diff --git a/lib/rubocop/file_finder.rb b/lib/rubocop/file_finder.rb
index 05dbb3ccd0aa..b6724f791636 100644
--- a/lib/rubocop/file_finder.rb
+++ b/lib/rubocop/file_finder.rb
@@ -32,10 +32,10 @@ def find_last_file_upwards(filename, start_dir)
 
     def traverse_files_upwards(filename, start_dir)
       Pathname.new(start_dir).expand_path.ascend do |dir|
-        break if FileFinder.root_level?(dir)
-
         file = dir + filename
         yield(file.to_s) if file.exist?
+
+        break if FileFinder.root_level?(dir)
       end
     end
   end
diff --git a/lib/rubocop/rspec/shared_contexts.rb b/lib/rubocop/rspec/shared_contexts.rb
index d3fb2081d60e..7bc0b59349f0 100644
--- a/lib/rubocop/rspec/shared_contexts.rb
+++ b/lib/rubocop/rspec/shared_contexts.rb
@@ -12,16 +12,17 @@
       # get mismatched pathnames when loading config files later on.
       tmpdir = File.realpath(tmpdir)
 
+      virtual_home = File.expand_path(File.join(tmpdir, 'home'))
+      Dir.mkdir(virtual_home)
+      ENV['HOME'] = virtual_home
+      ENV.delete('XDG_CONFIG_HOME')
+
+      working_dir = File.join(tmpdir, 'work')
+
       # Make upwards search for .rubocop.yml files stop at this directory.
-      RuboCop::FileFinder.root_level = tmpdir
+      RuboCop::FileFinder.root_level = working_dir
 
       begin
-        virtual_home = File.expand_path(File.join(tmpdir, 'home'))
-        Dir.mkdir(virtual_home)
-        ENV['HOME'] = virtual_home
-        ENV.delete('XDG_CONFIG_HOME')
-
-        working_dir = File.join(tmpdir, 'work')
         Dir.mkdir(working_dir)
 
         Dir.chdir(working_dir) do