diff --git a/plugins/pushes/ftp/push.rb b/plugins/pushes/ftp/push.rb
index 318c26d73..5279c2534 100644
--- a/plugins/pushes/ftp/push.rb
+++ b/plugins/pushes/ftp/push.rb
@@ -21,7 +21,7 @@ module VagrantPlugins
         files = nil
         begin
           files = Hash[*all_files.flat_map do |file|
-              relative_path = relative_path_for(file, config.dir)
+              relative_path = relative_path_for(file, base_dir)
               destination = File.join(config.destination, relative_path)
               file = File.expand_path(file, env.root_path)
               [file, destination]
@@ -31,11 +31,11 @@ module VagrantPlugins
         end
 
         ftp = "#{config.username}@#{config.host}:#{config.destination}"
-        env.ui.info "Uploading #{env.root_path} to #{ftp}"
+        env.ui.info "Uploading #{files.length} files to #{env.root_path} to #{ftp}"
 
         connect do |ftp|
           files.each do |local, remote|
-            @logger.info "Uploading #{local} => #{remote}"
+            env.ui.info "Uploading #{local} => #{remote}"
             ftp.upload(local, remote)
           end
         end
@@ -54,7 +54,7 @@ module VagrantPlugins
       # only returns **files**, not folders or symlinks!
       # @return [Array<String>]
       def all_files
-        files = glob("#{config.dir}/**/*") + includes_files
+        files = glob("#{base_dir}/**/*") + includes_files
         filter_excludes!(files, config.excludes)
         files.reject! { |f| !File.file?(f) }
         files
@@ -64,7 +64,7 @@ module VagrantPlugins
       # @return [Array<String>]
       def includes_files
         includes = config.includes.flat_map do |i|
-          path = absolute_path_for(i, config.dir)
+          path = absolute_path_for(i, base_dir)
           [path, "#{path}/**/*"]
         end
 
@@ -121,6 +121,14 @@ module VagrantPlugins
       rescue ArgumentError
         return path
       end
+
+      def base_dir
+        if Pathname.new(config.dir).absolute?
+          config.dir
+        else
+          File.join(File.expand_path(env.root_path), config.dir)
+        end
+      end
     end
   end
 end
diff --git a/test/unit/plugins/pushes/ftp/push_test.rb b/test/unit/plugins/pushes/ftp/push_test.rb
index b31a57a3e..f1ace1d53 100644
--- a/test/unit/plugins/pushes/ftp/push_test.rb
+++ b/test/unit/plugins/pushes/ftp/push_test.rb
@@ -64,6 +64,9 @@ describe VagrantPlugins::FTPPush::Push do
         .and_return(%w(*.rb))
     end
 
+    after do
+      server.reset
+    end
 
     it "pushes the files to the server" do
       subject.push
@@ -74,6 +77,31 @@ describe VagrantPlugins::FTPPush::Push do
       expect(subject).to receive(:all_files).and_raise(SystemStackError)
       expect{ subject.push }.to raise_error(VagrantPlugins::FTPPush::Errors::TooManyFiles)
     end
+
+    context "when VAGRANT_CWD is set to something relative" do
+      # this will be the PWD for the test context
+      let(:pwd) { Pathname.new(Dir.mktmpdir("vagrant-ftp-push-pwd")) }
+
+      before do
+        # this path should have a ../ in it since the pwd is another temp dir
+        # and measuring path from one to the other. they're most likely to be
+        # siblings
+        relative_path = Pathname.new(@dir).relative_path_from(pwd)
+        allow(env).to receive(:root_path) { relative_path.to_s }
+        # reset config.dir to its default since it was set absolute above
+        allow(config).to receive(:dir) { "." }
+      end
+
+      it "properly paths out the files to upload" do
+        Vagrant::Util::SafeChdir.safe_chdir(pwd) do
+          subject.push
+        end
+
+        expect(server.files).to eq(%w(Gemfile data.txt))
+      ensure
+        FileUtils.rm_rf(pwd)
+      end
+    end
   end
 
   describe "#connect" do