Did you reboot your I -pad and or your receiver too? I do this just about every time and it fixes it. So do signing in and out of my DISH anywhere account on my I pad. OF course you need to have internet connection that is strong and working too.
This simply means kill the app (double click the home button and swipe away Dish Anywhere), relaunch the app. Try transferring the show again. It typically works for me the very next time that I launch the app. It's been happening for me for the past several versions of the Dish Anywhere app.
The bug that really annoys me is not being able to resume playing a show that has already been transferred. The show just restarts at the beginning. Currently running Dish Anywhere V6.20.26 iOS 9.1. Hopper with Sling Software Version S525