core/ui/servicemanager.py
@@ -35,12 +35,13 @@ from PyQt5 import QtCore, QtGui, QtWidgets
 from openlp.core.common import Registry, RegistryProperties, AppLocation, Settings, ThemeLevel, OpenLPMixin, \
     RegistryMixin, check_directory_exists, UiStrings, translate, split_filename, delete_file
 from openlp.core.common.actions import ActionList, CategoryOrder
-from openlp.core.common.path import Path
+from openlp.core.common.languagemanager import format_time
+from openlp.core.common.path import Path, path_to_str, str_to_path
 from openlp.core.lib import ServiceItem, ItemCapabilities, PluginStatus, build_icon
 from openlp.core.lib.ui import critical_error_message_box, create_widget_action, find_and_set_in_combo_box
 from openlp.core.ui import ServiceNoteForm, ServiceItemEditForm, StartTimeForm
 from openlp.core.ui.lib import OpenLPToolbar
-from openlp.core.common.languagemanager import format_time
+from openlp.core.ui.lib.filedialog import FileDialog
 
 
 class ServiceManagerList(QtWidgets.QTreeWidget):
@@ -373,7 +374,7 @@ class ServiceManager(OpenLPMixin, RegistryMixin, QtWidgets.QWidget, Ui_ServiceMa
         """
         self._file_name = str(file_name)
         self.main_window.set_service_modified(self.is_modified(), self.short_file_name())
-        Settings().setValue('servicemanager/last file', file_name)
+        Settings().setValue('servicemanager/last file', Path(file_name))
         self._save_lite = self._file_name.endswith('.oszl')
 
     def file_name(self):
@@ -435,18 +436,17 @@ class ServiceManager(OpenLPMixin, RegistryMixin, QtWidgets.QWidget, Ui_ServiceMa
             elif result == QtWidgets.QMessageBox.Save:
                 self.decide_save_method()
         if not load_file:
-            file_name, filter_used = QtWidgets.QFileDialog.getOpenFileName(
+            file_path, filter_used = FileDialog.getOpenFileName(
                 self.main_window,
                 translate('OpenLP.ServiceManager', 'Open File'),
                 Settings().value(self.main_window.service_manager_settings_section + '/last directory'),
                 translate('OpenLP.ServiceManager', 'OpenLP Service Files (*.osz *.oszl)'))
-            if not file_name:
+            if not file_path:
                 return False
         else:
-            file_name = load_file
-        Settings().setValue(self.main_window.service_manager_settings_section + '/last directory',
-                            split_filename(file_name)[0])
-        self.load_file(file_name)
+            file_path = str_to_path(load_file)
+        Settings().setValue(self.main_window.service_manager_settings_section + '/last directory', file_path.parent)
+        self.load_file(str(file_path))
 
     def save_modified_service(self):
         """
@@ -477,7 +477,7 @@ class ServiceManager(OpenLPMixin, RegistryMixin, QtWidgets.QWidget, Ui_ServiceMa
         self.set_file_name('')
         self.service_id += 1
         self.set_modified(False)
-        Settings().setValue('servicemanager/last file', '')
+        Settings().setValue('servicemanager/last file', None)
         self.plugin_manager.new_service_created()
 
