WW doesn't want to discourage you in any manner from eating veggies... and therefore doesn't tell you to start counting points if you eat more than a serving of green beans. So don't worry about eating more than a serving of 0-points vegetables.
For everything else - light cool whip, fiber one cereal, jello, etc - you should look at the nutritional information if you are going to eat more than one serving. If you eat two servings of cool whip, for example, double the nutritional info, and figure out points on those numbers. Do that for each subsequent serving. Sometimes it'll jump - zero for one serving, one point for two servings, three points for three - which is why it's good to get in the habit of always checking the nutritional info.
It's a pretty big grey area. We discussed this at meetings a few weeks ago and it seems the official WW decree is that you look at your weight loss. If you are losing just fine, don't change a thing! However, if your losses are slowing or stalling, take a look at the 0 foods you eat and see if you aren't fudging the numbers a bit.
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