My son is 5.5, and we’ve started kindergarten this year. I tried working with him quite a bit on his pencil grip when we started at the beginning of the school year, and it left him frustrated, so I did the best I could and left it at that. Currently, he uses what I call his ‘pincher fingers’ (thumb and index finger) to ‘pinch’ his pencil, which is a good start, but then he won’t put the rest of his fingers to rest behind his pencil. He bunches them all together on his pencil. We tried using the rubber pencil grips, and that didn’t help, he was really uncomfortable. He does use one of the bigger sized pencils. I’ve tried holding a pencil like he does and it seems really uncomfortable, nor is it the way he’s ‘supposed’ to hold it. Should I be concerned? Am I overanalyzing? :o) Will he eventually get it?
I don’t know if you should be concerned or not. But what has worked for my 5.5 year old is a molded pencil grip, it has a spot for her thumb, index and middle finger in the correct spot. You could also try a triangle pencil or triangle pencil grip.
I would work on correcting it how. I am trying to correct a grip in my 7 yr old that is causing problems with her writing and art (she only cares because it is impacting her art and writing stories more now). She used to use a different grip, but somewhere changed along the way and it is very difficult to overcome. Depending on the grip, it can be problems with hand stability and/or shoulder stability. The OT Mom blog has ideas of exercises for strengthening each. I have the pencil gymnastics kit from The handwriting Clinic to try and strengthen and help remediate her grip. I only require her to try and use a proper grip right now while we are specifically working on handwriting.
You can keep working on it here and there, but I wouldn’t turn it into a major thing that he stresses over. It’s a skill and motor skill kids acquire over time. He’ll get it over time… may not be YOUR way, or the way shown in books, but he’ll eventually do what is comfortable for him. Honestly, he’s not going to go to college without the ability to hold a pencil and write 
I would just take your time with it…it sounds like you are aware, doing the right things to help. My lefty son had a terrible grip. (I am a righty…yes, cursive was FUN to teach!! 
) Anyway, we used the triangle grips and the soft rubbery grips in Kindergarten to get him to change his hold. It’s fun to get crazy colors to add to the interest. Now a teenager, his grip is still different than mine, way improved over his 5 year old grip, but it is his grip, his printing is very neat, and he does not complain about hand pain at all. The key for me was to release “MY GRIP” a bit and encourage more…if you know what I mean.
Thanks for all the tips! I think I’ll give the rubber grips I’ve got another try, but if he just can’t seem to catch on, try again later and if he’s comfortable with how he’s writing, I’ll just leave it be :o)
We use BIC kids mechanical pencils. They have a yellow piece on them for correct placement. 
We have it in pink and blue. They also have kids pens. You might want to check them out on amazon.
I bought our first one on clearance at Kmart after school started. Then I picked up the blue one at staples. They come with extra lead and a long eraser.
Also the lead is 1.3 mm. And lasts so much longer than a regular pencil. That is why we bought one. I was tired of sharpening a ton of pencils:)
I would definitely encourage teaching correct grip early on. My nine year old recently underwent weekly handwriting therapy for almost 2.5 months to correct an awful pencil grip.
If you haven’t used/heard of Handwriting Without Tears(hwtears.com) I highly recommend it!
Something that I have learned from an Occupational Therapist at a handwriting training is that big pencils are a big “no-no”…lol! Instead young children (K-1) should use golf pencils. You can purchase them at the HWT website, but I ordered ours from Amazon click here for the link
As for my 9 year old, his handwriting has dramatically improved and no more funky grip! The handwriting therapist did all that without the aid of any type of gripper on his pencil. She did recommend three sided pencils(so that he has space to put each finger holding the pencil. I also ordered these on Amazon tri write pencils