This screams dysgraphia or dyslexia to me.
You might try these instead of sitting with pencil and paper:
trace letters on fine sandpaper
trace letters in the air using big, wide, sweeping motions (engages major muscles instead of fine motor)
trace letters on an iPad or draw them in a drawing app
These helped tremendously, but mostly it just took time. His writing was basically illegible until fourth or fifth grade when his motor development caught up a bit. Physical therapy helped tremendously.
Thank you. I am going to incorporate some of this into his writing I think. He dislikes the handwriting app I have that has HWT letters in it, but maybe I can encourage just one letter with the handwriting we do, plus a sensory or larger motor use. PT we considered, but without a diagnosis it's hard to get covered. We may revisit with a different PT as the last I don't think was very specialized (but was a peds PT experienced). We have a large clinic affiliated with a national children's hospital within driving distance so we may try that. There's also a local speech therapist who I think has a PT come in and they advertise writing help so I may look into that, even if we have to pay out of pocket.
