Actually, @doschicos, I was one of those dorm parents that did a walk-through VERY late on the nights I was on duty… by the middle of fall semester I had a closet full of confiscated video games and cell phones. I was even known to take the light bulb from the desk lamps when kids stayed up way past lights out, even to do homework. (The upperclassmen with a work overload or a big assignment due could always request in advance “late lights” until midnight or 1 AM.) Generally, teenagers need decent sleep, and their very busy BS schedules do not allow much time for them to crash in their dorm rooms after classes… except for occasional free periods. After classes it is usually sports practice, dinner, study hall… My experience was that a kid who is a night owl and stays up very late at school on a regular basis is going to struggle with some effects of sleep deprivation pretty quickly.
@MA2012 is correct. Berkshire School has a terrific academic support program.
@cameo43 Did you find that most dorm parents were as diligent as you, willing to give up their sleep in the wee hours of the morning when they have their own young families to attend to? I do think there are exceptions like you but I don’t think your dedication to your in loco parentis role at that hour is the norm. I think you are the ideal, giving dorm parent that most parents wish their child to have. My siblings and I were BS kids ourselves as were my kids (several different schools) and my comments are based on those experiences.
@cameo43 that is fantastic! I love it. What school?
@KinestheticKT, I am also looking for schools that are not sink or swim, because my 7th-grade son is the absent-minded professor type. He has been working on his executive functioning skills with a teacher, a school counselor, and me. I strongly recommend the book “Smart but Scattered” by Peg Dawson for anyone whose smart child struggles with being organized, time management, following through on tasks, etc… After reading this book, I believe that time management is so much more than being disciplined about bed time, video games, etc. Of course, discipline is extremely important, but even when my son was disciplined about his time, he still couldn’t get the hang of how to properly plan and prioritize.
My son and I have started working through some of his weaknesses we identified in the book. His grades have improved significantly. His teacher and school counselor have been teaching him how to study. I have been working with him on organization. I had a huge desktop planner like ChoatieMom, but that didn’t work for my son. (Sigh. I love those big desktop calendars!) He’d forget what was written in the planner by time he got to school. After trying a few different planners, he and I created our own. This has helped him significantly. Our family also has a family calendar we maintain online. My son also struggled with misplacing school work. Now, instead of having one folder for each subject, he has a huge binder with dividers. Each time we come up with processes to keep him stay organized, I start with helping him out a lot with adjusting to the process. After a little time, he becomes responsible for the process himself. I’m not saying what we are doing will work for you, but I do think the book I mentioned will help you come up with your own solutions.
I hope you and I can keep in touch and share insights about schools that would be good for our kids. Maybe they can even go to the same school and help each other keep track of their stuff. 
Can’t really answer that one, @doschicos… On the nights that I wasn’t the dorm parent on duty, I usually went to bed early. It seemed that when I didn’t do my late-night patrol, that was when things would inevitably “happen”… all sorts of nutty hijinks in a house of 50 boys.
Smells indeed. I really sympathize with anyone who lives with 50 boys.
@cameo43 oops ok. :"> :-S
@PossiblePrepMom I will PM you. Sounds like an interesting read.
You might want to check out the book “That crumpled paper was due last week” – it has some good strategies in it for getting organized and also does a good job of providing reasons (compelling to kids) for soing so. It also recognizes the various forms that disorganization can take. (Ugh, I recognized myself in one of them!)
In so many ways, BS is such a gentle path to independence. At college, there’s no @cameo43 wandering the halls at night, and college advisors tend to be interested primarily in academics. It’s nice that kids have the safety net they do at BS, but it is a big transition from home. While there are a million ways to avoid the rules (especially lights out), it’s probably better for most kids to have to break the rules than to not have them at all…These are really important things to check out!
@gardenstategal thanks! I’m sure if we are honest we all can find areas to improve in some skills be time management or some other competency.
On the OP’s question: Mercersburg has supervised study hall for 9th graders (good grades get them out of it after a while) and briefly for new 10th graders.
My kid who is a sophomore at cate now had a reputation for being very disorganized and not much of a planner AT ALL and would pride herself on living in the moment which sounded great but left a path of distruction in her wake. Ok. It wasn’t that bad but you get the point. No, she did not go into boarding school with time management skills but that’s no reason to leave a child out of this amazing opportunity. They mature, they look around at all these other put together people, and they figure out how to adapt for survival and gain a tool or two along the way. In just this short time, my daughter has figured out how to manage and even enjoy her academic environment even though she didn’t start out prepared. Prep school isn’t always short for preppy…
Btw: I think I posted the exact same question two years ago. Unless they are at a school that really is not the right fit, they will adapt. If they don’t, you’ll know.
@freshlook , I’d guess that Cate recognized in her both the desire to succeed and the ability to do what was required even if that wasn’t immediately evident on day 1. That’s the “fit” thing we all hope is right. It often is, but not always.
@freshlook I’m sure your daughter had great qualities that developed into even more at Cate. D2 has made it clear she does not want to go too far, but did look at Cate. Though I know we have some time, I’m hoping we can get around to visit her choices and for her to find her fit.
It was arrival day at Thacher. Incoming freshman are paired with a senior who walks them (and parents) to the dorm room, helps with where to park the car, helps carry stuff, and answers all those last minute questions that crop up. By chance, my son got paired with the student president that year. What a great guy he was. He told my son, without being asked, that the one piece of time management advice he’d give to any freshman was to use free periods during the day to get as much homework done as possible. However obvious that little bit of advice may be, hearing it delivered in person on day one by a senior made it stick. And, in fact, it was one of the best time management messages ever, and became a discipline my son adopted to his great advantage.