     def create_basic_service(self):
@@ -513,7 +513,7 @@ class ServiceManager(OpenLPMixin, RegistryMixin, QtWidgets.QWidget, Ui_ServiceMa
         base_name = os.path.splitext(file_name)[0]
         service_file_name = '{name}.osj'.format(name=base_name)
         self.log_debug('ServiceManager.save_file - {name}'.format(name=path_file_name))
-        Settings().setValue(self.main_window.service_manager_settings_section + '/last directory', path)
+        Settings().setValue(self.main_window.service_manager_settings_section + '/last directory', Path(path))
         service = self.create_basic_service()
         write_list = []
         missing_list = []
@@ -634,7 +634,7 @@ class ServiceManager(OpenLPMixin, RegistryMixin, QtWidgets.QWidget, Ui_ServiceMa
         base_name = os.path.splitext(file_name)[0]
         service_file_name = '{name}.osj'.format(name=base_name)
         self.log_debug('ServiceManager.save_file - {name}'.format(name=path_file_name))
-        Settings().setValue(self.main_window.service_manager_settings_section + '/last directory', path)
+        Settings().setValue(self.main_window.service_manager_settings_section + '/last directory', Path(path))
         service = self.create_basic_service()
         self.application.set_busy_cursor()
         # Number of items + 1 to zip it
@@ -695,7 +695,7 @@ class ServiceManager(OpenLPMixin, RegistryMixin, QtWidgets.QWidget, Ui_ServiceMa
             default_file_name = format_time(default_pattern, local_time)
         else:
             default_file_name = ''
-        directory = Settings().value(self.main_window.service_manager_settings_section + '/last directory')
+        directory = path_to_str(Settings().value(self.main_window.service_manager_settings_section + '/last directory'))
         path = os.path.join(directory, default_file_name)
         # 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.
@@ -778,7 +778,7 @@ class ServiceManager(OpenLPMixin, RegistryMixin, QtWidgets.QWidget, Ui_ServiceMa
                 delete_file(Path(p_file))
                 self.main_window.add_recent_file(file_name)
                 self.set_modified(False)
-                Settings().setValue('servicemanager/last file', file_name)
+                Settings().setValue('servicemanager/last file', Path(file_name))
             else:
                 critical_error_message_box(message=translate('OpenLP.ServiceManager', 'File is not a valid service.'))
                 self.log_error('File contains no service data')
@@ -843,7 +843,7 @@ class ServiceManager(OpenLPMixin, RegistryMixin, QtWidgets.QWidget, Ui_ServiceMa
         Load the last service item from the service manager when the service was last closed. Can be blank if there was
         no service present.
         """
-        file_name = Settings().value('servicemanager/last file')
+        file_name = str_to_path(Settings().value('servicemanager/last file'))
         if file_name:
             self.load_file(file_name)
 
diff --git a/openlp/core/ui/thememanager.py b/openlp/core/ui/thememanager.py
index 776926b7a..f32118f95 100644
--- a/openlp/core/ui/thememanager.py
+++ b/openlp/core/ui/thememanager.py
@@ -378,16 +378,16 @@ class ThemeManager(OpenLPMixin, RegistryMixin, QtWidgets.QWidget, Ui_ThemeManage
             critical_error_message_box(message=translate('OpenLP.ThemeManager', 'You have not selected a theme.'))
             return
         theme = item.data(QtCore.Qt.UserRole)
-        path, filter_used = \
-            QtWidgets.QFileDialog.getSaveFileName(self.main_window,
-                                                  translate('OpenLP.ThemeManager', 'Save Theme - ({name})').
-                                                  format(name=theme),
-                                                  Settings().value(self.settings_section + '/last directory export'),
-                                                  translate('OpenLP.ThemeManager', 'OpenLP Themes (*.otz)'))
+        export_path, filter_used = \
+            FileDialog.getSaveFileName(self.main_window,
+                                       translate('OpenLP.ThemeManager', 'Save Theme - ({name})').
+                                       format(name=theme),
+                                       Settings().value(self.settings_section + '/last directory export'),
+                                       translate('OpenLP.ThemeManager', 'OpenLP Themes (*.otz)'))
         self.application.set_busy_cursor()
-        if path:
-            Settings().setValue(self.settings_section + '/last directory export', path)
-            if self._export_theme(path, theme):
+        if export_path:
+            Settings().setValue(self.settings_section + '/last directory export', export_path.parent)
+            if self._export_theme(str(export_path, theme)):
                 QtWidgets.QMessageBox.information(self,
                                                   translate('OpenLP.ThemeManager', 'Theme Exported'),
                                                   translate('OpenLP.ThemeManager',
@@ -428,16 +428,15 @@ class ThemeManager(OpenLPMixin, RegistryMixin, QtWidgets.QWidget, Ui_ThemeManage
         file_paths, selected_filter = FileDialog.getOpenFileNames(
             self,
             translate('OpenLP.ThemeManager', 'Select Theme Import File'),
-            str_to_path(Settings().value(self.settings_section + '/last directory import')),
+            Settings().value(self.settings_section + '/last directory import'),
             translate('OpenLP.ThemeManager', 'OpenLP Themes (*.otz)'))
         self.log_info('New Themes {file_paths}'.format(file_paths=file_paths))
         if not file_paths:
             return
         self.application.set_busy_cursor()
         for file_path in file_paths:
-            file_name = path_to_str(file_path)
-            Settings().setValue(self.settings_section + '/last directory import', str(file_name))
-            self.unzip_theme(file_name, self.path)
+            self.unzip_theme(path_to_str(file_path), self.path)
+        Settings().setValue(self.settings_section + '/last directory import', file_path)
         self.load_themes()
         self.application.set_normal_cursor()
 
