Searching for a freeware that would replace file names with numbers, while simultaneously changing their current order with a random one, I found nothing!

All renaming utilities were able to just replace the names with numbers, but the wouldn’t add random numbering!

Fortunately, the solution to this problem can be achieved using special, but not difficult, settings in this nice freeware called Bulk Rename Utility. It is not obvious how you can enjoy random renaming, but it is easy.

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First load the folder that contains all those files you want renamed. Usually you do this by right clicking on a folder and selecting “Bulk Rename”. Then go to the “Action” menu and select “Random Sort“.

This will change the current order of your files, which normally follows their current names or modification dates, etc.

After you apply “Random Sort”, you can apply auto-numbering and full replacing of their original names, to have your files named in a sequence of numbers that will reflect their new, random, order.
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Please note: to be sure that no conflicts occur, if you already have some of your files named after numbers, select a many-digits numbering. E.g., if you have 500 files to rename, do not select a sequence from 1-500, or from 001 to 500, but from 0001 to 0500. In any case, Bulk Rename Utility will notify you about all errors, it will even undo any renaming already done, so that you will have the chance to understand and eliminate all possible conflicts.

* Check also this list with the best free file rename applications. Enjoy!