diff --git a/spec/context-menu-manager-spec.coffee b/spec/context-menu-manager-spec.coffee
index a0cb69485..9c3c02175 100644
--- a/spec/context-menu-manager-spec.coffee
+++ b/spec/context-menu-manager-spec.coffee
@@ -68,6 +68,8 @@ describe "ContextMenuManager", ->
         '.grandchild.foo': [{label: 'A', command: 'b'}]
       disposable3 = contextMenu.add
         '.grandchild': [{label: 'A', command: 'c'}]
+      disposable4 = contextMenu.add
+        '.child': [{label: 'A', command: 'd'}]
 
       expect(contextMenu.templateForElement(grandchild)).toEqual [{label: 'A', command: 'b'}]
 
@@ -77,6 +79,9 @@ describe "ContextMenuManager", ->
       disposable3.dispose()
       expect(contextMenu.templateForElement(grandchild)).toEqual [{label: 'A', command: 'a'}]
 
+      disposable1.dispose()
+      expect(contextMenu.templateForElement(grandchild)).toEqual [{label: 'A', command: 'd'}]
+
     it "allows multiple separators", ->
       contextMenu.add
         '.grandchild': [
diff --git a/src/context-menu-manager.coffee b/src/context-menu-manager.coffee
index f39cd8b18..1f00c5e7a 100644
--- a/src/context-menu-manager.coffee
+++ b/src/context-menu-manager.coffee
@@ -10,7 +10,6 @@ Grim = require 'grim'
 MenuHelpers = require './menu-helpers'
 
 SpecificityCache = {}
-SequenceCount = 0
 
 # Extended: Provides a registry for commands that you'd like to appear in the
 # context menu.
@@ -91,7 +90,7 @@ class ContextMenuManager
     addedItemSets = []
 
     for selector, items of itemsBySelector
-      itemSet = new ContextMenuItemSet(selector, items.slice())
+      itemSet = new ContextMenuItemSet(selector, items)
       addedItemSets.push(itemSet)
       @itemSets.push(itemSet)
 
@@ -107,19 +106,21 @@ class ContextMenuManager
     currentTarget = event.target
 
     while currentTarget?
+      currentTargetItems = []
       matchingItemSets =
-        @itemSets
-          .filter (itemSet) -> currentTarget.webkitMatchesSelector(itemSet.selector)
-          .sort (a, b) -> a.compare(b)
+        @itemSets.filter (itemSet) -> currentTarget.webkitMatchesSelector(itemSet.selector)
 
-      for {items} in matchingItemSets
-        for item in items
+      for itemSet in matchingItemSets
+        for item in itemSet.items
           continue if item.devMode and not @devMode
           item = Object.create(item)
           if typeof item.shouldDisplay is 'function'
             continue unless item.shouldDisplay(event)
           item.created?(event)
-          MenuHelpers.merge(template, MenuHelpers.cloneMenuItem(item))
+          MenuHelpers.merge(currentTargetItems, MenuHelpers.cloneMenuItem(item), itemSet.specificity)
+
+      for item in currentTargetItems
+        MenuHelpers.merge(template, item, false)
 
       currentTarget = currentTarget.parentElement
 
@@ -167,9 +168,3 @@ class ContextMenuManager
 class ContextMenuItemSet
   constructor: (@selector, @items) ->
     @specificity = (SpecificityCache[@selector] ?= specificity(@selector))
-    @sequenceNumber = SequenceCount++
-
-  # more specific / recent item sets sort later, because we clobber existing menu items
-  compare: (other) ->
-    @specificity - other.specificity or
-      @sequenceNumber - other.sequenceNumber
diff --git a/src/menu-helpers.coffee b/src/menu-helpers.coffee
index c7b449112..a8fd26a50 100644
--- a/src/menu-helpers.coffee
+++ b/src/menu-helpers.coffee
@@ -1,14 +1,18 @@
 _ = require 'underscore-plus'
 
-merge = (menu, item) ->
+ItemSpecificities = new WeakMap
+
+merge = (menu, item, itemSpecificity=Infinity) ->
+  ItemSpecificities.set(item, itemSpecificity) if itemSpecificity
   matchingItemIndex = findMatchingItemIndex(menu, item)
   matchingItem = menu[matchingItemIndex] unless matchingItemIndex is - 1
 
   if matchingItem?
     if item.submenu?
-      merge(matchingItem.submenu, submenuItem) for submenuItem in item.submenu
-    else
-      menu[matchingItemIndex] = item
+      merge(matchingItem.submenu, submenuItem, itemSpecificity) for submenuItem in item.submenu
+    else if itemSpecificity
+      unless itemSpecificity < ItemSpecificities.get(matchingItem)
+        menu[matchingItemIndex] = item
   else
     menu.push(item)