My wife was having a hard time attaching photos to emails with hotmail. I figured she was doing something wrong. (She is not computer savy by any means) So I tried it and it is amiss.
On my Windows XP machine if you go into your hotmail account, there is an attach button. When you cursor over it a drop down comes up, and shows File or Photo. If you click Photo, and browse to a folder with pictures it comes up with thumbnails, and tick boxes. Then you tick the ones you want, and send away. In Windows 7, the attach button is there but no drop down for File or Photo. You can select pictures, but not as easily. Also, XP seems to compress the photos, and you can send more under the 10MB attachment limit. In Win 7 you may get to send 2, as most of my pictures are around 4.5MB.
Both machines are running IE 8, and are current as far as updates. Anybody have a clue? Sooner the better before I'm sent to the dog house. LOL