Hey everyone,
I had the same problem and I find a workaround with Javascript. Not ideal, but it fixes the problem.
I just added this in my footer :
<script>
const freeshipping = document.getElementById("shipping_method_0_free_shipping13");
if(freeshipping != null){
fs.setAttribute("checked","checked")
}
</script>
You’have to change shipping_method_0_free_shipping13 with which ever ID is on your install. You can inspect your Free Shipping checkbox to find the ID.
To my understanding the problem comes form the fact tha tonce the shipping opition is set once, if a new conditional option is added, then it’s not updating. It might be set in cache or a cookie and the method to reassign the shipping is not called for some reason.
Hope that will help someone.