diff --git a/openlp/plugins/bibles/bibleplugin.py b/openlp/plugins/bibles/bibleplugin.py
index bcc81f9cb..4829ff234 100644
--- a/openlp/plugins/bibles/bibleplugin.py
+++ b/openlp/plugins/bibles/bibleplugin.py
@@ -59,7 +59,7 @@ __default_settings__ = {
     'bibles/range separator': '',
     'bibles/list separator': '',
     'bibles/end separator': '',
-    'bibles/last directory import': '',
+    'bibles/last directory import': None,
     'bibles/hide combined quick error': False,
     'bibles/is search while typing enabled': True
 }
diff --git a/openlp/plugins/images/lib/mediaitem.py b/openlp/plugins/images/lib/mediaitem.py
index 9c69c8ac5..bcf222eb0 100644
--- a/openlp/plugins/images/lib/mediaitem.py
+++ b/openlp/plugins/images/lib/mediaitem.py
@@ -390,7 +390,7 @@ class ImageMediaItem(MediaManagerItem):
         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', last_dir)
+        Settings().setValue(self.settings_section + '/last directory', Path(last_dir))
 
     def load_list(self, images, target_group=None, initial_load=False):
         """
diff --git a/openlp/plugins/media/lib/mediaitem.py b/openlp/plugins/media/lib/mediaitem.py
index f004b27a1..154d033c1 100644
--- a/openlp/plugins/media/lib/mediaitem.py
+++ b/openlp/plugins/media/lib/mediaitem.py
@@ -27,7 +27,7 @@ from PyQt5 import QtCore, QtWidgets
 
 from openlp.core.common import Registry, RegistryProperties, AppLocation, Settings, check_directory_exists, UiStrings,\
     translate
-from openlp.core.common.path import Path
+from openlp.core.common.path import Path, path_to_str, str_to_path
 from openlp.core.lib import ItemCapabilities, MediaManagerItem, MediaType, ServiceItem, ServiceItemContext, \
     build_icon, check_item_selected
 from openlp.core.lib.ui import create_widget_action, critical_error_message_box, create_horizontal_adjusting_combo_box
@@ -303,7 +303,7 @@ class MediaMediaItem(MediaManagerItem, RegistryProperties):
         self.list_view.clear()
         self.service_path = os.path.join(str(AppLocation.get_section_data_path(self.settings_section)), 'thumbnails')
         check_directory_exists(Path(self.service_path))
-        self.load_list(Settings().value(self.settings_section + '/media files'))
+        self.load_list([path_to_str(file) for file in Settings().value(self.settings_section + '/media files')])
         self.rebuild_players()
 
     def rebuild_players(self):
@@ -401,14 +401,14 @@ class MediaMediaItem(MediaManagerItem, RegistryProperties):
         :param media_type: Type to get, defaults to audio.
         :return: The media list
         """
-        media = Settings().value(self.settings_section + '/media files')
-        media.sort(key=lambda filename: get_locale_key(os.path.split(str(filename))[1]))
+        media_file_paths = Settings().value(self.settings_section + '/media files')
+        media_file_paths.sort(key=lambda file_path: get_locale_key(file_path.name))
         if media_type == MediaType.Audio:
             extension = self.media_controller.audio_extensions_list
         else:
             extension = self.media_controller.video_extensions_list
         extension = [x[1:] for x in extension]
-        media = [x for x in media if os.path.splitext(x)[1] in extension]
+        media = [x for x in media_file_paths if x.suffix in extension]
         return media
 
     def search(self, string, show_error):
@@ -419,13 +419,12 @@ class MediaMediaItem(MediaManagerItem, RegistryProperties):
         :param show_error: Should the error be shown (True)
         :return: The search result.
         """
-        files = Settings().value(self.settings_section + '/media files')
         results = []
         string = string.lower()
-        for file in files:
-            filename = os.path.split(str(file))[1]
-            if filename.lower().find(string) > -1:
-                results.append([file, filename])
+        for file_path in Settings().value(self.settings_section + '/media files'):
+            file_name = file_path.name
+            if file_name.lower().find(string) > -1:
+                results.append([str(file_path), file_name])
         return results
 
     def on_load_optical(self):
@@ -446,13 +445,13 @@ class MediaMediaItem(MediaManagerItem, RegistryProperties):
 
