diff --git a/CLI.py b/CLI.py
index 5087eabf..4cd17834 100644
--- a/CLI.py
+++ b/CLI.py
@@ -355,7 +355,7 @@ def parse_settings():
         },
         "randomSprite": False,
         "outputpath": os.path.join("."),
-        "saveonexit": "ask",
+        "settingsonload": "saved",
         "outputname": "",
         "startinventoryarray": {},
         "notes": ""
@@ -367,6 +367,12 @@ def parse_settings():
     # read saved settings file if it exists and set these
     settings_path = os.path.join(".", "resources", "user", "settings.json")
     settings = apply_settings_file(settings, settings_path)
+    if settings["settingsonload"] == "saved":
+        settings_path = os.path.join(".", "resources", "user", "saved.json")
+        settings = apply_settings_file(settings, settings_path)
+    elif settings["settingsonload"] == "lastused":
+        settings_path = os.path.join(".", "resources", "user", "last.json")
+        settings = apply_settings_file(settings, settings_path)
     return settings
 
 # Priority fallback is:
diff --git a/Gui.py b/Gui.py
index a0f4726f..4aecfa03 100755
--- a/Gui.py
+++ b/Gui.py
@@ -37,19 +37,31 @@ def check_python_version(fish):
         messagebox.showinfo("Door Shuffle " + ESVersion, fish.translate("cli","cli","old.python.version") % sys.version)
 
 
-def guiMain(args=None):
-    # Save settings to file
-    def save_settings(args):
-        user_resources_path = os.path.join(".", "resources", "user")
-        settings_path = os.path.join(user_resources_path)
-        if not os.path.exists(settings_path):
-            os.makedirs(settings_path)
-        for widget in self.pages["adjust"].content.widgets:
-            args["adjust." + widget] = self.pages["adjust"].content.widgets[widget].storageVar.get()
-        with open(os.path.join(settings_path, "settings.json"), "w+") as f:
-            f.write(json.dumps(args, indent=2))
-        os.chmod(os.path.join(settings_path, "settings.json"),0o755)
+# Save settings to file
+def save_settings(gui, args, filename):
+    user_resources_path = os.path.join(".", "resources", "user")
+    settings_path = os.path.join(user_resources_path)
+    if not os.path.exists(settings_path):
+        os.makedirs(settings_path)
+    output_args = {}
+    settings = ["create_rom", "suppress_rom", "bps", "create_spoiler", "suppress_spoiler",
+                "calc_playthrough", "skip_playthrough", "print_custom_yaml", "settingsonload",
+                "rom", "enemizercli", "outputpath"]
+    if filename == "settings.json":
+        for s in settings:
+            output_args[s] = args[s]
+        for widget in gui.pages["adjust"].content.widgets:
+            output_args["adjust." + widget] = gui.pages["adjust"].content.widgets[widget].storageVar.get()
+    else:
+        for k, v in args.items():
+            if k not in settings and not k.startswith("adjust."):
+                output_args[k] = v
+    with open(os.path.join(settings_path, filename), "w+") as f:
+        f.write(json.dumps(output_args, indent=2))
+    os.chmod(os.path.join(settings_path, filename),0o755)
 
+    
+def guiMain(args=None):
     # Save settings from GUI
     def save_settings_from_gui(confirm):
         gui_args = vars(create_guiargs(self))
@@ -57,23 +69,14 @@ def guiMain(args=None):
             gui_args['sprite'] = 'random'
         elif gui_args['sprite']:
             gui_args['sprite'] = gui_args['sprite'].name
-        save_settings(gui_args)
+        save_settings(self, gui_args, "saved.json")
+        save_settings(self, gui_args, "settings.json")
         if confirm:
             messagebox.showinfo("Overworld Shuffle " + ORVersion, "Settings saved from GUI.")
 
