Issue with self-signed Extensions

I am packaging my extension with self signed cert that is created with the ZXPSignCmd executable.
It functions correctly and the -verify command confirms the ZXP is good to go.
When a user install the extension, however, it only functions once the first time they open Illustrator after installing it. Every time after that, when Illustrator is opened, the panel is completely blank.
This issue can be resolved by enabling PlayerDebugMode on the end-user's .plist file (as outlined for developers in the blog) but obviously this is something I do not want the end user doing. Does anyone have insight as to why the extension panel only loads once, and then breaks? Enabling PlayerDebugMode addresses the issue, but I can't figure out why. I assume is has something to do with the the way it is signed, but I would like confirmation/clarification if anyone knows what is going on.

Ok, I've validated my html and I'm getting a few errors related to Angular. They're all one of two types of errors
Error 1:
<div ng-controller="ExampleController">
Gets the following error:
Attribute ng-controller not allowed on element div at this point.
Error 2:
<my-directive></my-directive>
Gets the following error:
Element my-directive not allowed as child of element div in this context. (Suppressing further errors from this subtree.)
Error 1 is for any Angular related thing...ng-click, ng-controller, ng-show, etc.
Error 2 appears where all my custom directives are.
I did a comparison between the not-working extension and a working one that also uses Angular (without any custom elements). When I validated the working extension, it returned a bunch of Error 1's but no Error 2's (this is expected, seeing as there are no custom elements).
To your question about dynamic HTML - there is none. All of the files are static after they're installed. I double checked this by running a diff-merge between the extension before and after it has been run once. They are exactly the same, so no files are changing.
There are known issues with custom directives in older browsers like IE8 - http://www.befundoo.com/blog/angularjs-directives-in-ie8/
Out of curiosity, I tried adding elements in the head, as described in the above blog, inside my extension. This did not have any effect, and the extension still fails.
I'm considering rewriting my directives as attributes instead of elements, and seeing if that does it. That would take some time though, so if the above info helps narrow down the problem or raises other questions of yours, I'm all ears! Thanks again for all the replies!

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