out-of-chronological-order mess... Just Windows default behavior - does date sorting on a character-by-character basis,and the default North American convention of mm-dd-yy means that the year gets parsed last. Suppressed/implicit leading zeroes also cause some weird behavior in the sorts, in my experience,too.
see <http://forums.cnet.com/5208-6142_102-0.html?threadID=292241> for a discussion of this problem, and M$ other sorting inconsistencies at <http://support.microsoft.com/default.aspx?scid=kb;en-us;318872>. The photo cataloging software I currently use has the option to use the date embedded in the EXIF data,or add info to the ITPC metadata.