standard disclaimer: You use this at your own risk - you should review the code and ensure you understand what it is doing before running. I am in no way responsible for any damages etc etc that may be caused.
Powershell based DLP testing tool - presently for email attachments, but you can use the results of the scripts as source material to put into sites like https://dlptest.com/ - postman (https://www.postman.com) is a good tool to use to automate the http posting proceedure.
run ./delphos.ps1 once you have edited it and the other scripts (you need to enter in mail server configurations etc) to execute the various tests you wish. Requires MS Office (presently).
Super 'hacky' and a lot of code from various places - apologies if i cannot attribute where (so long ago now but if you recognise your stuff, drop me a line and ill add your name in), but it works, so please be gentle! ;)
Some scripts may require some raw data in a csv format if it doesn't generate it - should be easy to find online (Fake PCI/Credit card generator)