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10 .msi files with 1000MB each
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All of them would fit just fine
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3 .tar.gz files with 5GB each
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A .zip file with 1024MB
EXPLANATION
Since your flash drive is formatted with the FAT32 file
system, any file that is larger than 4GB will not be placed there. This
type of a file system has a built-in limitation on the size of the files
that it may contain. Although the total size of the files that you can
copy to a FAT32 drive could be as large as 2TB (or the physical capacity
of the drive, whichever is smaller), the size of each individual file
may not exceed 4GB.
This limitation may sound silly: why would anyone design a system
that would not allow for the larger files? The problem is, when the
FAT32 file system was designed (that was back in the days of Windows
95), no one anticipated that we would have such large files in use
today. Or, maybe the designers hoped that by the time such large files
became common, the use of the FAT32 system would be replaced by more
modern systems.