Windows Live Writer not working with WordPress? The problem is caching
I use Windows Live Writer to create posts on WordPress sites all the time. It’s a very good tool and, with plugins, has a huge range of functions. One of its cooler features is that it can create a test post on your blog and use it to download the theme, so it appears as if you are writing in a live post. I recently tried to set it up with two new blogs I’d just set up and I could not get it to pick up the theme. I was puzzled for quite a while.
I played around with the blog, trying to figure out what had gone wrong. Then, all of a sudden it dawned on me. I use WP-Super-Cache to keep my WordPress sites stable and Windows Live Writer was seeing the cached version of the site and was unable to see the new post it had put up.
So the solution is to turn off your caching plugin when you configure WLW. Just do that and it works fine.