diff --git a/lib/brakeman.rb b/lib/brakeman.rb
index b549c224b3..e002b0f713 100644
--- a/lib/brakeman.rb
+++ b/lib/brakeman.rb
@@ -362,7 +362,14 @@ def self.scan options
   end
 
   def self.write_report_to_files tracker, output_files
+    require 'fileutils'
+
     output_files.each_with_index do |output_file, idx|
+      dir = File.dirname(output_file)
+      unless Dir.exist? dir
+        FileUtils.mkdir_p(dir)
+      end
+
       File.open output_file, "w" do |f|
         f.write tracker.report.format(tracker.options[:output_formats][idx])
       end
diff --git a/test/tests/json_compare.rb b/test/tests/json_compare.rb
index 452063a8cd..10a1cc1c67 100644
--- a/test/tests/json_compare.rb
+++ b/test/tests/json_compare.rb
@@ -5,14 +5,15 @@ class JSONCompareTests < Minitest::Test
 
   def setup
     @path = File.expand_path "#{TEST_PATH}/apps/rails3.2"
-    @json_path = File.join @path, "report.json"
-    File.delete @json_path if File.exist? @json_path
+    @json_path = File.join @path, "doesnt_exist", "report.json"
+    teardown # just to be sure
     Brakeman.run :app_path => @path, :output_files => [@json_path]
     @report = JSON.parse File.read(@json_path)
   end
 
   def teardown
     File.delete @json_path if File.exist? @json_path
+    Dir.delete File.dirname(@json_path) if Dir.exist? File.dirname(@json_path)
   end
 
   def update_json