diff --git a/awx/settings/__init__.py b/awx/settings/__init__.py
index 5883ac92f814..0b2739bde1a4 100644
--- a/awx/settings/__init__.py
+++ b/awx/settings/__init__.py
@@ -5,6 +5,7 @@
     factory,
     export,
     load_envvars,
+    load_python_file_with__injected_context,
     load_standard_settings_files,
     validate,
 )
@@ -46,8 +47,12 @@
 settings_dir = os.environ.get('AWX_SETTINGS_DIR', '/etc/tower/conf.d/')
 settings_files_path = os.path.join(settings_dir, '*.py')
 settings_file_path = os.environ.get('AWX_SETTINGS_FILE', '/etc/tower/settings.py')
-DYNACONF.load_file(settings_file_path)
-DYNACONF.load_file(settings_files_path)
+
+# The following should have been loaded using `DYNACONF.load_file` but we are
+# using `load_python_file_with__injected_context` to maintain backwards compatibility
+load_python_file_with__injected_context(settings_files_path, settings=DYNACONF)
+load_python_file_with__injected_context(settings_file_path, settings=DYNACONF)
+
 
 # Load new standard settings files from
 #  /etc/ansible-automation-platform/ and /etc/ansible-automation-platform/awx/
@@ -56,9 +61,9 @@
 
 # Load optional development only settings
 if DYNACONF.get_environ("AWX_KUBE_DEVEL"):
-    DYNACONF.load_file("kube_defaults.py")
+    load_python_file_with__injected_context("kube_defaults.py", settings=DYNACONF)
 else:
-    DYNACONF.load_file("local_*.py")
+    load_python_file_with__injected_context("local_*.py", settings=DYNACONF)
 
 # Check at least one required setting file has been loaded
 if "production" in DYNACONF.current_env.lower():  # pragma: no cover