diff --git a/plugins/pushes/ftp/errors.rb b/plugins/pushes/ftp/errors.rb
new file mode 100644
index 000000000..111dd83af
--- /dev/null
+++ b/plugins/pushes/ftp/errors.rb
@@ -0,0 +1,13 @@
+module VagrantPlugins
+  module FTPPush
+    module Errors
+      class Error < Vagrant::Errors::VagrantError
+        error_namespace("ftp_push.errors")
+      end
+
+      class TooManyFiles < Error
+        error_key(:too_many_files)
+      end
+    end
+  end
+end
diff --git a/plugins/pushes/ftp/locales/en.yml b/plugins/pushes/ftp/locales/en.yml
index 0bbbe51f1..c5ba39869 100644
--- a/plugins/pushes/ftp/locales/en.yml
+++ b/plugins/pushes/ftp/locales/en.yml
@@ -9,3 +9,8 @@ en:
             config.push.define "ftp" do |push|
               push.%{attribute} = "..."
             end
+      too_many_files: |-
+        The configured directory for Vagrant FTP push contains too many files
+        to successfully complete the command. This can be resolved by either
+        removing extraneous files from the configured directory, or updating
+        the `dir` configuration option to a subdirectory.
diff --git a/plugins/pushes/ftp/push.rb b/plugins/pushes/ftp/push.rb
index 755304ee6..318c26d73 100644
--- a/plugins/pushes/ftp/push.rb
+++ b/plugins/pushes/ftp/push.rb
@@ -2,6 +2,7 @@ require "net/ftp"
 require "pathname"
 
 require_relative "adapter"
+require_relative "errors"
 
 module VagrantPlugins
   module FTPPush
@@ -17,12 +18,17 @@ module VagrantPlugins
       def push
         # Grab files early so if there's an exception or issue, we don't have to
         # wait and close the (S)FTP connection as well
-        files = Hash[*all_files.flat_map do |file|
-          relative_path = relative_path_for(file, config.dir)
-          destination = File.join(config.destination, relative_path)
-          file = File.expand_path(file, env.root_path)
-          [file, destination]
-        end]
+        files = nil
+        begin
+          files = Hash[*all_files.flat_map do |file|
+              relative_path = relative_path_for(file, config.dir)
+              destination = File.join(config.destination, relative_path)
+              file = File.expand_path(file, env.root_path)
+              [file, destination]
+            end]
+        rescue SystemStackError
+          raise Errors::TooManyFiles
+        end
 
         ftp = "#{config.username}@#{config.host}:#{config.destination}"
         env.ui.info "Uploading #{env.root_path} to #{ftp}"
diff --git a/test/unit/plugins/pushes/ftp/push_test.rb b/test/unit/plugins/pushes/ftp/push_test.rb
index ba69e0078..83509fb7d 100644
--- a/test/unit/plugins/pushes/ftp/push_test.rb
+++ b/test/unit/plugins/pushes/ftp/push_test.rb
@@ -73,6 +73,11 @@ describe VagrantPlugins::FTPPush::Push do
       subject.push
       expect(server.files).to eq(%w(Gemfile data.txt))
     end
+
+    it "raises informative exception when too many files to process" do
+      expect(subject).to receive(:all_files).and_raise(SystemStackError)
+      expect{ subject.push }.to raise_error(VagrantPlugins::FTPPush::Errors::TooManyFiles)
+    end
   end
 
   describe "#connect" do