The Jewish Legal System: Business Law: A Slave Refusing to Go Free:
Can a slave refuse to go free?
When the Jubilee year comes, or his owner dies, the slave no longer belongs to anyone (Mishneh Torah, Hilchos Avadim 3:7); thus he automatically goes free, even if he doesn't want to. But he can always sell himself again if he has no resources (see 1:1); and if he chooses to sell himself to the previous owner or his heirs, the effect would be tantamount to "refusing to go free".
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