After upgrading to WordPress 2.7 awhile back, I noticed they included a flash uploader for images. However, I never did get it to work as I was unsure what to do with the following UI:
I ended up switching over to the browser uploader, which has worked for me.
The other day I decided to go figure out what was wrong. At first I thought it was because I didn’t have the latest version of Flash, but even after upgrading to Flash 10, it still did not work. Then I thought maybe it only works in IE and not Firefox, but even on IE with the latest version of Flash, it didn’t work.
I started researching the issue online and found: Flash Upload Not working in Latest 2.7 ver
Turns out the version of swfupload included with WordPress is incorrect or broken. I went to swfupload – Google Code and download the latest version, and overwrote the files in /wp-includes/js/swfupload. The only file you really need to keep in there is handlers.js.
Now the flash uploader is working like a charm: