When I click upload, it doesn't look like it does anything but I click on close window and use the back arrow to go back to the text box, type my message, click submit and it appears on quiltingboard after that. I can also add a picture to an existing thread by using the icons above the regular reply section. As I am doing this post, I could go to the third little icon from the right above the text box and click on the tiny tree and it gives you a similar prompt box as the attachment icon. If you don't have a lot of little icons above your text box on your reply box, you need to go to settings and make an adjustment. Settings is up by your Welcome sentence at the top of the quiltingboard page.