Does anyone else have this problem? Instead of overwriting my save occasionally it will create a new one even though it asks "Are you sure you want to overwite this save?".
For me, it had to do with the savegames being 'read only' in the save game folder "documents/My Games/Skyrim" when I ticked that off, overwriting did what it's supposed to.
This bug is caused by SKSE, i suppose you use SkyUI. Launch Skyrim without SKSE and you'll see that the saves will be overwritten.
I reported that nasty bug three weeks ago on the SKSE dedicated topic (http://www.gamesas.com/topic/1400450-wipz-skyrim-script-extender/page__view__findpost__p__21330874) but it seems that nobody cares...