diff --git a/gui/builtinContextMenus/skillAffectors.py b/gui/builtinContextMenus/skillAffectors.py
index 4dc254f13..c11072ccc 100644
--- a/gui/builtinContextMenus/skillAffectors.py
+++ b/gui/builtinContextMenus/skillAffectors.py
@@ -89,6 +89,9 @@ class ChangeAffectingSkills(ContextMenuSingle):
         self.skillIds = {}
         sub = wx.Menu()
 
+        # When rootMenu is None (direct menu access), use sub for binding on Windows
+        bindMenu = rootMenu if (rootMenu is not None and msw) else (sub if msw else None)
+
         # Add "All" entry
         allItem = wx.MenuItem(sub, ContextMenuSingle.nextID(), _t("All"))
         grandSubAll = wx.Menu()
@@ -99,7 +102,7 @@ class ChangeAffectingSkills(ContextMenuSingle):
             id = ContextMenuSingle.nextID()
             self.skillIds[id] = (None, i, False)  # None indicates "All" was selected, False = not "up"
             label = _t("Level %s") % i
-            menuItem = wx.MenuItem(rootMenu if msw else grandSubAll, id, label, kind=wx.ITEM_RADIO)
+            menuItem = wx.MenuItem(bindMenu if bindMenu else grandSubAll, id, label, kind=wx.ITEM_RADIO)
             grandSubAll.Bind(wx.EVT_MENU, self.handleSkillChange, menuItem)
             grandSubAll.Append(menuItem)
 
@@ -111,7 +114,7 @@ class ChangeAffectingSkills(ContextMenuSingle):
             id = ContextMenuSingle.nextID()
             self.skillIds[id] = (None, i, True)  # None indicates "All" was selected, True = "up" only
             label = _t("Up Level %s") % i
-            menuItem = wx.MenuItem(rootMenu if msw else grandSubAll, id, label, kind=wx.ITEM_RADIO)
+            menuItem = wx.MenuItem(bindMenu if bindMenu else grandSubAll, id, label, kind=wx.ITEM_RADIO)
             grandSubAll.Bind(wx.EVT_MENU, self.handleSkillChange, menuItem)
             grandSubAll.Append(menuItem)
 
@@ -130,7 +133,7 @@ class ChangeAffectingSkills(ContextMenuSingle):
                     skillItem.SetBitmap(bitmap)
 
             for i in range(-1, 6):
-                levelItem = self.addSkill(rootMenu if msw else grandSub, skill, i)
+                levelItem = self.addSkill(bindMenu if bindMenu else grandSub, skill, i)
                 grandSub.Append(levelItem)
                 if (not skill.learned and i == -1) or (skill.learned and skill.level == i):
                     levelItem.Check(True)
diff --git a/gui/builtinViews/fittingView.py b/gui/builtinViews/fittingView.py
index ce1fa44a7..d4cbd2ec3 100644
--- a/gui/builtinViews/fittingView.py
+++ b/gui/builtinViews/fittingView.py
@@ -676,9 +676,9 @@ class FittingView(d.Display):
                 itemContext = fullContext[1] if len(fullContext) > 1 else None
                 skillsMenu = ChangeAffectingSkills()
                 if skillsMenu.display(self, srcContext, mainMod):
-                    # Create the submenu directly
-                    rootMenu = wx.Menu()
-                    sub = skillsMenu.getSubMenu(self, srcContext, mainMod, rootMenu, 0, None)
+                    # On Windows, menu items need to be bound to the menu shown with PopupMenu
+                    # We pass None as rootMenu so items are bound to their parent submenus
+                    sub = skillsMenu.getSubMenu(self, srcContext, mainMod, None, 0, None)
                     if sub:
                         self.PopupMenu(sub)
                         return