diff --git a/code/_onclick/hud/screen_objects.dm b/code/_onclick/hud/screen_objects.dm
index 56db868a21..2f5f4a3dd4 100644
--- a/code/_onclick/hud/screen_objects.dm
+++ b/code/_onclick/hud/screen_objects.dm
@@ -154,8 +154,8 @@
 	if(hud?.mymob && slot_id)
 		var/obj/item/inv_item = hud.mymob.get_item_by_slot(slot_id)
 		if(inv_item)
-			if(hud?.mymob.incapacitated())
-				inv_item.apply_outline(COLOR_RED_GRAY)
+			if(hud?.mymob.incapacitated() || (slot_id in hud?.mymob.check_obscured_slots()) || !hud?.mymob.canUnEquip(inv_item))
+				inv_item.apply_outline(_size = 3)
 			else
 				inv_item.apply_outline()
 
diff --git a/code/game/objects/items.dm b/code/game/objects/items.dm
index 7177249dbc..0d6b1231fc 100644
--- a/code/game/objects/items.dm
+++ b/code/game/objects/items.dm
@@ -890,8 +890,8 @@ GLOBAL_VAR_INIT(embedpocalypse, FALSE) // if true, all items will be able to emb
 		var/user = usr
 		tip_timer = addtimer(CALLBACK(src, .proc/openTip, location, control, params, user), timedelay, TIMER_STOPPABLE)//timer takes delay in deciseconds, but the pref is in milliseconds. dividing by 100 converts it.
 	var/mob/living/L = usr
-	if(istype(L) && L.incapacitated())
-		apply_outline(COLOR_RED_GRAY)
+	if(istype(L) && (L.incapacitated() || (current_equipped_slot in L.check_obscured_slots()) || !L.canUnEquip(src)))
+		apply_outline(_size = 3)
 	else
 		apply_outline()
 
@@ -905,7 +905,7 @@ GLOBAL_VAR_INIT(embedpocalypse, FALSE) // if true, all items will be able to emb
 	closeToolTip(usr)
 	remove_outline()
 
-/obj/item/proc/apply_outline(colour = null)
+/obj/item/proc/apply_outline(colour = null, _size=1)
 	if(!(item_flags & IN_INVENTORY || item_flags & IN_STORAGE) || QDELETED(src) || isobserver(usr))
 		return
 	if(usr.client)
@@ -920,7 +920,7 @@ GLOBAL_VAR_INIT(embedpocalypse, FALSE) // if true, all items will be able to emb
 			colour = COLOR_BLUE_GRAY
 	if(outline_filter)
 		filters -= outline_filter
-	outline_filter = filter(type="outline", size=1, color=colour)
+	outline_filter = filter(type="outline", size=_size, color=colour)
 	filters += outline_filter
 
 /obj/item/proc/remove_outline()