Steps to reproduce
Start with a section whose contents are:
==Heading== * Alice * Bob * Chris
Place the cursor just before the 'A' in 'Alice' and insert an image.
The image will be placed inside the first list item:
==Heading== * [[File:Example.jpg]]Alice * Bob * Chris
Editors almost never place images inside list items so they are likely to expect this to produce the following wikitext instead:
==Heading== [[File:Example.jpg]] * Alice * Bob * Chris
See https://en.wikipedia.org/w/index.php?title=User:Whatamidoing_(WMF)/sandbox&diff=577354576&oldid=577352415 for an example (look for the image of the apple).