When vt fails to upload a file, no error is issued
There are times when images upload fail like in this case: #768 (closed)
Vtiger doesn't warn the user. It just doesn't upload the file without letting you know.
If you go to the listview of documents you can see --
in the cases were the images could not be uploaded:
However I think that is not enough. Because if the file is uploaded from the documents widget in the summary view of another module or from the customer portal, the user just goes on assuming the file was uploaded.