I did some additional testing on a fresh install.

1. ~/.thumbnails and ~/.cache/thumbnails do not exist.
2. Open existing images with ristretto, no thumbnails, no thumbnails generated.
3. Open existing images with thunar, thumbnails are generated.
4. Open new images with ristretto, no thumbnails are generated.
5. Manually create ~/.thumbnails
6. Open new images with ristretto, no thumnbnails are generated in either 
directory.

Based on this, I can conclude that thumbnail generation is not happening
in ristretto.

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https://bugs.launchpad.net/bugs/1756191

Title:
  Thumbnail sidebar shows error icons in place of some images.

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