diff --git a/ardupilot_methodic_configurator/frontend_tkinter_progress_window.py b/ardupilot_methodic_configurator/frontend_tkinter_progress_window.py
index 8dbbf2015..98db42057 100644
--- a/ardupilot_methodic_configurator/frontend_tkinter_progress_window.py
+++ b/ardupilot_methodic_configurator/frontend_tkinter_progress_window.py
@@ -18,7 +18,7 @@
 from ardupilot_methodic_configurator.frontend_tkinter_base_window import BaseWindow
 
 
-class ProgressWindow:
+class ProgressWindow:  # pylint: disable=too-many-instance-attributes
     """
     A class for creating and managing a progress window in the application.
 
@@ -42,6 +42,7 @@ def __init__(  # pylint: disable=too-many-arguments, too-many-positional-argumen
         self.progress_window = tk.Toplevel(self.parent)
         # Withdraw immediately to prevent flicker while setting up
         self.progress_window.withdraw()
+        self._is_aqua = self.progress_window.tk.call("tk", "windowingsystem") == "aqua"
         self.progress_window.title(title)
         try:
             dpi = self.progress_window.winfo_fpixels("1i")
@@ -117,9 +118,12 @@ def update_progress_bar(self, current_value: int, max_value: int) -> None:
                 return
 
             if self.only_show_when_update_progress_called and not self._shown:
+                self.progress_window.update_idletasks()  # Calculate widgets first
                 self.progress_window.deiconify()
                 self._center_progress_window()
                 self.progress_window.lift()
+                if getattr(self, "_is_aqua", False):
+                    self.progress_window.update()  # macOS needs this to paint pixels NOW
                 self._shown = True
             elif not self.only_show_when_update_progress_called:
                 self.progress_window.lift()
@@ -143,6 +147,9 @@ def update_progress_bar(self, current_value: int, max_value: int) -> None:
                 # other windows while a blocking upload/download is in flight.
                 self.progress_bar.update_idletasks()
 
+                if getattr(self, "_is_aqua", False):
+                    self.progress_window.update()
+
                 # Close the progress window when the process is complete
                 if current_value == max_value:
                     self.progress_window.destroy()
diff --git a/ardupilot_methodic_configurator/frontend_tkinter_show.py b/ardupilot_methodic_configurator/frontend_tkinter_show.py
index 95bca5d93..443cc03eb 100644
--- a/ardupilot_methodic_configurator/frontend_tkinter_show.py
+++ b/ardupilot_methodic_configurator/frontend_tkinter_show.py
@@ -481,9 +481,11 @@ def __init__(  # pylint: disable=too-many-arguments, too-many-positional-argumen
         if tag_name and isinstance(self.widget, tk.Text):
             self.widget.tag_bind(tag_name, "<Enter>", self.schedule_show, "+")
             self.widget.tag_bind(tag_name, "<Leave>", self.destroy_hide, "+")
+            self.widget.tag_bind(tag_name, "<ButtonPress>", self.destroy_hide, "+")
         else:
             self.widget.bind("<Enter>", self.schedule_show, "+")
             self.widget.bind("<Leave>", self.destroy_hide, "+")
+            self.widget.bind("<ButtonPress>", self.destroy_hide, "+")
 
         self.widget.bind("<Destroy>", self._on_widget_destroy, "+")
 
@@ -497,15 +499,11 @@ def _cancel_timer(self, name: str) -> None:
     def _cancel_show(self) -> None:
         self._cancel_timer("show")
 
-    def _on_widget_destroy(self, event: Optional[tk.Event] = None) -> None:  # noqa: ARG002 # pylint: disable=unused-argument
+    def _on_widget_destroy(self, event: Optional[tk.Event] = None) -> None:
         """Stop any active timers if the widget is destroyed."""
-        self._cancel_show()
-        self._cancel_timer("alpha")
-
-        if self.tooltip:
-            with contextlib.suppress(tk.TclError):
-                self.tooltip.destroy()
-            self.tooltip = None
+        if event and getattr(event, "widget", None) is not self.widget:
+            return
+        self.force_hide()
 
     def _hide_active_tooltip(self) -> None:
         """Hide another active tooltip before showing this one."""
@@ -539,8 +537,12 @@ def create_show(self, _event: Optional[tk.Event] = None) -> None:
             return  # Avoid redundant tooltip creation
 
         self.tooltip = cast("tk.Toplevel", self.toplevel_class(self.widget, bg="#ffffe0"))
+
+        # Remove the window buttons on all OSs
         self.tooltip.wm_overrideredirect(True)  # noqa: FBT003
-        self.tooltip.withdraw()
+
+        if not self._is_aqua:
+            self.tooltip.withdraw()
 
         if self._is_aqua:
             self.tooltip.attributes("-alpha", 0.0)