diff --git a/features/codedeploy-local/codedeploy_local.feature b/features/codedeploy-local/codedeploy_local.feature
index 14d72b5f..6b0f871d 100644
--- a/features/codedeploy-local/codedeploy_local.feature
+++ b/features/codedeploy-local/codedeploy_local.feature
@@ -31,6 +31,13 @@ Feature: Local Deploy using AWS CodeDeploy Local CLI
     And the expected files should have have been locally deployed to my host
     And the scripts should have been executed during local deployment
 
+  Scenario: Doing a sample local deployment using a zipped_directory bundle
+    Given I have a sample local zipped_directory bundle
+    When I create a local deployment with my bundle
+    Then the local deployment command should succeed
+    And the expected files should have have been locally deployed to my host
+    And the scripts should have been executed during local deployment
+
   Scenario: Doing a sample local deployment using a tgz bundle
     Given I have a sample local tgz bundle
     When I create a local deployment with my bundle
diff --git a/features/step_definitions/codedeploy_local_steps.rb b/features/step_definitions/codedeploy_local_steps.rb
index d12d2410..0985ef2b 100644
--- a/features/step_definitions/codedeploy_local_steps.rb
+++ b/features/step_definitions/codedeploy_local_steps.rb
@@ -21,7 +21,7 @@
   FileUtils.rm_rf(@test_directory) unless @test_directory.nil?
 end
 
-Given(/^I have a sample local (tgz|tar|zip|directory|relative_directory|custom_event_directory|directory_with_destination_files) bundle$/) do |bundle_type|
+Given(/^I have a sample local (tgz|tar|zip|zipped_directory|directory|relative_directory|custom_event_directory|directory_with_destination_files) bundle$/) do |bundle_type|
   case bundle_type
   when 'custom_event_directory'
     @bundle_original_directory_location = StepConstants::SAMPLE_CUSTOM_EVENT_APP_BUNDLE_FULL_PATH
@@ -32,13 +32,15 @@
   end
 
   expect(File.directory?(@bundle_original_directory_location)).to be true
-  @bundle_type = bundle_type.include?('directory') ? 'directory' : bundle_type
+  @bundle_type = bundle_type.include?('zip') ? 'zip' : (bundle_type.include?('directory') ? 'directory' : bundle_type)
 
   case bundle_type
   when 'relative_directory'
     @bundle_location = Pathname.new(@bundle_original_directory_location).relative_path_from Pathname.getwd
   when 'zip'
     @bundle_location = zip_app_bundle(@test_directory)
+  when 'zipped_directory'
+    @bundle_location = zip_app_dir_bundle(@test_directory)
   when 'tar'
     @bundle_location = tar_app_bundle(@test_directory)
   when 'tgz'
@@ -50,6 +52,19 @@
   expect(File.file?(@bundle_location)).to be true unless bundle_type.include? 'directory'
 end
 
+# Create a zip of the bundle with a nested directory containing the actual bundle files
+def zip_app_dir_bundle(temp_directory_to_create_bundle)
+  zip_file_name = "#{temp_directory_to_create_bundle}/app_dir_bundle.zip"
+  Dir.mktmpdir { |zip_build_dir|
+    # Copy the bundle files into a temporary directory so we can just zip the sample bundle
+    FileUtils.cp_r(StepConstants::SAMPLE_APP_BUNDLE_FULL_PATH, zip_build_dir)
+    zip_directory(zip_build_dir, zip_file_name)
+  }
+  # Confirm appspec.yml is not at top level
+  Zip::File.open(zip_file_name) { |zip| expect(zip.entries.map(&:name).include? "appspec.yml").to be false }
+  zip_file_name
+end
+
 def tar_app_bundle(temp_directory_to_create_bundle)
   tar_file_name = "#{temp_directory_to_create_bundle}/app_bundle.tar"
   old_direcory = Dir.pwd
diff --git a/lib/instance_agent/plugins/codedeploy/command_executor.rb b/lib/instance_agent/plugins/codedeploy/command_executor.rb
index b8587e24..a97a58be 100644
--- a/lib/instance_agent/plugins/codedeploy/command_executor.rb
+++ b/lib/instance_agent/plugins/codedeploy/command_executor.rb
@@ -374,16 +374,7 @@ def handle_local_directory(deployment_spec, local_location)
 
         private
         def unpack_bundle(cmd, bundle_file, deployment_spec)
-          strip_leading_directory = deployment_spec.revision_source == 'GitHub'
-
-          if strip_leading_directory
-            # Extract to a temporary directory first so we can move the files around
-            dst = File.join(deployment_root_dir(deployment_spec), 'deployment-archive-temp')
-            actual_dst = File.join(deployment_root_dir(deployment_spec), 'deployment-archive')
-            FileUtils.rm_rf(dst)
-          else
-            dst = File.join(deployment_root_dir(deployment_spec), 'deployment-archive')
-          end
+          dst = File.join(deployment_root_dir(deployment_spec), 'deployment-archive')
 
           if "tar".eql? deployment_spec.bundle_type
             InstanceAgent::Platform.util.extract_tar(bundle_file, dst)
@@ -407,26 +398,27 @@ def unpack_bundle(cmd, bundle_file, deployment_spec)
             InstanceAgent::Platform.util.extract_tar(bundle_file, dst)
           end
 
-          if strip_leading_directory
-            log(:info, "Stripping leading directory from archive bundle contents.")
-
-            # Find leading directory to remove
-            archive_root_files = Dir.entries(dst)
-            archive_root_files.delete_if { |name| name == '.' || name == '..' }
+          archive_root_files = Dir.entries(dst)
+          archive_root_files.delete_if { |name| name == '.' || name == '..' }
 
-            if (archive_root_files.size != 1)
-              log(:warn, "Expected archive to have a single root directory containing the actual bundle root, but it had #{archive_root_files.size} entries instead. Skipping leading directory removal and using archive as is.")
-              FileUtils.mv(dst, actual_dst)
-              return
-            end
-
-            nested_archive_root = File.join(dst, archive_root_files[0])
-            log(:debug, "Actual archive root at #{nested_archive_root}. Moving to #{actual_dst}")
-
-            FileUtils.mv(nested_archive_root, actual_dst)
-            FileUtils.rmdir(dst)
-
-            log(:debug, Dir.entries(actual_dst).join("; "))
+          # If the top level of the archive is a directory that contains an appspec,
+          # strip that before giving up
+          if ((archive_root_files.size == 1) && 
+              File.directory?(File.join(dst, archive_root_files[0])) &&
+              Dir.entries(File.join(dst, archive_root_files[0])).grep(/appspec/i).any?)
+            log(:info, "Stripping leading directory from archive bundle contents.")
+            # Move the unpacked files to a temporary location
+            tmp_dst = File.join(deployment_root_dir(deployment_spec), 'deployment-archive-temp')
+            FileUtils.rm_rf(tmp_dst)
+            FileUtils.mv(dst, tmp_dst)
+
+            # Move the top level directory to the intended location
+            nested_archive_root = File.join(tmp_dst, archive_root_files[0])
+            log(:debug, "Actual archive root at #{nested_archive_root}. Moving to #{dst}")
+            FileUtils.mv(nested_archive_root, dst)
+            FileUtils.rmdir(tmp_dst)
+
+            log(:debug, Dir.entries(dst).join("; "))            
           end
         end