diff --git a/.ruby-version b/.ruby-version
new file mode 100644
index 0000000..be94e6f
--- /dev/null
+++ b/.ruby-version
@@ -0,0 +1 @@
+3.2.2
diff --git a/lib/code_ownership/private/ownership_mappers/directory_ownership.rb b/lib/code_ownership/private/ownership_mappers/directory_ownership.rb
index 1ac8af9..9bcf26c 100644
--- a/lib/code_ownership/private/ownership_mappers/directory_ownership.rb
+++ b/lib/code_ownership/private/ownership_mappers/directory_ownership.rb
@@ -10,8 +10,6 @@ class DirectoryOwnership
         include Mapper
 
         CODEOWNERS_DIRECTORY_FILE_NAME = '.codeowner'
-        RELATIVE_ROOT = Pathname('.').freeze
-        ABSOLUTE_ROOT = Pathname('/').freeze
 
         @@directory_cache = T.let({}, T::Hash[String, T.nilable(CodeTeams::Team)]) # rubocop:disable Style/ClassVars
 
@@ -76,46 +74,36 @@ def owner_for_codeowners_file(codeowners_file)
           )
         end
 
-        # Takes a file and finds the relevant `.codeowner` file by walking up the directory
+        # takes a file and finds the relevant `.codeowner` file by walking up the directory
         # structure. Example, given `a/b/c.rb`, this looks for `a/b/.codeowner`, `a/.codeowner`,
         # and `.codeowner` in that order, stopping at the first file to actually exist.
-        # If the parovided file is a directory, it will look for `.codeowner` in that directory and then upwards.
-        # We do additional caching so that we don't have to check for file existence every time.
+        # We do additional caching so that we don't have to check for file existence every time
         sig { params(file: String).returns(T.nilable(CodeTeams::Team)) }
         def map_file_to_relevant_owner(file)
           file_path = Pathname.new(file)
-          team = T.let(nil, T.nilable(CodeTeams::Team))
+          path_components = file_path.each_filename.to_a.map { |path| Pathname.new(path) }
 
-          if File.directory?(file)
-            team = get_team_from_codeowners_file_within_directory(file_path)
-          end
-
-          while team.nil? && file_path != RELATIVE_ROOT && file_path != ABSOLUTE_ROOT
-            file_path = file_path.parent
-            team = get_team_from_codeowners_file_within_directory(file_path)
-          end
-
-          team
-        end
+          (path_components.length - 1).downto(0).each do |i|
+            potential_relative_path_name = T.must(path_components[0...i]).reduce(Pathname.new('')) { |built_path, path| built_path.join(path) }
+            potential_codeowners_file = potential_relative_path_name.join(CODEOWNERS_DIRECTORY_FILE_NAME)
 
-        sig { params(directory: Pathname).returns(T.nilable(CodeTeams::Team)) }
-        def get_team_from_codeowners_file_within_directory(directory)
-          potential_codeowners_file = directory.join(CODEOWNERS_DIRECTORY_FILE_NAME)
+            potential_codeowners_file_name = potential_codeowners_file.to_s
 
-          potential_codeowners_file_name = potential_codeowners_file.to_s
+            team = nil
+            if @@directory_cache.key?(potential_codeowners_file_name)
+              team = @@directory_cache[potential_codeowners_file_name]
+            elsif potential_codeowners_file.exist?
+              team = owner_for_codeowners_file(potential_codeowners_file)
 
-          team = nil
-          if @@directory_cache.key?(potential_codeowners_file_name)
-            team = @@directory_cache[potential_codeowners_file_name]
-          elsif potential_codeowners_file.exist?
-            team = owner_for_codeowners_file(potential_codeowners_file)
+              @@directory_cache[potential_codeowners_file_name] = team
+            else
+              @@directory_cache[potential_codeowners_file_name] = nil
+            end
 
-            @@directory_cache[potential_codeowners_file_name] = team
-          else
-            @@directory_cache[potential_codeowners_file_name] = nil
+            return team unless team.nil?
           end
 
-          return team
+          nil
         end
       end
     end
diff --git a/spec/lib/code_ownership/private/ownership_mappers/directory_ownership_spec.rb b/spec/lib/code_ownership/private/ownership_mappers/directory_ownership_spec.rb
index ef1009b..7ef077d 100644
--- a/spec/lib/code_ownership/private/ownership_mappers/directory_ownership_spec.rb
+++ b/spec/lib/code_ownership/private/ownership_mappers/directory_ownership_spec.rb
@@ -21,11 +21,6 @@ module CodeOwnership
       it 'can find the owner of files in a sub-directory of a team-owned directory' do
         expect(CodeOwnership.for_file('a/b/c/c_file.jsx').name).to eq 'Bar'
       end
-
-      it 'looks for codeowner file within directory' do
-        expect(CodeOwnership.for_file('a/b').name).to eq 'Bar'
-        expect(CodeOwnership.for_file(Pathname.pwd.join('a/b').to_s).name).to eq 'Bar'
-      end
     end
   end
 end