Let's say because of a conditional comment or just being careless the same included file is present for users of some browser or even all browsers. For example:
<!--[if lte IE 8]>
<script src="mygreatincludefile.js" type="text/javascript"></script>
<![endif]-->
<!--[if lte IE 6]>
<script src="mygreatincludefile.js" type="text/javascript"></script>
<![endif]-->
When the page is being rendered will the browser know not to bother to grab that file again or will it make a request and the browser will return 304 (not modified). The best case seems to be the first, the acceptable case seems to be the second option while the worst case would be that a fresh request would like be made because the browser doesn't know it just grabbed this yet.
Do you have experience with this sort of thing firsthand? What would you expect to happen? What have you observed happened? Should I just be not worrying about this and punch the person who did it keeping in mind that it may have been me?