         :param optical: The clip to add.
         """
-        full_list = self.get_file_list()
+        file_paths = self.get_file_list()
         # If the clip already is in the media list it isn't added and an error message is displayed.
-        if optical in full_list:
+        if optical in file_paths:
             critical_error_message_box(translate('MediaPlugin.MediaItem', 'Mediaclip already saved'),
                                        translate('MediaPlugin.MediaItem', 'This mediaclip has already been saved'))
             return
         # Append the optical string to the media list
-        full_list.append(optical)
+        file_paths.append(optical)
         self.load_list([optical])
-        Settings().setValue(self.settings_section + '/media files', self.get_file_list())
+        Settings().setValue(self.settings_section + '/media files', file_paths)
diff --git a/openlp/plugins/presentations/lib/mediaitem.py b/openlp/plugins/presentations/lib/mediaitem.py
index 9e2921667..99c937eb0 100644
--- a/openlp/plugins/presentations/lib/mediaitem.py
+++ b/openlp/plugins/presentations/lib/mediaitem.py
@@ -26,10 +26,11 @@ import os
 from PyQt5 import QtCore, QtGui, QtWidgets
 
 from openlp.core.common import Registry, Settings, UiStrings, translate
+from openlp.core.common.languagemanager import get_locale_key
+from openlp.core.common.path import path_to_str
 from openlp.core.lib import MediaManagerItem, ItemCapabilities, ServiceItemContext,\
     build_icon, check_item_selected, create_thumb, validate_thumb
 from openlp.core.lib.ui import critical_error_message_box, create_horizontal_adjusting_combo_box
-from openlp.core.common.languagemanager import get_locale_key
 from openlp.plugins.presentations.lib import MessageListener
 from openlp.plugins.presentations.lib.pdfcontroller import PDF_CONTROLLER_FILETYPES
 
@@ -126,8 +127,8 @@ class PresentationMediaItem(MediaManagerItem):
         Populate the media manager tab
         """
         self.list_view.setIconSize(QtCore.QSize(88, 50))
-        files = Settings().value(self.settings_section + '/presentations files')
-        self.load_list(files, initial_load=True)
+        file_paths = Settings().value(self.settings_section + '/presentations files')
+        self.load_list([path_to_str(file) for file in file_paths], initial_load=True)
         self.populate_display_types()
 
     def populate_display_types(self):
@@ -157,7 +158,7 @@ class PresentationMediaItem(MediaManagerItem):
         existing files, and when the user adds new files via the media manager.
         """
         current_list = self.get_file_list()
-        titles = [os.path.split(file)[1] for file in current_list]
+        titles = [file_path.name for file_path in current_list]
         self.application.set_busy_cursor()
         if not initial_load:
             self.main_window.display_progress_bar(len(files))
@@ -410,11 +411,11 @@ class PresentationMediaItem(MediaManagerItem):
         :param show_error: not used
         :return:
         """
-        files = Settings().value(self.settings_section + '/presentations files')
+        file_paths = Settings().value(self.settings_section + '/presentations files')
         results = []
         string = string.lower()
-        for file in files:
-            filename = os.path.split(str(file))[1]
-            if filename.lower().find(string) > -1:
-                results.append([file, filename])
+        for file_path in file_paths:
+            file_name = file_path.name
+            if file_name.lower().find(string) > -1:
+                results.append([path_to_str(file_path), file_name])
         return results
diff --git a/openlp/plugins/presentations/lib/pdfcontroller.py b/openlp/plugins/presentations/lib/pdfcontroller.py
index bd8e48da3..f4a091551 100644
--- a/openlp/plugins/presentations/lib/pdfcontroller.py
+++ b/openlp/plugins/presentations/lib/pdfcontroller.py
@@ -28,7 +28,7 @@ from subprocess import check_output, CalledProcessError
 
 from openlp.core.common import AppLocation, check_binary_exists
 from openlp.core.common import Settings, is_win
-from openlp.core.common.path import Path
+from openlp.core.common.path import Path, path_to_str
 from openlp.core.lib import ScreenList
 from openlp.plugins.presentations.lib.presentationcontroller import PresentationController, PresentationDocument
 