     # routine for exiting the app
     def guiExit():
-        skip_exit = False
-        if self.settings['saveonexit'] == 'ask':
-            dosave = messagebox.askyesnocancel("Overworld Shuffle " + ORVersion, "Save settings before exit?")
-            if dosave:
-                save_settings_from_gui(True)
-            if dosave is None:
-                skip_exit = True
-        elif self.settings['saveonexit'] == 'always':
-            save_settings_from_gui(False)
-        if not skip_exit:
-            sys.exit(0)
+        sys.exit(0)
 
     # make main window
     # add program title & version number
diff --git a/resources/app/cli/args.json b/resources/app/cli/args.json
index 8c21e15a..e723ee76 100644
--- a/resources/app/cli/args.json
+++ b/resources/app/cli/args.json
@@ -575,11 +575,11 @@
     "action": "store_true",
     "type": "bool"
   },
-  "saveonexit": {
+  "settingsonload": {
     "choices": [
-      "ask",
-      "always",
-      "never"
+      "default",
+      "saved",
+      "lastused"
     ]
   },
   "outputname": {},
diff --git a/resources/app/gui/lang/en.json b/resources/app/gui/lang/en.json
index 36ffe2fb..0ae493d2 100644
--- a/resources/app/gui/lang/en.json
+++ b/resources/app/gui/lang/en.json
@@ -236,10 +236,10 @@
     "randomizer.generation.calcplaythrough": "Calculate Playthrough",
     "randomizer.generation.print_custom_yaml": "Print Customizer File",
 
-    "randomizer.generation.saveonexit": "Save Settings on Exit",
-    "randomizer.generation.saveonexit.ask": "Ask Me",
-    "randomizer.generation.saveonexit.always": "Always",
-    "randomizer.generation.saveonexit.never": "Never",
+    "randomizer.generation.settingsonload": "Settings On Load",
+    "randomizer.generation.settingsonload.default": "Default",
+    "randomizer.generation.settingsonload.saved": "Saved",
+    "randomizer.generation.settingsonload.lastused": "Last Used",
 
     "randomizer.generation.rom": "Base Rom: ",
     "randomizer.generation.rom.button": "Select Rom",
diff --git a/resources/app/gui/randomize/generation/widgets.json b/resources/app/gui/randomize/generation/widgets.json
index 22f9decc..a410f227 100644
--- a/resources/app/gui/randomize/generation/widgets.json
+++ b/resources/app/gui/randomize/generation/widgets.json
@@ -1,11 +1,11 @@
 {
   "widgets": {
-    "saveonexit": {
+    "settingsonload": {
       "type": "selectbox",
       "options": [
-        "ask",
-        "always",
-        "never"
+        "default",
+        "saved",
+        "lastused"
       ]
     }
   }
diff --git a/source/classes/constants.py b/source/classes/constants.py
index e3fbf1b1..c8e15532 100644
--- a/source/classes/constants.py
+++ b/source/classes/constants.py
@@ -148,7 +148,7 @@ SETTINGSTOPROCESS = {
       "createrom": "create_rom",
       "calcplaythrough": "calc_playthrough",
       "print_custom_yaml": "print_custom_yaml",
-      "saveonexit": "saveonexit"
+      "settingsonload": "settingsonload"
     }
   },
   "startinventory": {
diff --git a/source/gui/bottom.py b/source/gui/bottom.py
index c53842d7..3d37908e 100644
--- a/source/gui/bottom.py
+++ b/source/gui/bottom.py
@@ -68,6 +68,15 @@ def bottom_frame(self, parent, args=None):
     self.widgets[key].pack(side=LEFT)
 
     def generateRom():
+        guiargs = create_guiargs(parent)
+        argsDump = vars(guiargs)
+        from Gui import save_settings
+        if parent.randomSprite.get():
+            argsDump['sprite'] = 'random'
+        elif argsDump['sprite']:
+            argsDump['sprite'] = argsDump['sprite'].name
+        save_settings(parent, argsDump, "last.json")
+
         guiargs = create_guiargs(parent)
         # get default values for missing parameters
         for k,v in vars(parse_cli(['--multi', str(guiargs.multi)])).items():