diff --git a/Build-Binary.command b/Build-Binary.command
index e1c886f6b..94b5da9ea 100755
--- a/Build-Binary.command
+++ b/Build-Binary.command
@@ -48,7 +48,7 @@ class CreateBinary:
         """
 
         os.chdir(Path(__file__).resolve().parent)
-        print(f"Current Working Directory: \n\t{os.getcwd()}")
+        print(f"Current Working Directory:\n- {os.getcwd()}")
 
 
     def _parse_arguments(self):
diff --git a/resources/logging_handler.py b/resources/logging_handler.py
index 242f70d20..88bed6e20 100644
--- a/resources/logging_handler.py
+++ b/resources/logging_handler.py
@@ -213,6 +213,7 @@ class InitializeLoggingSupport:
             self._display_debug_properties()
 
             if self.constants.cli_mode is True:
+                threading.Thread(target=analytics_handler.Analytics(self.constants).send_crash_report, args=(self.log_filepath,)).start()
                 return
 
             error_msg = f"OpenCore Legacy Patcher encountered the following internal error:\n\n"
diff --git a/resources/wx_gui/gui_entry.py b/resources/wx_gui/gui_entry.py
index c2bcda0ff..f7d2764cf 100644
--- a/resources/wx_gui/gui_entry.py
+++ b/resources/wx_gui/gui_entry.py
@@ -52,6 +52,10 @@ class EntryPoint:
             patches = sys_patch_detect.DetectRootPatch(self.constants.computer.real_model, self.constants).detect_patch_set()
 
         logging.info(f"Entry point set: {entry.__name__}")
+
+        # Normally set by main.py, but transitions from CLI mode may not have this set
+        self.constants.gui_mode = True
+
         self.frame: wx.Frame = entry(
             None,
             title=f"{self.constants.patcher_name} ({self.constants.patcher_version})",
diff --git a/resources/wx_gui/gui_update.py b/resources/wx_gui/gui_update.py
index b3e862ef0..43ddfcc3f 100644
--- a/resources/wx_gui/gui_update.py
+++ b/resources/wx_gui/gui_update.py
@@ -52,6 +52,9 @@ class UpdateFrame(wx.Frame):
                     version_label = dict[key]["Version"]
                     url = dict[key]["Link"]
                     break
+            else:
+                wx.MessageBox("Failed to get update info", "Critical Error")
+                sys.exit(1)
 
         self.version_label = version_label
         self.url = url