Why is my file too large for the destination file system?

The issue being larger than the destination file system does not always mean that the destination hard drive has not enough free space. In fact, this is a file system-related issue and not an availability of sufficient storage. To give an example, the maximum size of a single file on a FAT32 file system is about 4 gigabytes. It would be a good idea to check what kind of file system the destination hard drive uses in Windows. If you need to transfer large files regularly, then it would be better to use NTFS or exFAT drives.

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