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File Manager and File Upload crash with large files. Small ( I tested with a 5 MEG) file works OK. A large, 600 MEG file crashed the process. Webmin 1.630 on Ubuntu 12.04 server.
The issue here is that files being uploaded have to be read into memory, possibly duplicated multiple times. Webmin doesn't currently support any kind of "streaming" upload that writes directly to the destination file.
For big uploads like that, I'd recommend using FTP or SSH.