diff --git a/Content.Server/GameObjects/Components/GUI/InventoryComponent.cs b/Content.Server/GameObjects/Components/GUI/InventoryComponent.cs
index 37542f6469..49a82f609d 100644
--- a/Content.Server/GameObjects/Components/GUI/InventoryComponent.cs
+++ b/Content.Server/GameObjects/Components/GUI/InventoryComponent.cs
@@ -4,6 +4,7 @@ using System.Linq;
 using Content.Server.GameObjects.EntitySystems;
 using Content.Shared.GameObjects;
 using Robust.Server.GameObjects.Components.Container;
+using Robust.Server.Interfaces.GameObjects;
 using Robust.Server.Interfaces.Player;
 using Robust.Shared.GameObjects;
 using Robust.Shared.Interfaces.GameObjects;
@@ -14,6 +15,7 @@ using Robust.Shared.Utility;
 using Robust.Shared.ViewVariables;
 using static Content.Shared.GameObjects.Components.Inventory.EquipmentSlotDefines;
 using static Content.Shared.GameObjects.SharedInventoryComponent.ClientInventoryMessage;
+using IComponent = Robust.Shared.Interfaces.GameObjects.IComponent;
 
 namespace Content.Server.GameObjects
 {
@@ -222,6 +224,24 @@ namespace Content.Server.GameObjects
             return SlotContainers.ContainsKey(slot);
         }
 
+        /// <summary>
+        /// The underlying Container System just notified us that an entity was removed from it.
+        /// We need to make sure we process that removed entity as being unequpped from the slot.
+        /// </summary>
+        private void ForceUnequip(IContainer container, IEntity entity)
+        {
+            // make sure this is one of our containers.
+            // Technically the correct way would be to enumerate the possible slot names
+            // comparing with this container, but I might as well put the dictionary to good use.
+            if (!(container is ContainerSlot slot) || !SlotContainers.ContainsValue(slot))
+                return;
+
+            if (entity.TryGetComponent(out ItemComponent itemComp))
+                itemComp.RemovedFromSlot();
+
+            Dirty();
+        }
+
         /// <summary>
         /// Message that tells us to equip or unequip items from the inventory slots
         /// </summary>
@@ -291,6 +311,11 @@ namespace Content.Server.GameObjects
                     if (item != null && item.Owner.TryGetComponent(out ServerStorageComponent storage))
                         storage.OpenStorageUI(Owner);
                     break;
+
+                case ContainerContentsModifiedMessage msg:
+                    if (msg.Removed)
+                        ForceUnequip(msg.Container, msg.Entity);
+                    break;
             }
         }
 
diff --git a/RobustToolbox b/RobustToolbox
index 566ed9cbdc..c8ff91bf72 160000
--- a/RobustToolbox
+++ b/RobustToolbox
@@ -1 +1 @@
-Subproject commit 566ed9cbdc63465b69b1f65bb09c8d42cf2b5ff0
+Subproject commit c8ff91bf72969053ac06711e3b0cd28d86fe2ba4