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Questions about Supporting Large file uploads

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I have a project where I am required to support processing on somewhat large jpeg files. So far I have written a Filewatcher program in c# that works fine locally, but cannot seem to process the files on the webserver on upload. I am really not sure how to proceed on this, since the filewatcher needs to watch the uploads directory and all subdirectories, it also needs to run a program against these files once they are uploaded, and that is an exe file, I do have it working on a local directory but I can't seem to make the leap to get it working on the server. I have tried several approaches including adding a grunt task but I have not been able to get that to work either. Hoping someone can help me figure out how to do this or point me to a tutorial that covers this type of use case.

I have the site creating subdirectories under uploads with the users email address upon login, I am also able to upload files, but when I try to run my file monitor program it just errors out. I realize this question isn't written the best in the world trying to convey the problem without adding extraneous details


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