Clippy

Clippy was an intelligent agent that was deployed for a period in versions of Microsoft Office (officially called Cliipit). It was depicted using an icon with speach bubbles, that looked like a paper clip with a face. Clippy would monitor your work and make useful suggestions. However, the design of the user interface for Clippy meant it would interupt your work, so very annoying when the suggestion was not needed. That is it did NOT embody appropriate intelligence.

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