diff --git a/Content.Server/GameObjects/Components/GUI/InventoryComponent.cs b/Content.Server/GameObjects/Components/GUI/InventoryComponent.cs
index 57ab715eb5..a0b86f0625 100644
--- a/Content.Server/GameObjects/Components/GUI/InventoryComponent.cs
+++ b/Content.Server/GameObjects/Components/GUI/InventoryComponent.cs
@@ -10,6 +10,7 @@ using Content.Server.Interfaces.GameObjects;
 using Content.Shared.GameObjects.Components.Inventory;
 using Content.Shared.GameObjects.EntitySystems;
 using Robust.Server.GameObjects.Components.Container;
+using Robust.Shared.Containers;
 using Robust.Shared.GameObjects;
 using Robust.Shared.Interfaces.GameObjects;
 using Robust.Shared.Interfaces.GameObjects.Components;
@@ -115,8 +116,14 @@ namespace Content.Server.GameObjects.Components.GUI
         public override void OnRemove()
         {
             var slots = _slotContainers.Keys.ToList();
+
             foreach (var slot in slots)
             {
+                if (TryGetSlotItem(slot, out ItemComponent item))
+                {
+                    item.Owner.Delete();
+                }
+
                 RemoveSlot(slot);
             }
 
@@ -267,17 +274,17 @@ namespace Content.Server.GameObjects.Components.GUI
             }
 
             var inventorySlot = _slotContainers[slot];
-            var item = inventorySlot.ContainedEntity.GetComponent<ItemComponent>();
-            if (!inventorySlot.Remove(inventorySlot.ContainedEntity))
+            var entity = inventorySlot.ContainedEntity;
+            var item = entity.GetComponent<ItemComponent>();
+            if (!inventorySlot.Remove(entity))
             {
                 return false;
             }
 
             // TODO: The item should be dropped to the container our owner is in, if any.
-            var itemTransform = item.Owner.GetComponent<ITransformComponent>();
-            itemTransform.GridPosition = Owner.GetComponent<ITransformComponent>().GridPosition;
+            ContainerHelpers.AttachParentToContainerOrGrid(entity.Transform);
 
-            _entitySystemManager.GetEntitySystem<InteractionSystem>().UnequippedInteraction(Owner, item.Owner, slot);
+            _entitySystemManager.GetEntitySystem<InteractionSystem>().UnequippedInteraction(Owner, entity, slot);
 
             OnItemChanged?.Invoke();
 
@@ -286,6 +293,29 @@ namespace Content.Server.GameObjects.Components.GUI
             return true;
         }
 
+        public void ForceUnequip(Slots slot)
+        {
+            var inventorySlot = _slotContainers[slot];
+            var entity = inventorySlot.ContainedEntity;
+            if (entity == null)
+            {
+                return;
+            }
+
+            var item = entity.GetComponent<ItemComponent>();
+            inventorySlot.ForceRemove(entity);
+
+            var itemTransform = entity.Transform;
+
+            ContainerHelpers.AttachParentToContainerOrGrid(itemTransform);
+
+            _entitySystemManager.GetEntitySystem<InteractionSystem>().UnequippedInteraction(Owner, item.Owner, slot);
+
+            OnItemChanged?.Invoke();
+
+            Dirty();
+        }
+
         /// <summary>
         ///     Checks whether an item can be dropped from the specified slot.
         /// </summary>
@@ -340,13 +370,11 @@ namespace Content.Server.GameObjects.Components.GUI
                 throw new InvalidOperationException($"Slow '{slot}' does not exist.");
             }
 
-            if (GetSlotItem(slot) != null && !Unequip(slot))
-            {
-                // TODO: Handle this potential failiure better.
-                throw new InvalidOperationException(
-                    "Unable to remove slot as the contained clothing could not be dropped");
-            }
+            ForceUnequip(slot);
 
+            var container = _slotContainers[slot];
+
+            container.Shutdown();
             _slotContainers.Remove(slot);
 
             OnItemChanged?.Invoke();