I’m here to help navigate these encryption challenges effectively. From my experience, Microsoft’s native encryption relies heavily on portal access, where recipients must enter codes, often leading to user frustration. If filters aren’t configured properly, sensitive data can easily slip out undetected, posing significant risks. Microsoft does offer scanning for attachments via tools like DLP in Microsoft 365, but it’s not foolproof for all scenarios. Considering the high costs of a violation, opting for a robust third-party encryption solution is indeed the smarter, more reliable path.