diff --git a/CHANGELOG.md b/CHANGELOG.md
index ca77a22e4..21d20f7fc 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,8 @@
 
 BUG FIXES:
 
+  - core: Randomize some filenames internally to improve the parallelism
+      of Vagrant. [GH-3386]
   - core: Don't error if network problems cause box update check to
       fail [GH-3391]
   - guests/fedora: Fix hostname setting. [GH-3382]
diff --git a/lib/vagrant/environment.rb b/lib/vagrant/environment.rb
index 68168d4d6..21e06bd3d 100644
--- a/lib/vagrant/environment.rb
+++ b/lib/vagrant/environment.rb
@@ -516,7 +516,8 @@ module Vagrant
 
       # Attempt to write into the home directory to verify we can
       begin
-        path = @home_path.join("perm_test")
+        suffix = (0...32).map { (65 + rand(26)).chr }.join
+        path   = @home_path.join("perm_test_#{suffix}")
         path.open("w") do |f|
           f.write("hello")
         end