Perhaps you can rephrase and clarify the question.
Robert
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I'm not sure what you mean by data expiration date. You'll have to
write something to delete entities.
I'm also not sure what you mean by files. Are you talking about
application files, blobs, datastore entities, something else?
Robert
If you write the cron, then you can use the blobstore delete function:
http://code.google.com/appengine/docs/python/blobstore/functions.html#delete
Or, if you're actually storing a BlobProperty in the datastore:
http://code.google.com/appengine/docs/python/datastore/functions.html#delete
Robert