I found the solution to this issue...
I am amazed at the lack of documentation of not pointing this, so not obvious, problem...
When the Json is Serialized and written in the HTTPContext.Response, the Json file by default when you download the Plug in is by default Structured this way
[
{
name: "pic.jpg",
type: "IMAGE",
size: "123123".
},
{
name: "pic2.jpg",
type: "IMAGE",
size: "123432443".
}
]
Since their documentation says that the files are ready to be used when downloaded, I wouldn't think that this would be the reason why the Files are uploaded but not displayed correctly in the Table.
However in their Documentation is a small example of how the JSON file should look like but its easily overlooked if not payed close attention.
[
{ "files":
{
name: "pic.jpg",
type: "IMAGE",
size: "123123".
},
{
name: "pic2.jpg",
type: "IMAGE",
size: "123432443".
}
} ]
Once Changed to this format. the Uploader correctly uploaded the files and no longer had an issue in showing them after.