diff --git a/CHANGELOG.md b/CHANGELOG.md
index 201a7ffc7..692c64787 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -36,6 +36,7 @@ BUG FIXES:
   - providers/virtualbox: Host-only networks set cableconnected property
       to "yes" [GH-3365]
   - provisioners/docker: Use proper flags for 0.9. [GH-3356]
+  - synced\_folders/rsync: Set chmod flag by default on Windows. [GH-3256]
   - synced\_folders/smb: IDs of synced folders are hashed to work better
       with VMware. [GH-3219]
   - synced\_folders/smb: Properly remove existing folders with the
diff --git a/plugins/synced_folders/rsync/helper.rb b/plugins/synced_folders/rsync/helper.rb
index f5c081a74..acc0a6cf0 100644
--- a/plugins/synced_folders/rsync/helper.rb
+++ b/plugins/synced_folders/rsync/helper.rb
@@ -72,6 +72,11 @@ module VagrantPlugins
         args = Array(opts[:args]) if opts[:args]
         args ||= ["--verbose", "--archive", "--delete", "-z"]
 
+        # On Windows, we have to set the chmod flag to avoid permission issues
+        if Vagrant::Util::Platform.windows?
+          args << "--chmod=ugo=rwX"
+        end
+
         # Build up the actual command to execute
         command = [
           "rsync",