@@ -113,7 +113,7 @@ class PdfController(PresentationController):
         self.also_supports = []
         # Use the user defined program if given
         if Settings().value('presentations/enable_pdf_program'):
-            pdf_program = Settings().value('presentations/pdf_program')
+            pdf_program = path_to_str(Settings().value('presentations/pdf_program'))
             program_type = self.process_check_binary(pdf_program)
             if program_type == 'gs':
                 self.gsbin = pdf_program
diff --git a/openlp/plugins/presentations/lib/presentationtab.py b/openlp/plugins/presentations/lib/presentationtab.py
index fa804f2d3..3e92827c8 100644
--- a/openlp/plugins/presentations/lib/presentationtab.py
+++ b/openlp/plugins/presentations/lib/presentationtab.py
@@ -155,9 +155,7 @@ class PresentationTab(SettingsTab):
         enable_pdf_program = Settings().value(self.settings_section + '/enable_pdf_program')
         self.pdf_program_check_box.setChecked(enable_pdf_program)
         self.program_path_edit.setEnabled(enable_pdf_program)
-        pdf_program = Settings().value(self.settings_section + '/pdf_program')
-        if pdf_program:
-            self.program_path_edit.path = str_to_path(pdf_program)
+        self.program_path_edit.path = Settings().value(self.settings_section + '/pdf_program')
 
     def save(self):
         """
@@ -193,13 +191,13 @@ class PresentationTab(SettingsTab):
             Settings().setValue(setting_key, self.ppt_window_check_box.checkState())
             changed = True
         # Save pdf-settings
-        pdf_program = path_to_str(self.program_path_edit.path)
+        pdf_program_path = self.program_path_edit.path
         enable_pdf_program = self.pdf_program_check_box.checkState()
         # If the given program is blank disable using the program
-        if pdf_program == '':
+        if not pdf_program_path:
             enable_pdf_program = 0
-        if pdf_program != Settings().value(self.settings_section + '/pdf_program'):
-            Settings().setValue(self.settings_section + '/pdf_program', pdf_program)
+        if pdf_program_path != Settings().value(self.settings_section + '/pdf_program'):
+            Settings().setValue(self.settings_section + '/pdf_program', pdf_program_path)
             changed = True
         if enable_pdf_program != Settings().value(self.settings_section + '/enable_pdf_program'):
             Settings().setValue(self.settings_section + '/enable_pdf_program', enable_pdf_program)
diff --git a/openlp/plugins/presentations/presentationplugin.py b/openlp/plugins/presentations/presentationplugin.py
index a91f78794..6f9989565 100644
--- a/openlp/plugins/presentations/presentationplugin.py
+++ b/openlp/plugins/presentations/presentationplugin.py
@@ -39,7 +39,7 @@ log = logging.getLogger(__name__)
 
 __default_settings__ = {'presentations/override app': QtCore.Qt.Unchecked,
                         'presentations/enable_pdf_program': QtCore.Qt.Unchecked,
-                        'presentations/pdf_program': '',
+                        'presentations/pdf_program': None,
                         'presentations/Impress': QtCore.Qt.Checked,
                         'presentations/Powerpoint': QtCore.Qt.Checked,
                         'presentations/Powerpoint Viewer': QtCore.Qt.Checked,
diff --git a/openlp/plugins/songs/forms/songimportform.py b/openlp/plugins/songs/forms/songimportform.py
index e3c0eb620..502d40126 100644
--- a/openlp/plugins/songs/forms/songimportform.py
+++ b/openlp/plugins/songs/forms/songimportform.py
@@ -239,13 +239,11 @@ class SongImportForm(OpenLPWizard, RegistryProperties):
             filters += ';;'
         filters += '{text} (*)'.format(text=UiStrings().AllFiles)
         file_paths, selected_filter = FileDialog.getOpenFileNames(
-            self, title,
-            str_to_path(Settings().value(self.plugin.settings_section + '/last directory import')), filters)
+            self, title, Settings().value(self.plugin.settings_section + '/last directory import'), filters)
         if file_paths:
             file_names = [path_to_str(file_path) for file_path in file_paths]
             listbox.addItems(file_names)
-            Settings().setValue(self.plugin.settings_section + '/last directory import',
-                                os.path.split(str(file_names[0]))[0])
+            Settings().setValue(self.plugin.settings_section + '/last directory import', file_paths[0].parent)
 
