Is It Okay to Ask God for the Repentance of Someone Who Has Passed Away?

Questions about asking God for the repentance of someone who has passed away, how to respond to a request to pray for a deceased person, reconciling Hebrews 9:27 with people who have died twice, and whether we’ll be judged according to the revelation we received. What are your thoughts on asking God for the repentance of someone who has passed away? When asked to pray for a friend’s deceased mother’s soul, what is a compassionate response that may lead to an opportunity to share the gospel? How do we reconcile Hebrews 9:27, which says it’s appointed for each of us to die once, with people being raised from the dead by Jesus, Peter, and Paul and then dying a second time? Are people judged differently by God according to the revelation they received?