diff --git a/Content.Client/ContextMenu/UI/ContextMenuPopup.xaml.cs b/Content.Client/ContextMenu/UI/ContextMenuPopup.xaml.cs
index 7376278aa4..6eab81ded2 100644
--- a/Content.Client/ContextMenu/UI/ContextMenuPopup.xaml.cs
+++ b/Content.Client/ContextMenu/UI/ContextMenuPopup.xaml.cs
@@ -58,6 +58,14 @@ namespace Content.Client.ContextMenu.UI
                 DebugTools.Assert(ParentElement.SubMenu == null);
                 ParentElement.SubMenu = this;
             }
+
+            // ensure the menu-stack is properly updated when a pop-up looses focus or otherwise closes without going
+            // through the menu presenter.
+            OnPopupHide += () =>
+            {
+                if (ParentElement != null)
+                    _presenter.CloseSubMenus(ParentElement.ParentMenu);
+            };
         }
 
         protected override void Dispose(bool disposing)
diff --git a/Content.Client/ContextMenu/UI/ContextMenuPresenter.cs b/Content.Client/ContextMenu/UI/ContextMenuPresenter.cs
index 1ad64a4f8c..62e7251861 100644
--- a/Content.Client/ContextMenu/UI/ContextMenuPresenter.cs
+++ b/Content.Client/ContextMenu/UI/ContextMenuPresenter.cs
@@ -2,6 +2,7 @@ using System;
 using System.Collections.Generic;
 using System.Threading;
 using Robust.Client.UserInterface;
+using Robust.Shared.Log;
 using Robust.Shared.Maths;
 using Timer = Robust.Shared.Timing.Timer;
 namespace Content.Client.ContextMenu.UI
@@ -71,6 +72,10 @@ namespace Content.Client.ContextMenu.UI
             {
                 Menus.Pop().Close();
             }
+
+            // ensure no accidental double-closing happens.
+            CancelClose?.Cancel();
+            CancelClose = null;
         }
 
         /// <summary>
@@ -78,7 +83,11 @@ namespace Content.Client.ContextMenu.UI
         /// </summary>
         public virtual void OnMouseEntered(ContextMenuElement element)
         {
-            var topMenu = Menus.Peek();
+            if (!Menus.TryPeek(out var topMenu))
+            {
+                Logger.Error("Context Menu: Mouse entered menu without any open menus?");
+                return;
+            }
 
             if (element.ParentMenu == topMenu || element.SubMenu == topMenu)
                 CancelClose?.Cancel();
@@ -120,8 +129,14 @@ namespace Content.Client.ContextMenu.UI
         /// </remarks>
         public virtual void OpenSubMenu(ContextMenuElement element)
         {
+            if (!Menus.TryPeek(out var topMenu))
+            {
+                Logger.Error("Context Menu: Attempting to open sub menu without any open menus?");
+                return;
+            }
+
             // If This is already the top most menu, do nothing.
-            if (element.SubMenu == Menus.Peek())
+            if (element.SubMenu == topMenu)
                 return;
 
             // Was the parent menu closed or disposed before an open timer completed?
@@ -131,6 +146,10 @@ namespace Content.Client.ContextMenu.UI
             // Close any currently open sub-menus up to this element's parent menu.
             CloseSubMenus(element.ParentMenu);
 
+            // cancel any queued openings to prevent weird double-open scenarios.
+            CancelOpen?.Cancel();
+            CancelOpen = null;
+
             if (element.SubMenu == null)
                 return;
 
@@ -139,8 +158,6 @@ namespace Content.Client.ContextMenu.UI
             var altPos = element.GlobalPosition;
             var pos = altPos + (element.Width + 2*ContextMenuElement.ElementMargin, - 2*ContextMenuElement.ElementMargin);
             element.SubMenu.Open(UIBox2.FromDimensions(pos, (1, 1)), altPos);
-            element.SubMenu.Close();
-            element.SubMenu.Open(UIBox2.FromDimensions(pos, (1, 1)), altPos);
 
             // draw on top of other menus
             element.SubMenu.SetPositionLast();
diff --git a/Content.Client/Verbs/UI/VerbMenuPresenter.cs b/Content.Client/Verbs/UI/VerbMenuPresenter.cs
index b857e1b1bf..9410720719 100644
--- a/Content.Client/Verbs/UI/VerbMenuPresenter.cs
+++ b/Content.Client/Verbs/UI/VerbMenuPresenter.cs
@@ -172,6 +172,7 @@ namespace Content.Client.Verbs.UI
             if (element is not VerbMenuElement verbElement)
                 return;
 
+            args.Handle();
             var verb = verbElement.Verb;
 
             if (verb == null)
@@ -182,8 +183,12 @@ namespace Content.Client.Verbs.UI
                 if (verbElement.SubMenu == null || verbElement.SubMenu.ChildCount == 0)
                     return;
 
-                if (verbElement.SubMenu.MenuBody.Children.First() is not VerbMenuElement verbCategoryElement)
+                if (verbElement.SubMenu.MenuBody.ChildCount != 1
+                    || verbElement.SubMenu.MenuBody.Children.First() is not VerbMenuElement verbCategoryElement)
+                {
+                    OpenSubMenu(verbElement);
                     return;
+                }
 
                 verb = verbCategoryElement.Verb;
 
@@ -194,8 +199,6 @@ namespace Content.Client.Verbs.UI
             _verbSystem.ExecuteVerb(CurrentTarget, verb, verbElement.Type);
             if (verb.CloseMenu)
                 _verbSystem.CloseAllMenus();
-
-            args.Handle();
         }
     }
 }