     def get_list_of_files(self, list_box):
         """
@@ -363,14 +361,15 @@ class SongImportForm(OpenLPWizard, RegistryProperties):
     def on_error_save_to_button_clicked(self):
         """
         Save the error report to a file.
+
+        :rtype: None
         """
-        filename, filter_used = QtWidgets.QFileDialog.getSaveFileName(
+        file_path, filter_used = FileDialog.getSaveFileName(
             self, Settings().value(self.plugin.settings_section + '/last directory import'))
-        if not filename:
+        if not file_path:
             return
-        report_file = codecs.open(filename, 'w', 'utf-8')
-        report_file.write(self.error_report_text_edit.toPlainText())
-        report_file.close()
+        with file_path.open('w', encoding='utf-8') as report_file:
+            report_file.write(self.error_report_text_edit.toPlainText())
 
     def add_file_select_item(self):
         """
diff --git a/openlp/plugins/songs/songsplugin.py b/openlp/plugins/songs/songsplugin.py
index f156f3ee3..1edb999dc 100644
--- a/openlp/plugins/songs/songsplugin.py
+++ b/openlp/plugins/songs/songsplugin.py
@@ -66,8 +66,8 @@ __default_settings__ = {
     'songs/display songbook': False,
     'songs/display written by': True,
     'songs/display copyright symbol': False,
-    'songs/last directory import': '',
-    'songs/last directory export': '',
+    'songs/last directory import': None,
+    'songs/last directory export': None,
     'songs/songselect username': '',
     'songs/songselect password': '',
     'songs/songselect searches': '',
diff --git a/openlp/plugins/songusage/forms/songusagedetailform.py b/openlp/plugins/songusage/forms/songusagedetailform.py
index b69b04c7a..7aa636635 100644
--- a/openlp/plugins/songusage/forms/songusagedetailform.py
+++ b/openlp/plugins/songusage/forms/songusagedetailform.py
@@ -56,14 +56,16 @@ class SongUsageDetailForm(QtWidgets.QDialog, Ui_SongUsageDetailDialog, RegistryP
         """
         self.from_date_calendar.setSelectedDate(Settings().value(self.plugin.settings_section + '/from date'))
         self.to_date_calendar.setSelectedDate(Settings().value(self.plugin.settings_section + '/to date'))
-        self.report_path_edit.path = str_to_path(
-            Settings().value(self.plugin.settings_section + '/last directory export'))
+        self.report_path_edit.path = Settings().value(self.plugin.settings_section + '/last directory export')
 
     def on_report_path_edit_path_changed(self, file_path):
         """
-        Triggered when the Directory selection button is clicked
+        Called when the path in the `PathEdit` has changed
+
+        :param openlp.core.common.path.Path file_path: The new path.
+        :rtype: None
         """
-        Settings().setValue(self.plugin.settings_section + '/last directory export', path_to_str(file_path))
+        Settings().setValue(self.plugin.settings_section + '/last directory export', file_path)
 
     def accept(self):
         """
diff --git a/openlp/plugins/songusage/songusageplugin.py b/openlp/plugins/songusage/songusageplugin.py
index 705d86f5d..d0c2f7fe7 100644
--- a/openlp/plugins/songusage/songusageplugin.py
+++ b/openlp/plugins/songusage/songusageplugin.py
@@ -50,7 +50,7 @@ __default_settings__ = {
     'songusage/active': False,
     'songusage/to date': QtCore.QDate(YEAR, 8, 31),
     'songusage/from date': QtCore.QDate(YEAR - 1, 9, 1),
-    'songusage/last directory export': ''
+    'songusage/last directory export': None
 }
 
 
diff --git a/tests/functional/openlp_core_common/test_applocation.py b/tests/functional/openlp_core_common/test_applocation.py
index c8fcc151d..7dff1a073 100644
--- a/tests/functional/openlp_core_common/test_applocation.py
+++ b/tests/functional/openlp_core_common/test_applocation.py
@@ -42,12 +42,14 @@ class TestAppLocation(TestCase):
         """
         with patch('openlp.core.common.applocation.Settings') as mocked_class, \
                 patch('openlp.core.common.AppLocation.get_directory') as mocked_get_directory, \
-                patch('openlp.core.common.applocation.check_directory_exists') as mocked_check_directory_exists:
+                patch('openlp.core.common.applocation.check_directory_exists') as mocked_check_directory_exists, \
+                patch('openlp.core.common.applocation.os') as mocked_os:
             # GIVEN: A mocked out Settings class and a mocked out AppLocation.get_directory()
             mocked_settings = mocked_class.return_value
             mocked_settings.contains.return_value = False
-            mocked_get_directory.return_value = Path('test', 'dir')
+            mocked_get_directory.return_value = os.path.join('test', 'dir')
             mocked_check_directory_exists.return_value = True
+            mocked_os.path.normpath.return_value = os.path.join('test', 'dir')
 
