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If a file is too large it will exceed the heap size limits on salesforce.com. There are a couple options here to identify too large of files.
Inspect the size of the files before upload to see if they are too large.
On failure of an upload capture error and display to user.
In either case need to provide some way to upload an individual large file with the normal upload component. I am thinking a modal windows that hosts a different page in an iframe. This will allow the main component to be re-rendered without issue.
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