diff --git a/lib/mix/lib/mix/utils.ex b/lib/mix/lib/mix/utils.ex
index f7739dc195e..18be3e9e3ab 100644
--- a/lib/mix/lib/mix/utils.ex
+++ b/lib/mix/lib/mix/utils.ex
@@ -765,6 +765,11 @@ defmodule Mix.Utils do
           :httpc.set_options([ipfamily: fallback(inet)], :mix)
           request |> httpc_request(http_options) |> httpc_response()
 
+        {:error, {:failed_connect, [{:to_address, _}, {inet, _, reason}]}}
+        when inet in [:inet, :inet6] and elem(reason, 0) == :tls_alert ->
+          http_options = put_in(http_options, [:ssl, :middlebox_comp_mode], false)
+          request |> httpc_request(http_options) |> httpc_response()
+
         response ->
           httpc_response(response)
       end