I've noticed that too, once you get an initial implementation it seems to always find a way to argue for keeping that approach in the name of simplicity

Like "Let's stick with what we have, its simple and it works." or "That seems overkill, let's not over complicate things"

In this vein, I have a system level memory for Claude to push back and give me direct feedback when possible. So far a success as it helps cut through the sycophancy.