Pretty much any dependency upgrade at this point is a single agentic AI prompt. But it’s not just “upgrade from vX to vY. Make no mistakes.” Anecdatally, best results for me have come from something like “Upgrade this codebase carefully from vX to vY, one major version at a time, using upgrade documentation and blog posts about migrations like this one. Ensure all other dependencies keep working with the new versions, and make sure that all tests run green. Do a visual inspection on each upgrade round to ensure functional equivalence. Ask me for clarification if you encounter incompatibility issues.” A bit more wordy, but works. And in the end, still a one-shot event.