I tried importing my WordpressDotCom website into Jekyll, but I had 350 images get lost/overwritten. This was due to the authoring tool I was using naming all images: image1, image2, image3.
e.g.

/2020
  /01
    image1.jpg
    image2.jpg
    image3.jpg
  /02
    image1.jpg
    image2.jpg
    image3.jpg

but the WordpressDotCom importer, puts all images into /assets which results in them overwriting each other.

I see that there is a similar issue from 6 years ago that went stale #173