Identity Problem.
elementInsertedByDropping !== elementSelectedAndDragged
In the console, one can verify the assertion above. So that narrows down the category of problem to a relatively familiar one.
I'm learning Angular myself, and I'm also having trouble with ui-sortable; please don't regard my opinions as definitive. However, I believe that the problem is that the $watch listeners need to be re-bound to the new element, as it is being created asynchronously outside of Angular.
The "ng.$rootScope.Scope" documentation describes this situation somewhat clearly in the $apply section. If I am correct, you would need to either $scope.$apply(...) code in your controller, or [preferably] write a custom directive that handles the insertion.
Fortunately, it seems that jQuery-ui-sortable's "update" event can be easily used in a custom directive to ensure that the element is bound. I found that bloggers respectTheCode and Michal Ostruszka discuss the problem of writing jQuery-ui-sortable directives in fairly clear terms; so does a fellow named Greg Gigon and several others, but I'm only allowed to offer you two links at this point.
If I can provide more precise information at a later point, I will revise this answer; I'm still learning this stuff myself, and I would like to know how to do something quite similar.
[edit: I'm not familiar enough with Angular-UI-Sortable to know whether this is a bug or simply missing functionality.]
raw.github.comlinks in your plunk:Refused to execute script from 'https://raw.github.com/angular-ui/ui-sortable/angular1.2/src/sortable.js' because its MIME type ('text/plain') is not executable, and strict MIME type checking is enabled.