diff --git a/.github/workflows/scripts/install.sh b/.github/workflows/scripts/install.sh
index e4eb4748c..f827e5ec5 100755
--- a/.github/workflows/scripts/install.sh
+++ b/.github/workflows/scripts/install.sh
@@ -95,7 +95,7 @@ if [ "$TEST" = "s3" ]; then
   sed -i -e '$a s3_test: true\
 minio_access_key: "'$MINIO_ACCESS_KEY'"\
 minio_secret_key: "'$MINIO_SECRET_KEY'"\
-pulp_scenario_settings: {"MEDIA_ROOT": "", "STORAGES": {"default": {"BACKEND": "storages.backends.s3boto3.S3Boto3Storage", "OPTIONS": {"access_key": "AKIAIT2Z5TDYPX3ARJBA", "addressing_style": "path", "bucket_name": "pulp3", "default_acl": "@none", "endpoint_url": "http://minio:9000", "region_name": "eu-central-1", "secret_key": "fqRvjWaPU5o0fCqQuUWbj9Fainj2pVZtBCiDiieS", "signature_version": "s3v4"}}, "staticfiles": {"BACKEND": "django.contrib.staticfiles.storage.StaticFilesStorage"}}, "domain_enabled": true, "flatpak_index": false, "token_auth_disabled": true}\
+pulp_scenario_settings: {"MEDIA_ROOT": "", "STORAGES": {"default": {"BACKEND": "storages.backends.s3boto3.S3Boto3Storage", "OPTIONS": {"access_key": "AKIAIT2Z5TDYPX3ARJBA", "addressing_style": "path", "bucket_name": "pulp3", "default_acl": "@none", "endpoint_url": "http://minio:9000", "region_name": "eu-central-1", "secret_key": "fqRvjWaPU5o0fCqQuUWbj9Fainj2pVZtBCiDiieS", "signature_version": "s3v4"}}, "staticfiles": {"BACKEND": "django.contrib.staticfiles.storage.StaticFilesStorage"}}, "domain_enabled": true, "enabled_plugins": ["pulp_file", "pulp_container"], "flatpak_index": false, "token_auth_disabled": true}\
 pulp_scenario_env: {}\
 ' vars/main.yaml
   export PULP_API_ROOT="/rerouted/djnd/"
diff --git a/CHANGES/2044.bugfix b/CHANGES/2044.bugfix
new file mode 100644
index 000000000..fbcf33281
--- /dev/null
+++ b/CHANGES/2044.bugfix
@@ -0,0 +1 @@
+Added a deployment check to produce a better error message when pulp_file missing from `ENABLED_PLUGINS`.
diff --git a/pulp_container/app/dynaconf_hooks.py b/pulp_container/app/dynaconf_hooks.py
new file mode 100644
index 000000000..a0560cfcc
--- /dev/null
+++ b/pulp_container/app/dynaconf_hooks.py
@@ -0,0 +1,9 @@
+from dynaconf import ValidationError
+
+
+def post(settings):
+    data = {"dynaconf_merge": True}
+    enabled_plugins = settings.get("ENABLED_PLUGINS")
+    if enabled_plugins and "pulp_file" not in enabled_plugins:
+        raise ValidationError("pulp_file must be enabled to use pulp_container")
+    return data
diff --git a/template_config.yml b/template_config.yml
index a556b3394..3bc717418 100644
--- a/template_config.yml
+++ b/template_config.yml
@@ -89,6 +89,9 @@ pulp_settings_s3:
     staticfiles:
       BACKEND: django.contrib.staticfiles.storage.StaticFilesStorage
   domain_enabled: true
+  enabled_plugins:
+  - pulp_file
+  - pulp_container
   flatpak_index: false
   token_auth_disabled: true
 pydocstyle: true