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Once entered into slavery, they have a semi-conversion whereupon they must keep a certain set of limited rules. Can they choose to fully convert and then be freed at the appropriate time of Shmita and Yovel?

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    An eved kna'ani finishes his conversion by being released. There's nothing else to do but wait.
    – Double AA ♦
    Dec 21, 2016 at 5:17
  • is there not tevila leshem shichrur (yebamot 47b) בד"א שלא קבלה עליה אבל קבלה עליה מטבילה ומותר בה מיד ר"ש בן אלעזר אומר אע"פ שלא קבלה עליה כופה ומטבילה לשם שפחות וחוזר ומטבילה לשם שחרור ומשחררה this is the view of Rabbi Shim'on Ben El'azar, but it seems that tevila is needed for every opinion
    – kouty
    Dec 21, 2016 at 8:19

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They might be able to fully convert at the original time. Once they have entered into slavery, however, all the laws of עבד כנעני apply. They cannot escape that status voluntarily.

In any case, no slave regains his freedom at Shmita. All slaves (except a Canaanite) regain their freedom at Yovel, but the only ones whose freedom is bound only to Yovel is (a) the עבד נרצע, a Jewish manservant whose six years (not Shmita!) have expired but chooses to remain by having his ear punctured, and (b) the נמכר לעכום, one who has sold himself to a non-Jew. (Actually, the latter can also buy his freedom, either himself or through a relative.)

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    sources would greatly improve this answer
    – ezra
    Dec 21, 2016 at 20:31

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