After a small escalation support was able to pin point the ( multiple ) issues.
1- There is a bug in MR28.X that prevents an AP from changing it's "signing" URL when there is a shard change/split.
2- We had a shard split in July
So our APs were still pointing to the 'old' shard , tried to renew their cert and failed. They have to be rebooted to point to the new shard , download the new cert and voilà.
TL;DR : When Meraki is doing shard splits , they should check if customers are running MR28.X + SecurePort. That would avoid the mess that we are ( still ) experiencing.
Cheers !