diff --git a/main.py b/main.py
index 1331aaf..9884b0e 100644
--- a/main.py
+++ b/main.py
@@ -159,10 +159,27 @@ def main():
         log_level,
     )
 
-    if not snapcast_settings.should_ignore_popup() or os.path.exists(snapcast_settings.read_setting("Snapclient/Custom_Path")) is False:
-        dialog = PathInputDialog("snapclient", log_level)
-        if dialog.exec() == QDialog.Accepted:
-            snapcast_settings.set_ignore_popup(dialog.ignore_popup_checkbox.isChecked())
+    def is_executable(file_path):
+        return os.path.isfile(file_path) and os.access(file_path, os.X_OK)
+
+    snapclient_path = snapcast_settings.read_setting("Snapclient/Custom_Path")
+    snapserver_path = snapcast_settings.read_setting("Snapserver/Custom_Path")
+
+    if not snapcast_settings.read_setting("Snapclient/Ignore_Popup"):
+        if not is_executable(snapclient_path):
+            dialog = PathInputDialog("snapclient", log_level)
+            if dialog.exec() == QDialog.Accepted:
+                snapcast_settings.set_ignore_popup(dialog.ignore_popup_checkbox.isChecked())
+                new_path = dialog.get_path()
+                snapcast_settings.write_setting("Snapclient/Custom_Path", new_path)
+
+    if not snapcast_settings.read_setting("Snapserver/Ignore_Popup"):
+        if not is_executable(snapserver_path):
+            dialog = PathInputDialog("snapserver", log_level)
+            if dialog.exec() == QDialog.Accepted:
+                snapcast_settings.set_ignore_popup(dialog.ignore_popup_checkbox.isChecked())
+                new_path = dialog.get_path()
+                snapcast_settings.write_setting("Snapserver/Custom_Path", new_path)
 
     combined_window.show()
     sys.exit(app.exec())
diff --git a/snapcast_gui/fileactions/snapcast_settings.py b/snapcast_gui/fileactions/snapcast_settings.py
index d58154c..c3292d9 100644
--- a/snapcast_gui/fileactions/snapcast_settings.py
+++ b/snapcast_gui/fileactions/snapcast_settings.py
@@ -38,6 +38,7 @@ def ensure_settings(self) -> None:
             "Snapserver/autostart": False,
             "Snapserver/Config_Before_Start": "",
             "Snapserver/Config_After_Start": "",
+            "Snapserver/Ignore_Popup": True,
             "Shortcuts/Open_Settings": "Ctrl+O",
             "Shortcuts/Connect_Disconnect": "Ctrl+C",
             "Shortcuts/Toggle_Snapclient": "Ctrl+E",
@@ -174,21 +175,3 @@ def remove_ip(self, ip: str) -> None:
         self.logger.debug(
             "IP Address {} removed from config file.".format(ip)
         )
-
-    def should_ignore_popup(self) -> bool:
-        """
-        Reads the setting for ignoring the popup and returns its value.
-
-        Returns:
-            bool: True if the popup should be ignored, False otherwise.
-        """
-        return self.read_setting("Snapclient/Ignore_Popup")
-
-    def set_ignore_popup(self, value: bool) -> None:
-        """
-        Updates the setting for ignoring the popup.
-
-        Args:
-            value (bool): The new value for the setting.
-        """
-        self.update_setting("Snapclient/Ignore_Popup", str(value))