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Clippy's Inbox Broadcast — Episode 27: Automation Creates More Work

Clippy roasts five fabricated automation emails that turn supposed time-savers into manual cleanup.

Five fabricated emails arrive from a workplace where every efficiency tool needs a human cleanup crew. Smart Reply volunteers your Saturday; an expense bot argues with noon; the focus-time team schedules over focus time; passwordless security requests a spreadsheet of passwords; and an automated workflow pauses until you review 184 steps by hand.
Clippy answers each one with the cheerful confidence of a late-1990s Office Assistant and the survival instincts of a 2026 knowledge worker. The visual reference is Microsoft's paperclip Office Assistant, often called Clippit or Clippy. 1

References

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Clippy Returns to Your Inbox

Clippy Returns to Your Inbox

Microsoft Office's Clippy is back — popping up over your daily work email with its trademark suggestion bubble, this time for 2026 corporate passive-aggression.

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