diff --git a/src/net/tools/naive/naive_proxy_delegate.cc b/src/net/tools/naive/naive_proxy_delegate.cc
index 3c246d06f2..c52ed7b4cc 100644
--- a/src/net/tools/naive/naive_proxy_delegate.cc
+++ b/src/net/tools/naive/naive_proxy_delegate.cc
@@ -160,6 +160,8 @@ std::optional<PaddingType> NaiveProxyDelegate::GetProxyChainPaddingType(
   // protocols.
   if (proxy_chain.is_direct())
     return PaddingType::kNone;
+  if (proxy_chain.Last().is_socks())
+    return PaddingType::kNone;
   return padding_type_by_server_[proxy_chain.Last()];
 }