Can you definitively know if you actually obtained an indulgence?

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I’m not sure if this is the correct place to post this, and please do correct me if I’m wrong. But what I’d like to know is if it is possible to know if you have actually obtained an indulgence. I know that there are certain requirements–Confession, detachment from sin, receiving the Eucharist, etc.–but I want to focus on the “detachment from sin” part. Is it possible to objectively know if you have done this? Is this simple to do (in other words, am I overthinking this)?

Also, I have been trying to answer each of Luther’s 95 theses in an attempt to evangelize to my staunchly Lutheran family, and I came across one in particular that posits a related question: “Why are funeral and anniversary masses for the dead continued and why does he not return or permit the withdrawal of the endowments founded for them, since it is wrong to pray for the redeemed?”

Could someone please help me? If you have sources, kindly link them. Thanks!
 
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Is it possible to objectively know if you have done this? Is this simple to do (in other words, am I overthinking this)?
You just do the best you can and have faith. I’m not sure what you mean by “objectively know”. It’s not like you can stick your finger on a touchpad and have a green light flash on if you were sufficiently detached from sin to get a 100 percent plenary.

“Detachment from sin” is not hard; people do tend to overthink it and make a big deal out of it.
It just means you are working hard to detach yourself from ALL sins and not stubbornly holding on to some sin that you don’t want to overcome.


Most of us are not certain if we’re totally detached from sin or not, so again we just do our best and hope for the best. If you are constantly doing indulgenced works you’re naturally going to gravitate away from sin anyway because you will be getting grace through doing all the prayers, confessions, Holy Communions and so forth.
 
You follow the teaching of the Catholic Church and trust in Divine Providence.

We can’t buy indulgences or someone-else’s prayer. A Mass stipend is to support the living expenses of the priest and can be waived if the priest thinks it’s appropriate.

I have always maintained that it is a grave sin to charge someone to enter a church and I will not enter European Cathedrals that have an admission charge. I go to Mass elsewhere. When I was asked for a fee to enter the Kaiserdom (Lutheran Cathedral) in Berlin, I turned and walked away. Perhaps I should have nailed my theses to the door.
 
I’m also not sure if we still have “endowments” for Masses for the dead. If you want to have Masses said, then you pay a stipend per Mass which as jimXroberts said can be waived. If you want to enroll your dead loved one into some kind of perpetual Mass society, you generally make a one-time donation that is not huge, the person’s name then goes on the list in perpetuity and it’s understood that once the person has gone to Heaven, God will transfer the benefits to some other soul in need. You essentially just donated to the Church, I don’t think anybody doing this expects to get a refund of their 50 dollar donation or whatever. It’s not like you have to donate your whole estate to the Church to have Masses said for your loved one’s soul over the long term.
 
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Sorry I wasn’t clear–the context is that Luther was upset because there were masses being said for people that presumably were in heaven because someone had received an indulgence and imparted it on them, and it is wrong to pray for those already in heaven (i.e. the saints).
So am I understanding this correctly if I were to say that we pray for them anyway because we cannot know with certainty where they are on their spiritual journey, and if they are indeed in heaven, our prayers for them will by no means offend God, and the fruits of those prayers will instead be conferred on some other soul in need?
 
No prayer is ever wasted.

If I pray for my deceased dad and he’s already in Heaven, one of two things will happen.

The first possibility is that God, being outside time, will apply the prayer for my dad at some earlier time to help Dad get to heaven. Padre Pio did this with his deceased relatives; at one point he was praying for the happy death of his great-grandfather, who had died many decades earlier, and Padre Pio explained that God had no past and no future and would apply the prayers at the right time. I personally believe that at this point, both of my deceased parents are in Heaven, as I have prayed over this and received an answer from God via a saint, but I still pray for both of their souls and allow God to apply the prayers at the right time.

The second possibility is that if someone is truly not in need of the prayer or indulgence - let’s say that my combined prayers over time for my parents’ souls have exceeded the amount needed to help them get to Heaven even if God applies the prayers in the past - then God will simply apply it to another poor soul in need, of his choice. Sometimes I ask him to apply the prayer to another family member or to someone else in a similar position, other times I just leave it to him to choose or ask him to just give it to a soul most in need or a soul who has no one to pray for them. I trust God to do what’s best with my prayers, and this would include indulgences I obtain, Masses I request etc.
 
I think that before the Rev Mr Luther’s intervention you would get a receipt.
 
It is called an “indulgence” because it indulges (acknowledges and compensates for) our human weakness. Confession objectively wipes away all sin, and the Eucharist perfects our relationship with Christ. The two sacraments do the bulk of the work; it is thus within the church’s discretion to “bind and loose” to unbind the penalties in purgatory those filled with sacramental grace.
 
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