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Getting OutOfMemoryExceptions when uploading large files is a very common problem and we troubleshoot it quite frequently at Microsoft GTSC.
JohanS has a very nice entry on his blog and I can't resist myself to link to the solution which he provided!
<snip>
Problem:
Using the WebClient.Upload method for posting large files will eventually leave you stranded with OutOfMemoryExceptions.
Cause:
WebClient.Upload reads the entire file to memory by default.
Resolution:
Build your own uploader. Please click this link to read more!
</snip>
Thanks Johan, and please keep these coming!
Cheers,
Rahul