When one loses a family member it is customary to recite mourner’s kaddish to elevate their souls during the year of their passing. An interesting question can arrise to those that are involved in kiruv. A child who was not-yet observant lost a parent and did not recite kaddish during the year of mourning. Years later he becomes observant and now wishes to recite kaddish for a year in order to “make up” for the kaddish prayers he did not recite during the year after their passing. Is this permitted to be done or is there a halachic problem involved.

Section 1: The View Not To Recite Kaddish
The reason to prohibit reciting kaddish in this instance is based upon a teaching of the Rama (Y.D. 376:4) who explains that the Talmudic Sages teach that the maximum that a very wicked person is punished in the afterlife in gehinom is 12 months. The public recitation of kaddish shields the departed soul from this punishment. Hence, kaddish is recited during the first year after a parent’s passing. However, the custom is to recite kaddish for 11 months only. Saying kaddish the entire 12 months would give the impression that the deceased was a very wicked person who needs protection the entire 12 months.
If reciting kaddish during the twelfth month is avoided because it gives off the impression that the parent was wicked and is still being punished. All the more so that reciting the kaddish years later would imply that the parent is still in need of protection from punishment and should be prohibited.
Indeed, Rav Avraham Yitzchak Hakohen Kook zt”l (Shu”t Daas Cohen 217) was asked regarding a child saying kaddish in the instance where, due to confusion, it is unclear whether the child is currently in the tenth month after the parent’s passing or in the twelfth. He rules that the child should not do so, since there is a possibility that he is in the twelfth month it would be inappropriate to recite kaddish. It would be safe to assume that in our situation, Rav kook would advise against reciting kaddish.

Section 2: The View To Recite Kaddish
Rav Yaakov Hillel shlit”a (Vayeishev Hayam 1:18) discusses this very question and he maintains that one should recite kaddish and that it is based upon the teachings of the Ari z”l.
The Ari z”l explains that Kaddish helps the departed not just to alleviate the punishment of Gehinnom, but also to elevate the soul in Gan Eden. It is for this reason that we recite kaddish on Shabbos and Yom Tov, despite the fact that all souls receive a respite from Gehinnom on Shabbos and Yom Tov.
The Ari z”l disagrees with the Rama and maintains that kaddish should be said in the twelfth month as well. This can be easily understood with the fact that the Ari z”l feels that kaddish is meant to not only alleviate the soul from the punishments of Gehinnom but to elevate the soul in Gan Eden. The Chida cites the view of the Ari z”l and writes that many recite kaddish into the twelfth month, but only refrain from the doing so the last week of the year of mourning.
Previously, we cited the Talmudic Sages who teach that the maximum that a very wicked person is punished in the afterlife in gehinom is twelve months. However, according to the Ari z”l not everyone goes to gehinom immediately after one passes. There are evil people that are not worthy of beginning the “cleanse” of gehinnom right away. And it would be possible for one’s year of punishment to begin time after the person’s passing. Refer to Hebrew footnotes for further elaboration of this view.
Based upon the above views of the Ari z”l, Harav Yaakov Hillel shlit”a maintains that in our situation one should recite Kaddish for his parent, despite the fact that it has been years since the passing. One should not worry that it gives off the impression that the parent was wicked and is still being punished since kaddish is effective in elevating the soul once it is peaceful in Gan Eden. In addition, it is possible that the twelve months of Gehinnom began years after the passing and soul is currently in gehinnom and in need of protection. A similar ruling was given to the author by Hagaon Rav Yitzchak Meir Morgenstern shlit”a.

Conclusion of the Poskim
The poskim address the following halachic question. A child who was not-yet observant lost a parent and did not recite kaddish during the year of mourning. Years later he becomes observant and now wishes to recite kaddish for a year in order to “make up” for the kaddish prayers he did not recite during the year after their passing.
Some poskim prohibit the recitation of kaddish based upon a teaching of the Rama who explains that the Talmudic Sages teach that the maximum that a very wicked person is punished in the afterlife in gehinom is 12 months. The public recitation of kaddish shields the departed soul from this punishment. Hence, kaddish is recited during the first year after a parent’s passing. However, the custom is to recite kaddish for 11 months only. Saying kaddish the entire 12 months would give the impression that the deceased was a very wicked person who needs protection the entire 12 months.
Rav Avraham Yitzchak Hakohen Kook zt”l was asked regarding a child saying kaddish in the instance where, due to confusion, it is unclear whether the child is currently in the tenth month after the parent’s passing or in the twelth. He rules that the child should not do so, since there is a possability that he is in the twelth month it would be inappropriate to recite kaddish. It would be safe to assume that in our situation, Rav kook would advise against reciting kaddish. A similar restrictive view can be found in the sefer Shvus Yaakov (2:39).
However, Rav Yaakov Hillel shlit”a maintains that kaddish should be recited and one need not worry that it gives off the impression that the parent was wicked and is still being punished. He bases this on the teaching of the Ari z”l that kaddish is effective in elevating the soul even once it is peaceful in Gan Eden. A similar ruling was given to the author by Hagaon Rav Yitzchak Meir Morgenstern shlit”a. For practical halacha, a rabbi should be consulted.

