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).