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If I delete a file on a network share from a windows client with something like eraser, will it overwrite the actual blocks of data of said file over and over or will it write out all over the place as it is told to write zeros? How accurate would it be?

In this case the file share is windows, a guest OS inside a ESXi host, on magnetic disks on a 20 disk raid 6 array connected via iSCSI

lotsofjam
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This isn’t guaranteed. Server may run snapshots with his local file system, it even can be something like WAFL, CASL or LSFS where every next data or metadata write happens @ new logical block address. The only way to resolve this is to physically disconnect your hard disks from your server and run something like DBAN against them.

https://dban.org/

RiGiD5
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