Those that are involved in kiruv give their hearts and souls to help other Jews become closer to Hashem. They exert every effort to help them do teshuva and become more observant. A very important tool in helping other Jews is prayer. To pray to Hashem that they become closer to Him.

This is evident from a story related in the Gemara (Brachos 10a). The Gemara says, “There were these hooligans in Rabbi Meir’s neighborhood who caused him a great deal of anguish. Rabbi Meir prayed for God to have mercy on them, that they should die. Rabbi Meir’s wife, Berurya, said to him: What is your thinking? On what basis do you pray for the death of these hooligans? Do you base yourself on the verse, as it is written: “Let sins cease from the land” (Psalms 104:35), which you interpret to mean that the world would be better if the wicked were destroyed? But is it written, let sinners cease?” It is written ‘Let sins cease’. Rather, one should pray for an end to their transgressions, not for the demise of the transgressors themselves.” It seems clear from the Gemara that one may pray that someone else should repent. Which is also indicated by the Zohar (Medrash Neelam Vayeira). Yet, after analyzing the commentaries this may not be as clear as we shall discuss in this chapter.

The Question of the Maharsha
The Maharsha on this very Gemara, raises a fundamental question: How can anyone pray that someone else should repent? Does this not violate the principle of free choice that “all is in the hands of Heaven except for fear of Heaven” (Brachos 33b), meaning that Hashem does not predetermine or otherwise interfere with a person’s free choice? The Maharsha explains that it is one thing to pray for Hashem to help one’s own effort to repent, as we do in shemoneh esrei, since that is using your free choice to ask for assistance. Therefore, any spiritual improvements that results can be attributed to the person’s own free will rather than to an act of God. But when it comes to praying for someone else, this explanation does not suffice. The Maharsha does not answer the question. It would seem that he would practically not advise praying for others to do teshuva.
The Chazon Ish (O.C. Hashmatos 156) maintains that there is no difference between praying for one’s own spiritual improvement and that of another Jew. Just as praying for help in one’s own moral struggles is appropriate because the person himself is making the free-willed choice to do whatever possible to come closer to Hashem, so too, is praying on behalf of someone else. Since all Jews are responsible for one another and are thus like one person. When one prays for another Jew it is he who initiated this process and is therefore not an interference in our free will, but rather a result of our free will.
Rav Efraim Greenblatt zt”l, the author of Rivevos Efraim and a student of Rav Moshe Feinstein zt”l, offered a similar view to that of the Chazon Ish and Rav Moshe (Igros Moshe O.C. 4:40:13) rejected it and maintains that it is not satisfying. Rav Moshe agrees with the Maharsha that one may not pray for one to do teshuva. How then could Rav Meir pray for the sinners to stop sinning? Rav Moshe explains that often times one sins due to their circumstances. For example, there are people that would like to keep Shabbos but find it difficult to do so because they are in need of money and there is a temptation of parnassah etc. One may pray, argues Rav Moshe, for Hashem to send them wealth in a permissible way, removing the temptation of money. This was the case with Rav Meir. According to Rav Moshe one may not pray for someone to become closer to Hashem, however, you can pray for their physical circumstances to change in the hope that this will lead them to choose on their own to come closer to Hashem.

Summary and Conclusion
A very important tool in helping other Jews become more observant is prayer. To pray to Hashem that they become closer to Him. This is evidenced from the story og the Gemara where Rav Meir prayed for sinners in his community to repent. However, the Maharsha feels that this is improper as this violates the rules of free choice. Namely that Hashem will not interfere in another’s life in order to cause them to become more observant. Rav Moshe Feinstein zt”l agrees with the view of the Maharsha. According to Rav Moshe one may not pray for someone to become closer to Hashem, however, you can pray for their physical circumstances to change in the hope that this will lead them to choose on their own to come closer to Hashem. The Chazon Ish disagrees with the Maharsha and he feels that one is permitted and even recommended to pray for others to become more observant.