diff --git a/hyperglass/configuration/__init__.py b/hyperglass/configuration/__init__.py
index 886726a..8ee7825 100644
--- a/hyperglass/configuration/__init__.py
+++ b/hyperglass/configuration/__init__.py
@@ -5,7 +5,13 @@ from hyperglass.state import use_state
 from hyperglass.defaults.directives import init_builtin_directives
 
 # Local
-from .validate import init_params, init_devices, init_ui_params, init_directives
+from .validate import (
+    init_files,
+    init_params,
+    init_devices,
+    init_ui_params,
+    init_directives,
+)
 
 __all__ = ("init_user_config",)
 
@@ -13,6 +19,7 @@ __all__ = ("init_user_config",)
 def init_user_config() -> None:
     """Initialize all user configurations and add them to global state."""
     state = use_state()
+    init_files()
 
     params = init_params()
     builtins = init_builtin_directives()
diff --git a/hyperglass/configuration/validate.py b/hyperglass/configuration/validate.py
index 5379283..0f40568 100644
--- a/hyperglass/configuration/validate.py
+++ b/hyperglass/configuration/validate.py
@@ -1,6 +1,5 @@
 """Import configuration files and run validation."""
 
-
 # Third Party
 from pydantic import ValidationError
 
@@ -18,13 +17,23 @@ from .load import load_config
 from .markdown import get_markdown
 
 __all__ = (
-    "init_params",
-    "init_directives",
     "init_devices",
+    "init_directives",
+    "init_files",
+    "init_params",
     "init_ui_params",
 )
 
 
+def init_files() -> None:
+    """Check if required directories exist and if not, create them."""
+    for directory in ("plugins", "static/images"):
+        path = Settings.app_path / directory
+        if not path.exists():
+            path.mkdir(parents=True)
+            log.debug("Created directory {!s}", path)
+
+
 def init_params() -> "Params":
     """Validate & initialize configuration parameters."""
     user_config = load_config("config", required=False)