Redeeming one who caused himself to enter captivity:[1]

One who sold himself to idolaters, or owed them money and was taken captive as collateral, may be redeemed [using community and charity funds] the first two times that this occurs. However, if he does so for a third time, then we do not redeem him [nor his children who were taken with him] unless his life is in danger in which case there is no limitation as to the amount of times that he is to be redeemed. After the father passes away, then his children who were taken with him into captivity are to be redeemed.[2] [However, so long as the father is still alive, then from the third time and onwards we do not redeem the children[3] unless the father has no control over their Jewish education, and hence redeeming the children will save them from assimilation.[4]]

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[1] Michaber Y.D. 252:6; Rambam Matanos Aniyim 8:13; Mishneh Gittin 46b and Gemara 47a

[2] The reason: The reason for this is because we do not want the children to become assimilated amongst the Gentiles. [Shach ibid]

[3] Implication of Michaber ibid; Shach 252:6; Rashi Gittin 47

The reason: The reason for this is because so long as the father is alive and has control over his children’s education, there is no worry of assimilation, and hence no reason to exclude them from the restriction against redeeming after the third time. [Shach ibid; Rashi ibid]

[4] Shach 252:6