I've been working on the posting tool - and on some matching back end code - all afternoon (well, other than the hour or so spent sledding with my daughter). Up until now, there was no support for uploading images to the server. I've been addressing that this afternoon, and I've got it working in test. What you can do is specify a set of files to upload, and then you can upload them to the server. They'll default into a subdirectory of the blog directory (the place where the SSP files live). I'll be rolling the new servlet into production shortly, and testing it myself. Once I'm sure it works, I'll release the new version of the client tool.