diff --git a/src/main/java/name/nathanmcrae/numbersstation/MainController.java b/src/main/java/name/nathanmcrae/numbersstation/MainController.java
index 2fe9beb..f5c6b2d 100644
--- a/src/main/java/name/nathanmcrae/numbersstation/MainController.java
+++ b/src/main/java/name/nathanmcrae/numbersstation/MainController.java
@@ -185,18 +185,24 @@ public class MainController implements Initializable {
 
         Result<MainSettings, Exception> result = MainSettings.load();
         if (!result.hasSuccess()) {
-            // TODO: on failure, prompt user to re-initialize settings
-            Alert alert = new Alert(Alert.AlertType.ERROR);
+            Alert alert = new Alert(Alert.AlertType.ERROR, "Unable to load settings file. See log for details. Reinitialize settings? This may overwrite existing settings.", ButtonType.YES, ButtonType.NO);
             alert.setTitle("Settings load error");
             alert.setHeaderText(null);
-            alert.setContentText("Unable to load settings file");
-            alert.showAndWait();
+            Optional<ButtonType> promptResult = alert.showAndWait();
 
-            return;
+            if (!promptResult.isPresent()) {
+                System.exit(1);
+            }
+
+            if (promptResult.get() == ButtonType.NO) {
+                System.exit(1);
+            }
+
+            settings = new MainSettings();
+        } else {
+            settings = result.getSuccess().get();
         }
 
-        settings = result.getSuccess().get();
-
         selectedStationName.set(settings.getSelectedStationName());
 
         if (selectedStationName.get() == null || selectedStationName.get() == "") {