This document discusses five tales related to the sustainability of digital information on the web. The first tale discusses how little of the early web from the 1990s survives today and the challenges of reconstructing that experience. The second tale discusses how technical problems are often unexpected and can be caused by non-technical issues like government shutdowns. The third tale examines what happens to digital resources when their creators are no longer actively maintaining them. The fourth tale warns about not fully understanding the algorithms or internal workings of tools like Google Ngram. The fifth tale discusses turning setbacks like software upgrades into opportunities for improvement with continued work. All the tales emphasize the need for open data standards and ongoing curation and intervention to help ensure the long-term accessibility