diff --git a/lib/vagrant/util/platform.rb b/lib/vagrant/util/platform.rb
index 3c0ecf420..9931c40f1 100644
--- a/lib/vagrant/util/platform.rb
+++ b/lib/vagrant/util/platform.rb
@@ -392,7 +392,7 @@ module Vagrant
         # @param [String, Pathname] path Path to convert
         # @return [String]
         def wsl_to_windows_path(path)
-          path = path.to_s
+          path = File.expand_path(path.to_s)
           if wsl? && wsl_windows_access? && !path.match(/^[a-zA-Z]:/)
             if wsl_path?(path)
               parts = path.split("/")
@@ -403,17 +403,15 @@ module Vagrant
               if root_path.end_with?("lxss") && !(["root", "home"].include?(parts.first))
                 root_path = "#{root_path}\\rootfs"
               end
-              [root_path, *parts].join("\\")
+              path = [root_path, *parts].join("\\")
             else
               path = path.to_s.sub("/mnt/", "")
               parts = path.split("/")
               parts.first << ":"
               path = parts.join("\\")
-              path
             end
-          else
-            path
           end
+          path
         end
 
         # Takes a windows path and formats it to the