I had the same problem recently on raspberry pi 2, every time upgrade process and need to reboot, it is failed to boot up . Seems issue with boot record on first partition. What I did is fixing it with fsck or dosfsck the first partition, there are 2 things usually happened, one is boot record issue, just chooese copy from backup, and the second thing is regarding parity or flag. Just chose to fix it, and first step are done. Then in the second step check and finx the second partition using e2fsck, once done most of the case ready to go, just plug in back to the raspi and it will boot again.
But it was never happened on my orange pi zero 3 and orange pi 5 plus.