diff --git a/lib/licensed/sources/bundler.rb b/lib/licensed/sources/bundler.rb
index 0e894200..b2a80c3a 100644
--- a/lib/licensed/sources/bundler.rb
+++ b/lib/licensed/sources/bundler.rb
@@ -109,9 +109,11 @@ def with_application_environment
 
             # reset bundler to load from the current app's source path
             ::Bundler.reset!
-            ::Bundler.load
           end
 
+          # ensure the bundler environment is loaded before enumeration
+          ::Bundler.load
+
           yield
         end
       ensure
@@ -119,8 +121,10 @@ def with_application_environment
           # restore bundler configuration
           ENV.replace(backup)
           ::Bundler.reset!
-          ::Bundler.load
         end
+
+        # reload the bundler environment after enumeration
+        ::Bundler.load
       end
 
       # Returns whether the current licensed execution is running ruby-packer