How much do/should children "start again" with a new teacher?

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DS1 has just gone into Yr5.

He is a very able reader (school assessed reading age 13) but has hypermobility in his fingers which means he finds writing difficult, so doesn't produce much written work.

Every year, when he starts with a new teacher, it seems to take 2 terms before they decide he's actually quite bright.

I saw his teacher after Easter and a plan was put in place to help him write and also to demonstrate his general intelligence, but she left in July and we seem to be back at square one.

I really don't want to appear pushy, but I'm starting to think I've let him down previously by not being pushy enough.

Does he have an IEP ? If not you need to see the SENCO asap, preferably with the teacher, and ask that the same plan is incorporated into one so that there is more continuity. I have a ds with similar issues and it does take time to educate new teachers as to his problems and their impact, otherwise they just see a reasonably bright, well behaved and undemanding child who gets overshadowed by the more boisterous self confident ones. Fortunately this year most have taught him before so are on board with laptop/writing slope use etc.