Using Windows LiveWriter, I just went to publish my first blog post with pictures, since I moved onto my own dedicated server. I got an error that the blog does not support picture publishing, and it prompted me to configure FTP publishing for pictures instead. Oh no, why doesn’t this work!?
It took me about an hour of digging to find this answer, so here it is:
The account that WordPress runs as, needs to have read/write permission on the upload directory in WordPress.
For example: D:websitesblog.robseder.comwp-contentuploads
Grant that account read/write to that directory and you should be good. For me, once I did that, I could publish like normal and WordPress correctly stored the new image files out in the right year/month folder structure.