ZIP multiple files at once, while each has its own password.


I need to ZIP, password protect and send approximately 300 files. Every file has to have its own unique password and has to be in single archive. I have been doing it one by one which is tedious :).

Do you know of any free or paid application that can do this at once, as a bulk operation?


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  1. No way to do this if you are using different passwords for each file.

    The only way I can think of is to run a script to pass characters to the system as keystrokes. Basically you will be scripting the clicks, and have a separate file with the different passwords that the scripts pulls down. The issue here is you need to know exactly what password got applied to what file, which will be pretty much alphabetical. And need to execute the clicks, and time to make sure that there is a file is open at the time you pass the password keystrokes to the window.
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