For me, the decision to "give someone a grace period" would be contingent upon whether or not the late pick up was a regular occurance or not. My current parents are all very respectful of my time. If they know that they are going to need a couple of extra minutes at the end of their day, they tell me (usually at morning drop off) and I am able to accomodate. IMO though, this is very different than the sort of client who shows up 15 minutes late with no explanation, no apology, and frankly, no respect for my personal time. I wouldn't be inclined to charge a late fee if they're just a minute or two late (traffic happens, snowplows are out there) but....I would keep an eye on things. If they are late by more than 10 minutes - feel guilt free about charging them the penalty. I would also consider sending out a note to this parent reminding them about the importance of picking up their child on time, and reminding them that their children are expecting them to arrive. I have a little one who even though she can't tell time, she "knows" when it's around pick up time, and if her Mum is late - she gets quite anxious. If you notice that they are continually late by "just a few minutes" give some thought to telling the problem family (in writing) that you are changing your hours. The new closing time for the late family is half an hour earlier (i.e. 4:30) than the parents who understand 5 o'clock means 5 o'clock. I did this with a couple of my first clients who weren't terribly good at telling time.