A devastating loss of digitized possessions, due to an unexpected and sudden malfunction of a back-up storage device (Time Machine) evokes a complex set of emotional reactions and inquiries into the nature of digital loss. This autoethnographic narrative reveals, through a reverse chronological order (to emulate Time Machine's archival data storage process), how the events followed by the loss impacted my beliefs and attitudes toward the realms of digital technology in our lives, as it relates to a habit and need for archiving and preserving digitalized possessions, both personal and professional.

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