Most of the software I use doesn't need to refer it itself in the first person. Pretending what we're speaking with an agent is more of a UX/marketing decision rather than a technical/logical constraint.
It isn't an experiment I have the resources or the knowledge to run, but I hope someone does and reports the results.
Command prompts don't get asked questions like "What do you think about [topic]?" and have to generate a response based on their study of human-written texts.
E.g. 'File not found' vs 'Sorry I could not find the file you were looking for.' Same stuff, but one just adds an artificial and unnecessary anthropomorphization.
In your example:
-- "iteration over filenames table reaches end → file not found";
-- "non-deterministic choice over lookup strategy does not return a positive → sorry I could not find the item"
It anthropromorphizes itself.