Counterpoint - almost all jobs will have elements of this type of stressful fuckery. Use it as a learning experience, and do your best to navigate the constraints while maintaining professionalism and value to your employer.

It's a balance; if it's truly soul destroying then your health and happiness is more important, get out. However, the more you learn how to deal with this, the less likely you are to burn out in other jobs when they get shit like this. Not so that you can just suck it up and grind away for awful bosses, but so that you can give yourself the maximum options for you, and stress less while going through it.

You already seem to have the right mindset about trying to do this right, so the one thing I'll say is this: everything in writing, straight away. It's easy to get too relaxed about this when it's all going smoothly, but then something catches you out and it's too late (eg already been told not to bring it up again).

This part will feel awkward, but to protect yourself, you need to send your boss an email summarising your conversation and your understanding of the outcome (not updating). Frame it as a "I hear you, and I apologise for my previous insistence" if it helps smooth things over, but just make sure it outlines your previous queries and suggestions and their response to you. It's the only way to cover your own butt in these situations, and it's a great habit to get into after every conversation that has decisions or changes etc. Put it in writing as a summary: you can refer back to it later and it let's the other person know you understood their position / instruction