My brother has a laptop with windows XP. He right clicks on a picture and chooses: send to -> mail recipient. He then tries to shrink the picture. Windows Explorer encounters an error and shuts down.
Sounds like your bro is trying to do too much too soon. WinEx expects to either 'send mail' OR 'shrink picture'. Not both at once. It will do better if he right clicks, saves pix to his harddisk, then shrink with whatever program he wants, and then mails (as an attachment).
it should work as widows doesn't try to do both at once ,it will resize it then open you e-mail program and add the attachment . may have to do with just how big the picture is and maybe its file type .