Took me a VERY long time to figure this out, but...
Problem: Files over 4GB cannot be dragged onto your external HDD if the external HDD is using FAT32 file-system.
Solution: Split the file up using terminal into chunks smaller than 4GB and transfer as usual. You can use terminal to join the file up again at a later time.
To split the file up into 1GB chunks:
split -b 1024m filename.file PREFIX_
To join the file from the separated chunks:
cat sub1 sub2 sub3 sub4 > output.file
I read somewhere the older macs cannot handle splits larger than 2047mb. This is not true on my mac because I just made chunks that are 3gb FTW.
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