             # WHEN: we call AppLocation.get_data_path()
             data_path = AppLocation.get_data_path()
@@ -55,8 +57,8 @@ class TestAppLocation(TestCase):
             # THEN: check that all the correct methods were called, and the result is correct
             mocked_settings.contains.assert_called_with('advanced/data path')
             mocked_get_directory.assert_called_with(AppLocation.DataDir)
-            mocked_check_directory_exists.assert_called_with(Path('test', 'dir'))
-            self.assertEqual(Path('test', 'dir'), data_path, 'Result should be "test/dir"')
+            mocked_check_directory_exists.assert_called_with(os.path.join('test', 'dir'))
+            self.assertEqual(os.path.join('test', 'dir'), data_path, 'Result should be "test/dir"')
 
     def test_get_data_path_with_custom_location(self):
         """
diff --git a/tests/functional/openlp_core_common/test_settings.py b/tests/functional/openlp_core_common/test_settings.py
index 6b30d0218..fe6e68604 100644
--- a/tests/functional/openlp_core_common/test_settings.py
+++ b/tests/functional/openlp_core_common/test_settings.py
@@ -26,7 +26,6 @@ from unittest import TestCase
 from unittest.mock import patch
 
 from openlp.core.common import Settings
-from openlp.core.common.settings import recent_files_conv
 
 from tests.helpers.testmixin import TestMixin
 
@@ -48,25 +47,6 @@ class TestSettings(TestCase, TestMixin):
         """
         self.destroy_settings()
 
-    def test_recent_files_conv(self):
-        """
-        Test that recent_files_conv, converts various possible types of values correctly.
-        """
-        # GIVEN: A list of possible value types and the expected results
-        possible_values = [(['multiple', 'values'], ['multiple', 'values']),
-                           (['single value'], ['single value']),
-                           ('string value', ['string value']),
-                           (b'bytes value', ['bytes value']),
-                           ([], []),
-                           (None, [])]
-
-        # WHEN: Calling recent_files_conv with the possible values
-        for value, expected_result in possible_values:
-            actual_result = recent_files_conv(value)
-
-            # THEN: The actual result should be the same as the expected result
-            self.assertEqual(actual_result, expected_result)
-
     def test_settings_basic(self):
         """
         Test the Settings creation and its default usage
diff --git a/tests/functional/openlp_core_ui/test_exceptionform.py b/tests/functional/openlp_core_ui/test_exceptionform.py
index f205a4ce2..37a040aa6 100644
--- a/tests/functional/openlp_core_ui/test_exceptionform.py
+++ b/tests/functional/openlp_core_ui/test_exceptionform.py
@@ -29,6 +29,7 @@ from unittest import TestCase
 from unittest.mock import mock_open, patch
 
 from openlp.core.common import Registry
+from openlp.core.common.path import Path
 from openlp.core.ui import exceptionform
 
 from tests.helpers.testmixin import TestMixin
@@ -154,7 +155,7 @@ class TestExceptionForm(TestMixin, TestCase):
         # THEN: Verify strings were formatted properly
         mocked_add_query_item.assert_called_with('body', MAIL_ITEM_TEXT)
 
