Commentary for Kiddushin 43:4
אמר בסוף שש ולא אמר בתחילת שש אינו נרצע שנאמר אם אמר יאמר העבד עד שיאמר כשהוא עבד
but not at the end, he is not bored, for it says.' I will not go out free': [hence] he must say it when about to depart. If he says it at the end of the six[th year], but not at the beginning, he is not bored, for it is said: 'But If the slave shall plainly say': he must say it while still a s
Daf Shevui to Kiddushin
The baraita teaches that the slave must twice make the declaration that he wants to remain a slave—at the beginning of his term of servitude and at the end. We will see below how later rabbis interpret this. It seems somewhat absurd that the slave should have to make this statement at the beginning of his term of servitude.
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