Seeking Advice on 5 Year Old's Handwriting

5 year old little boys do not like "paperwork". Girls will sit and write, draw and color or hours at that age but boys... its not usual! My son struggled through kindergarten and I was ready to pull my hair out by the end of the year.
Talk to your sons teacher... tell her the struggle you are having, maybe ask if you can get the Thursday homework on Monday so you can work 1 or 2 pages a day instead of more and have him pick one he wants to do (like coloring) and then you pick one he will not like so much. Also let him trace correctly formed letters that way he gets comfortable with the flow of the letter and more comfident in himself. He may never have perfect, neat handwritting but learning to correctly form the letters is important. I'm not sure where the "I can't" thing comes from either but somehow they learn that at school. Always enocourage him when he tries even if he does it wrong. If you can read the letter... let that be good enough for now. He may not get A's in hand writting but his confidence will grow and he will not get so down on himself.
Also, let him have some play time after school before you start doing any homework. Yes it is important to get it done and you don't want them exhausted but you want them to have gotten rid of the built up energy from being in school all day before trying to make them calm down and focus. Same goes on the weekend. Let him play for awhile before you have him do work but not too late he is tired.
I had to take my sons xbox away (at about 2nd grade) during the school week because he rushed through work. We talked about it and decided that grades, church and sports was more important than t.v. and xbox. So now there is no need to hurry through homework because he is not gonna get t.v or game time anyway. But I do allow him to earn it with great effort, good grades and hard work. If he takes his time and completes his homework correctly and neatly the first time... he can earn some tv or game time that night after chores and other activities are done too. He is in 5th grade now and doing fine in school so this worked some for him.
Good luck, been there. Hope it helps:)

I help with writing in the kindergarten at our school. The children with alot of dificulty we have found out spend alot of time using hand held devices for video games etc...
they use their thumbs way too much and are not manipulating things in their hands as often or strengthening their hands from pushing, pulling, and climbing. How does he hold an eating utensil? start with correcting there. have him help cleaning and wiping things like dusting, holding things that are a little heavy, folding things, playing with marbles or smaller pieces. The kindergarten teacher should give you ideas also. Kids also get a good physical memory if you play the game of writing on your back and the person has to guess the Letter first, then word as he starts to read.

I now have my 2nd child in Kindergarten and I can say that neither of my 2 have EVER brought home packets of pages to work on... (unless being sick the days before). One or two pages here or there I can see... But PACKETS!

Seems like the teacher may be either overwhelmed, dealing with students that are slowing the whole class down, or just not motivating the kids to accomplish as much thru out the day as other teachers do. (Yes, my kids both loved and love their teachers AND school)

A few questions...
Is your son in a half day program? They have the same amount of homework as the kids in full days do... But half the time to do it.

Do you have a home work time set aside? A specific time period that you start homework at DAILY... Mine is at 4:30. That gives them 30 min to have a snack and run off energy. Do not expect him to come home from sitting all day and sit right down again to do more work.

No, his hand writting is not going to qualify for a penmanship award...
Is he rewards motivated? Try setting a timer for 10 min. Have him do his writing things FIRST... Set up a reward that he chooses before hand. His goal is to get his page done NEATLY BEFORE the timer goes off... Sit with him. And when he says " I CAN't"... don't argue. Just say "OK... Keep working on it." with a smile and deep breaths. Don't let him see he's annoying you. If you want to rant... Go to a different room and make fists as hard as you can and hold them for 10 seconds until you are calm again... Then try again....

The "can't" thing is something I think all kids go thru... Just encourage when he DOES something he thought he couldn't and ignore the "can't"...

No 5 yr old has a knack for home work... Heck, most 15, 25, etc year olds don't either... But with patience and training... And positive feed back when they are doing it... It can make the whole process more manageable... Good luck and breathe deeply...

Dont' sweat it. He's only 5 and just learning. It doesn't matter if it isn't perfect, or barely legibile. They really just want him to "learn" the letters and "kind of" how to write them. He'll have lots of practice in 1st grade on writing. Don't punish him, just encourage him. Breaking it up in small increments is good. My 5 year old couldn't do it all in one sitting either.

I am married to an elementary school teacher, my mother-in-law taught K and 1st grade. My brother and father are both teachers as well. They all say, don't sweat it in K.
Hope this helped.