For this example, a picture must be inserted in the Edit via Office session, in the normal MS Word way. That is, select the top level menu Insert, and then Picture then from File, then browse and select your file.
After in inserting, the picture is displayed in the MS Word session (that was opened using Edit via Office):
Figure: View of Inserted Picture
Now, after a few edits, the MS Word session is saved and closed (don't do a Save As...). When the wiki has finished uploading, the properties will be updated with a new attachment.
Figure: Properties of Uploaded Work Item with Picture Added in Edit via Office