I just noticed this on 14.20 with my FR255, but don't know if it existed already.
I had 3 apps installed via Connect IQ. They were at the end of my apps list on the phone. I wanted to delete the third item from the end.
I went into the long-press UP button, scrolled to Settings / Activities & Apps, selected it with the START button, scrolled to the app and selected it with START, then scrolled to Delete from Device and selected that with the START button. All of this made sense to me up to this point.
But, when it returned to the app list, it was still showing the app name I thought I just deleted. I stupidly assumed I might have clicked a cancel option instead of delete, so while still showing the same app name I clicked START again and scrolled to Delete from Device and clicked START again, which sent me back to the same broken place again. Then I realized something else is going on here.
Long story short, the Delete from Device action doesn't synchronize its changes to the app list where you return immediately after the operation. So, the second time I clicked START, it actually opened the menu to manage a different app than the one highlighted with the vertical bar. The indicated name was for an app that did not exist on the device anymore, while I was actually selecting the subsequent app in the list.
As a result, I deleted the subsequent app by accident on the second attempt.