diff --git a/CHANGELOG.md b/CHANGELOG.md
index 979ad1cf6..dcb3f8ff8 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -40,6 +40,7 @@ BUG FIXES:
   - provisioners/chef-zero: support more chef-zero/local mode attributes [GH-5339]
   - provisioners/docker: use docker.com instead of docker.io [GH-5216]
   - pushes/atlas: send additional box metadata [GH-5283]
+  - pushes/ftp: improve check for remote directory existence [GH-5549]
   - synced\_folders/rsync: add `IdentitiesOnly=yes` to the rsync command. [GH-5175]
   - virtualbox/config: fix misleading error message for private_network [GH-5536, GH-5418]
 
diff --git a/plugins/pushes/ftp/adapter.rb b/plugins/pushes/ftp/adapter.rb
index 8a9414376..d0d076491 100644
--- a/plugins/pushes/ftp/adapter.rb
+++ b/plugins/pushes/ftp/adapter.rb
@@ -74,7 +74,7 @@ module VagrantPlugins
 
         # Create the parent directories if they does not exist (naive mkdir -p)
         fullpath.descend do |path|
-          if @server.list(path.to_s).empty?
+          if !directory_exists?(path.to_s)
             @server.mkdir(path.to_s)
           end
         end
@@ -83,6 +83,15 @@ module VagrantPlugins
         @server.putbinaryfile(local, remote)
       end
 
+      def directory_exists?(path)
+        begin
+          @server.chdir(path)
+          return true
+        rescue Net::FTPPermError
+          return false
+        end
+      end
+
       private
 
       def pwd