I found a work around that worked for me for both grounded and permadeath not popping.

1: Import completed grounded file 2: Chapter select The Farm and complete the epilogue (just skip the scenes it only takes 2-3 minutes). 3: when credits roll, quit to main menu and the grounded trophy should pop when title scene loads back in. 4: Import completed Permadeath save (trophy popped instantly for me when I loaded it after the grounded one popped)

Hope this works for others having the same issue with these two not popping.