Overview of Data Loss Prevention (DLP) in Office 365 

Thank you so much for your wonderful feedback..

You welcome.

As per the testing I have done.it also validates the password protected files..

DLP policy created in Office 365 can find and protect sensitive information located in Exchange Online, SharePoint Online and OneDrive for Business. And the conversation History of Skype for Business stored in Exchange server which is in turn protected. But if you want the IM between Skype for Business clients to be protected by DLP, It’ not feasible to monitor the information in Skype for Business. For detailed information, please refer to this article:support.office.com/en-us/article/Overview-of-data-loss-prevention-policies-1966b2a7-d1e2-4d92-ab61-42efbb137f5e .

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currently you have an option creating policy and test with one user oo you have an option to evaluate