That "hard reset" feeling is spot on, it really breaks the flow. I've hit the same wall when trying to draft customer onboarding checklists. The model will agree to use our specific template format, then a few messages later it's generating a generic bulleted list.
> I'm currently just dumping everything into a single, massive initial prompt
I do this too as a last resort, but it feels so clunky. I've started a little cheat sheet for myself - a "session primer" text file with the absolute non-negotiable constraints. Before I ask a new, related question, I'll just paste a one-line reminder like "Please continue using the Airflow/Snowflake setup from our initial spec." It's not perfect, but it seems to help the model latch back onto the right thread without retyping everything. Have you tried anything similar, or does it just feel like extra overhead?