https://bugzilla.wikimedia.org/show_bug.cgi?id=69205

            Bug ID: 69205
           Summary: Creating numbered lists with images resets the
                    numbering back to 1 for each list item
           Product: VisualEditor
           Version: unspecified
          Hardware: All
                OS: All
            Status: UNCONFIRMED
          Severity: major
          Priority: Unprioritized
         Component: ContentEditable
          Assignee: [email protected]
          Reporter: [email protected]
                CC: [email protected], [email protected],
                    [email protected]
       Web browser: ---
   Mobile Platform: ---

Since I have multiple screenshots (6), I've placed them in an Imgur album:
http://imgur.com/a/emySl

1) User creates a numbered list as instructions on how to install a piece of
software in a IT Documentation Wiki. They use the button in the toolbar to
create this numbered list.
2) They create list item 1, 2, 3, and 4 WITHOUT any screenshots JUST text. (See
bug screenshot 1)
3) User places cursor at the end of each line to add a corresponding screenshot
for what's described in the text of that line.
3) They use the "Insert media" dropdown, search and select their image, and
place it with their cursor directly at the end of the line. This places the
image on the next line.
4) They go into the properties of the image and uncheck "wrap content with this
item" and select "basic" as the image type. This places the image at original
size left aligned and directly below the line it was placed on (This is correct
and normal).
4) They repeat this for each line and it appears correctly with correct
numbering in tact. (See bug screenshot 2)
5) They save the page. 
6) Once VE is closed out and the final render of the page appears, each
numbered list is reset to 1, and the images are now not aligned with the list
indenting. (see bug screenshot 3)

I've found a work around however it's not very convenient:

1) If a user then goes into the "edit source" page for that page, they will see
each list item, and then the link to the image on the line below it. (See bug
screenshot 4)
2) If the user manually moves each image link up to the previous line after the
text (the numbered step it wishes to be apart of in the numbered list) and
saves the page, it will appear correctly with the numbered list not being reset
to 1 for every list item. (See bug screenshot 5 and bug screenshot 6)

I'm not sure of the details on how to go about fixing this, but I would say VE
needs to make sure that the image link wiki markup stays on the same line as
the list item.

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