It seems that there is a error with the current build of windows live writer when posting images to the blog. Every time i posted it would seems that it would just overwrite the image instead of making a new folder. The crew at windows live team gave me a fix I thought i would share it. They say it will be fixed “soon”.
Open regedit
2. Open HKCU\Software\Microsoft\Windows Live\Writer\Weblogs\{blog-id}\UserOptionOverrides\, where {blog-id} is a GUID. You will have several of these, but should be able to tell the right one by looking at the contents of the key.
3. Add a new String value with name “fileUploadNameFormat” (case matters!!) and the value
{WindowsLiveWriter}/{PostTitle}/{Randomizer}/{AsciiFileName}