-    @patch("openlp.core.ui.exceptionform.QtWidgets.QFileDialog.getSaveFileName")
+    @patch("openlp.core.ui.exceptionform.FileDialog.getSaveFileName")
     @patch("openlp.core.ui.exceptionform.Qt")
     def test_on_save_report_button_clicked(self,
                                            mocked_qt,
@@ -181,7 +182,7 @@ class TestExceptionForm(TestMixin, TestCase):
         mocked_qt.PYQT_VERSION_STR = 'PyQt5 Test'
         mocked_is_linux.return_value = False
         mocked_application_version.return_value = 'Trunk Test'
-        mocked_save_filename.return_value = ['testfile.txt', ]
+        mocked_save_filename.return_value = (Path('testfile.txt'), 'filter')
 
         test_form = exceptionform.ExceptionForm()
         test_form.file_attachment = None
diff --git a/tests/functional/openlp_plugins/images/test_lib.py b/tests/functional/openlp_plugins/images/test_lib.py
index f00463d67..821a64bb0 100644
--- a/tests/functional/openlp_plugins/images/test_lib.py
+++ b/tests/functional/openlp_plugins/images/test_lib.py
@@ -28,6 +28,7 @@ from unittest.mock import ANY, MagicMock, patch
 from PyQt5 import QtCore, QtWidgets
 
 from openlp.core.common import Registry
+from openlp.core.common.path import Path
 from openlp.plugins.images.lib.db import ImageFilenames, ImageGroups
 from openlp.plugins.images.lib.mediaitem import ImageMediaItem
 
@@ -65,7 +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, '/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')
@@ -82,7 +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, '/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):
diff --git a/tests/functional/openlp_plugins/media/test_mediaitem.py b/tests/functional/openlp_plugins/media/test_mediaitem.py
index 80d21da91..d0ed7499f 100644
--- a/tests/functional/openlp_plugins/media/test_mediaitem.py
+++ b/tests/functional/openlp_plugins/media/test_mediaitem.py
@@ -28,6 +28,7 @@ from unittest.mock import MagicMock, patch
 from PyQt5 import QtCore
 
 from openlp.core import Settings
+from openlp.core.common.path import Path
 from openlp.plugins.media.lib.mediaitem import MediaMediaItem
 
 from tests.helpers.testmixin import TestMixin
@@ -66,7 +67,7 @@ class MediaItemTest(TestCase, TestMixin):
         Media Remote Search Successful find
         """
         # GIVEN: The Mediaitem set up a list of media
-        Settings().setValue(self.media_item.settings_section + '/media files', ['test.mp3', 'test.mp4'])
+        Settings().setValue(self.media_item.settings_section + '/media files', [Path('test.mp3'), Path('test.mp4')])
         # WHEN: Retrieving the test file
         result = self.media_item.search('test.mp4', False)
         # THEN: a file should be found
@@ -77,7 +78,7 @@ class MediaItemTest(TestCase, TestMixin):
         Media Remote Search not find
         """
         # GIVEN: The Mediaitem set up a list of media
-        Settings().setValue(self.media_item.settings_section + '/media files', ['test.mp3', 'test.mp4'])
+        Settings().setValue(self.media_item.settings_section + '/media files', [Path('test.mp3'), Path('test.mp4')])
         # WHEN: Retrieving the test file
         result = self.media_item.search('test.mpx', False)
         # THEN: a file should be found
diff --git a/tests/interfaces/openlp_core_lib/test_pluginmanager.py b/tests/interfaces/openlp_core_lib/test_pluginmanager.py
index 39e964143..2e9e8342f 100644
--- a/tests/interfaces/openlp_core_lib/test_pluginmanager.py
+++ b/tests/interfaces/openlp_core_lib/test_pluginmanager.py
@@ -32,6 +32,7 @@ from unittest.mock import MagicMock, patch
 from PyQt5 import QtWidgets
 
 from openlp.core.common import Registry, Settings
+from openlp.core.common.path import Path
 from openlp.core.lib.pluginmanager import PluginManager
 
 from tests.helpers.testmixin import TestMixin
@@ -48,7 +49,7 @@ class TestPluginManager(TestCase, TestMixin):
         """
         self.setup_application()
         self.build_settings()
-        self.temp_dir = mkdtemp('openlp')
+        self.temp_dir = Path(mkdtemp('openlp'))
         Settings().setValue('advanced/data path', self.temp_dir)
         Registry.create()
         Registry().register('service_list', MagicMock())
@@ -62,7 +63,7 @@ class TestPluginManager(TestCase, TestMixin):
         # On windows we need to manually garbage collect to close sqlalchemy files
         # to avoid errors when temporary files are deleted.
         gc.collect()
-        shutil.rmtree(self.temp_dir)
+        shutil.rmtree(str(self.temp_dir))
 
     @patch('openlp.plugins.songusage.lib.db.init_schema')
     @patch('openlp.plugins.songs.lib.db.init_schema')