diff --git a/kolibri/utils/cli.py b/kolibri/utils/cli.py
index 149e71dcd45..ee3283fe6ba 100644
--- a/kolibri/utils/cli.py
+++ b/kolibri/utils/cli.py
@@ -2,7 +2,7 @@
 import signal
 import sys
 import traceback
-from pkgutil import find_loader
+from contextlib import contextmanager
 
 import click
 from django.core.management import execute_from_command_line
@@ -19,32 +19,35 @@
 from kolibri.plugins.utils import enable_plugin
 from kolibri.plugins.utils import iterate_plugins
 from kolibri.utils import server
+from kolibri.utils.compat import module_exists
 from kolibri.utils.conf import OPTIONS
 from kolibri.utils.debian_check import check_debian_user
 from kolibri.utils.main import initialize
+from kolibri.utils.main import set_django_settings_and_python_path
 from kolibri.utils.main import setup_logging
 
 
 logger = logging.getLogger(__name__)
 
 
-# We use Unicode strings for Python 2.7 throughout the codebase, so choosing
-# to silence these warnings.
-# Ref:
-# https://github.com/learningequality/kolibri/pull/5494#discussion_r318057385
-# https://github.com/PythonCharmers/python-future/issues/22
-click.disable_unicode_literals_warning = True
+@contextmanager
+def _patch_python_path(pythonpath):
+    if pythonpath:
+        sys.path.insert(0, pythonpath)
+    try:
+        yield
+    finally:
+        if pythonpath:
+            sys.path.remove(pythonpath)
 
 
 def validate_module(ctx, param, value):
     if value:
-        try:
-            if not find_loader(value):
-                raise ImportError
-        except ImportError:
-            raise click.BadParameter(
-                "{param} must be a valid python module import path"
-            )
+        with _patch_python_path(ctx.params.get("pythonpath")):
+            if not module_exists(value):
+                raise click.BadParameter(
+                    "{param} must be a valid python module import path"
+                )
     return value
 
 
@@ -72,8 +75,11 @@ def validate_module(ctx, param, value):
 
 pythonpath_option = click.Option(
     param_decls=["--pythonpath"],
-    type=click.Path(exists=True, file_okay=False),
+    type=click.Path(exists=True, file_okay=False, resolve_path=True),
     help="Add a path to the Python path",
+    # Set this to is_eager to ensure the option is set
+    # before we attempt to import the settings module
+    is_eager=True,
 )
 
 skip_update_option = click.Option(
@@ -91,11 +97,10 @@ def validate_module(ctx, param, value):
 )
 
 
-base_params = [debug_option, debug_database_option, noinput_option]
+base_params = [debug_option, debug_database_option, noinput_option, pythonpath_option]
 
 initialize_params = base_params + [
     settings_option,
-    pythonpath_option,
     skip_update_option,
 ]
 
@@ -135,6 +140,8 @@ def invoke(self, ctx):
             debug=ctx.params.get("debug"),
             debug_database=ctx.params.get("debug_database"),
         )
+        # We want to allow overriding the Python path for commands that don't require Django
+        set_django_settings_and_python_path(None, ctx.params.get("pythonpath"))
         for param in base_params:
             ctx.params.pop(param.name)
         return super(KolibriCommand, self).invoke(ctx)
@@ -163,6 +170,8 @@ def invoke(self, ctx):
             debug=ctx.params.get("debug"),
             debug_database=ctx.params.get("debug_database"),
         )
+        # We want to allow overriding the Python path for commands that don't require Django
+        set_django_settings_and_python_path(None, ctx.params.get("pythonpath"))
         for param in base_params:
             ctx.params.pop(param.name)
         return super(KolibriGroupCommand, self).invoke(ctx)
diff --git a/kolibri/utils/main.py b/kolibri/utils/main.py
index 19509d1ff5a..d050b5d3343 100644
--- a/kolibri/utils/main.py
+++ b/kolibri/utils/main.py
@@ -9,7 +9,6 @@
 from django.conf import settings
 from django.core.exceptions import ValidationError
 from django.core.management import call_command
-from django.core.management.base import handle_default_options
 from django.db.utils import DatabaseError
 
 import kolibri
@@ -112,14 +111,6 @@ def _migrate_databases():
     call_command("loaddata", "scopedefinitions")
 
 
-class DefaultDjangoOptions(object):
-    __slots__ = ["settings", "pythonpath"]
-
-    def __init__(self, settings, pythonpath):
-        self.settings = settings
-        self.pythonpath = pythonpath
-
-
 def setup_logging(debug=False, debug_database=False):
     """
     Configures logging in cases where a Django environment is not supposed
@@ -291,6 +282,15 @@ def _upgrades_after_django_setup(updated, version):
             logging.error(e)
 
 
+def set_django_settings_and_python_path(django_settings, pythonpath):
+
+    if django_settings:
+        os.environ["DJANGO_SETTINGS_MODULE"] = django_settings
+
+    if pythonpath and pythonpath not in sys.path:
+        sys.path.insert(0, pythonpath)
+
+
 def initialize(  # noqa C901
     skip_update=False,
     settings=None,
@@ -307,9 +307,7 @@ def initialize(  # noqa C901
 
     setup_logging(debug=debug, debug_database=debug_database)
 
-    default_options = DefaultDjangoOptions(settings, pythonpath)
-
-    handle_default_options(default_options)
+    set_django_settings_and_python_path(settings, pythonpath)
 
     version = get_version()