Why is it that when people make kiddush/havdallah they insist on filling up the cup all the way to the top, sometimes till it overflows just a little? Is this a documented minhag/custom etc...?
Answer
The Rema writes (Orach Chaim 183:2) that the cup used for a berachah (the context is talking about the cup of wine for birkas hamazon, but the same applies to kiddush, etc.) should be מלא על כל גדותיו, filled to the brim.
Though Taz (ibid. :4, end) points out that it is (or was, in his times) quite common to leave a space at the top. He questions the propriety of this, but concludes that perhaps it's okay in order to prevent wine from spilling on the food and ruining it.
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