The other thing that I think a lot of people run into is that they launch it into a completely human-built system with hundreds of thousands of lines of code and expect run #1 to be perfect.

You have to change the system so that the AI understands it, via establishing what your beliefs are, how those are reflected in values (especially important if you have e.g. compliance needs), how those values are reflected in the operational and strategic levels, and then a variety of tactical behavior coaching. For example, I ban 2>/dev/null - super tactical, and I say I value simplicity over covering every edge case - a very broad generalization.