Martin,
You’re not doing anything wrong. When Live Writer uploads the images, it automatically creates a down-sized thumbnail image (your first screenshot) and stores it on the site.
What you’re experiencing in the second screenshot is actually a feature of Live Writer, not a bug. WordPress has certain default image sizes for thumbnails, medium-size, and large-size (Go to Settings >> Media to see what they’re set to). Live Writer has its own default settings. In addition, you can re-size images in Live Writer, and it will upload both the re-sized and original size to the server.
At times, you’ll end up with several versions of the same image, both the Live Writer and WordPress default sizes and whatever size you told Live Writer to make the image.
So no, you’re not doing anything wrong and no, it’s not a bug.
Does anyone know if WordPress is planning on installing a feature like this to wordpress media manager? One that will automatically resize the image for you? I’m hosting my cousin’s blog and if she uses the built in image uploader she uploads about a gig of images b/c she has no idea how to crop and resize. Luckily I told her about live writer, but I’d prefer that it was built in. Anyone have any info?
WordPress 2.9 (and 2.9.1) allow you to edit and crop your images after you upload them. WordPress also automatically re-sizes large images to create smaller sizes and thumbnails when you upload. To see what your settings are, log in and go to Settings >> Media.
