diff --git a/CHANGELOG.md b/CHANGELOG.md
index a396588e2..fe3f53d23 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,6 +1,7 @@
 ## 0.8.8 (unreleased)
 
-
+  - Mount shared folders shortest to longest to avoid mounting
+    subfolders first. [GH-525]
 
 ## 0.8.7 (September 13, 2011)
 
diff --git a/lib/vagrant/action/vm/share_folders.rb b/lib/vagrant/action/vm/share_folders.rb
index c4ce6cc14..04ec62120 100644
--- a/lib/vagrant/action/vm/share_folders.rb
+++ b/lib/vagrant/action/vm/share_folders.rb
@@ -52,7 +52,17 @@ module Vagrant
 
           @env["vm"].ssh.execute do |ssh|
             # short guestpaths first, so we don't step on ourselves
-            shared_folders.sort_by {|name, data| data[:guestpath].length}.each do |name, data|
+            folders = shared_folders.sort_by do |name, data|
+              if data[:guestpath]
+                data[:guestpath].length
+              else
+                # A long enough path to just do this at the end.
+                10000
+              end
+            end
+
+            # Go through each folder and mount
+            folders.each do |name, data|
               if data[:guestpath]
                 # Guest path specified, so mount the folder to specified point
                 @env.ui.info(I18n.t("vagrant.actions.vm.share_folders.mounting_entry",