This is similar to {T57767: VisualEditor: Adding an image at the top of a list puts the image inside the list}.

Start with a section whose contents are:

==Heading==
; Alice
: Bob

Drag an image to the space in between the ==Heading== and ;Alice.

The image will be placed inside the list:

==Heading==
; [[File:Example.jpg]]Alice
: Bob

This is rendered 'broken' upon saving. However, the display that the editor sees in VisualEditor is what the editor (probably) wanted and expected. The desired output is:

==Heading==
[[File:Example.jpg]]
; Alice
: Bob

See https://en.wikipedia.org/w/index.php?diff=684818438&oldid=684818277 for an example. This edit was done in Firefox 41 on Mac OS 10.10.5.