Media Permalinks

I’m having trouble understanding how the application applies a permalink name to my media when I upload it. Some of my media have names within the permalink that have no relation to the photo or where the photo came from or where it is assigned. I am mystified as to how this works and really would appreciate an understanding of how this process works. The documentation I have read doesn’t seem to address my issue. My website is working and this does not seem to be a problem with how it functions but it does bother my idea of continuity in naming conventions. I am using the post name under the common settings and my website is http://www.mostabear.com.

HELP! and Thanks a bunch to whoever can clear this muddy issue up for me.