We had similar issues with my 5th grade son (he has handwriting difficulties and ADD). Our struggle was in actually getting him to remember to write in the book at all. I asked his teachers to help encourage him to write something, anything, in the book at the beginning of his class, just to get in the habit of writing in it. He surprised me that first day and wrote down every assignment for every class! It worked for a little while, and eventually I had to remind him daily before and after school to remember his assignment book. What was confusing to me was: the teachers ordered a specific assignment book for each student, and then they didn't train the students to use the assignment books. It was like the kids were just supposed to instinctively know how to use them. Whatever.

As for your issues, I have some ideas and suggestions. They are all untested by me, but I am just throwing them out there.

Use a small handheld tape or digital voice recorder to record his assignments, then at home he and/or you can transcribe them into his assignment book. This might work well if he is into tech gadgets.

Have each assignment pre-written or pre-typed on one self-stick label (or even a Post-it note) that fits into the assignment book. The teacher can keep the labels in a specific spot in the classroom, and he can peel and stick the appropriate assignment for the appropriate day in the assignment book.

Have a helper student act as a scribe and when he/she writes down his/her assignments, he/she can write your son's down in his assignment book as well. (I don't like this idea so much, but it might work for you.)

Use a free online calendar, like Google's Calendar, to record each assignment in the appropriate day. Google Calendar has lots of space to keep notes in each calendar entry. Our family actually uses this application a lot, but not for school assignments.

Hope this helps!

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My daughter just finished fourth grade and she has struggled with handwriting for some time. She was tested last year (while in 3rd grade) and diagnosed with dysgraphia. We did not include the daily assignment book in her accommodations, mainly because it never occurred to me. She doesn't have any problem writing it, but she is the only one who can read it! I think if your son's issues are this difficult, you might seek testing for dysgraphia so that you can get a 504 plan which will make everything official. We have not had any problems getting accommodations form her teachers but I hear of so many others who have to fight the school for everything so it is best to have it in writing if at all possible. The accommodations we have are - she may type long assignments, she can have a scribe for timed tests (particularly for the standardized testing that determines our school's funding), and she can have a scribe for homework.

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