Chip cards require you to enter a PIN instead of signing. I'm not sure what the case is with low dollar value transactions (you might notice that you no longer need to sign for credit card transactions at some retailers such as fast food, etc, if the total transaction is under a certain amount), but the proper procedure is to insert the card with the chip, enter your PIN, and then remove the card when prompted to do so (after authorization is received).
Visa's instructions:
http://www.visa.ca/chip/cardholders/howtouseachipcard/
That being said, I used a chip credit card as the machines at Waterfront would not accept my debit card and it did not prompt me to enter my PIN. The credit card still has a magstripe though, so I'm not sure if the transaction was processed through the chip or through the magstripe. My regular magstripe-only credit card wouldn't work either and an attendant was nowhere ot be found.
