3,530. Acting Cleverly When Redeeming Second Tithe

Hilchos Maaser Sheini and Neta Revai 5:8

One is permitted to act cleverly when it comes to redeeming second tithe. For example, one may give money to his grown son or daughter or to his Jewish servant with instructions to redeem the produce, obviating the need for him to to add a fifth. However, he may not give them money and tell them to redeem it for him. Likewise, he need not add a fifth if he tells them to redeem it for him using their own money.

Hilchos Maaser Sheini and Neta Revai 5:9

One may not give money to redeem second tithe to a minor son or daughter or to a Canaanite servant because they lack legal independence. If he gave money to his Jewish maidservant, his instructions are effective when the produce is second tithe rabbinically, such as if it was grown in an unperforated flowerpot. This is because a Jewish maidservant is a minor, and minors can acquire property for others when it comes to rabbinic obligations.