Using the Security & Compliance Center PowerShell and the advanced settings options, I have created two OutlookCollaborationRules to customize the pop-up messages for Outlook. The Rule1 is a BLOCK and uses LabelA, the Rule2 is a WARN and uses LabelB. Rule2 is not working, only Rule1. I have also configured the "outlookblockuntrustedcollaborationlabel" for LabelA and the "outlookwarnuntrustedcollaborationlabel" for LabelB. I have tested each rule individually to make sure there are no configuration issues with the json file and when used one at a time, they both work correctly. Am I missing something in the configuration to allow for more than one customized pop-up? Thanks.
Update - This is a bug with the current AIP Unified Client (2.11.58). If an image file is located in the Outlook email, only one customized pop-up will work (we have image files in our company signatures). Removing the image solved the problem. The next version of the AIP Unified Client is supposed to fix this.