Hi Kevin,
Below are answers to your questions.
1. Do you have policies that are monitoring for those actions? : Yes, my policies says to monitor all the protocols.
2. What browser are you using to upload?: I am using Mozilla Firefox, ver 58.
4. Has your monitoring filters been modified in the Agent Configuration?: Yes
5. Are both document types hitting the same printer? What version of office is it?: Yes, its hitting the same printer. office ver is 2016.
Cuurently the DLP version what we have is 14.5
Thanks