Sending documents off to coworkers and customers won't tax your technological resources, but most email servers pitch a fit if you try to mail anything larger than 25MB in size. YouSendIt's whole business revolves around transferring files that are much bigger than an average attachment. The service lets you upload individual files of up to 2GB to a cloud storage locker of unlimited size, and then share a link to that file with other people. It's all protected by 128-bit SSL encryption along with file-specific passwords, download tracking, and authenticated delivery options—if you're a $14.99 monthly member. Free subscribers are limited to 2GB of storage and get capped at 50MB file transfers. Alternatively, Box subscribers can share 2GB files with others.