I have been using wordpress.com for a few years and I've never had this issue. For some reason, the photo uploader has not been working effectively over the past week or so. I've tried updating my browser (Safari), switching browsers (to Google Chrome), and switching from the "drag-and-drop uploader" to the "browse uploader" all with no success. Once in awhile, I can close my internet browser, re-open it, and successfully downloaded one photo, but the second one won't work (either in a post or just to the library).
Usually, the post appears to have downloaded (100%, sometimes even "Crunching" after that), but the additional dialog box that allows you to rename and save the photo never appears. The "Show" hyperlink also never appears.
Like I said, I've been able to get it to work about 10% of the time, but not consistently at all. Any help would be greatly appreciated!
The blog I need help with is crashleadership.com.