diff --git b/bundler/lib/bundler/vendor/connection_pool/lib/connection_pool.rb a/bundler/lib/bundler/vendor/connection_pool/lib/connection_pool.rb
index e680ab363..317088a86 100644
--- b/bundler/lib/bundler/vendor/connection_pool/lib/connection_pool.rb
+++ a/bundler/lib/bundler/vendor/connection_pool/lib/connection_pool.rb
@@ -1,4 +1,4 @@
-require_relative "../../../../../../lib/rubygems/vendor/timeout/lib/timeout"
+require_relative "../../../vendored_timeout"
 require_relative "connection_pool/version"
 
 class Bundler::ConnectionPool
