I have project folders/files and memory stored for each session, when I come back to my projects the context is drawn from the memory files and the status that were saved in my project md files.
Create a better workflow for your self and your teams and do it the right way. Quick expect the prompt to store everything for you.
For the Claude team. If you havent already, I'd recommend you create some best practices for people that don't know any better, otherwise people are going to expect things to be a certain way and its going to cause a lot of friction when people cant do what the expect to be able to do.