I do not have links handy but there are DLP solutions for enterprise tools like gmail, google docs, etc... They do not need to MiTM connections are the tool ha

I do not have links handy but there are DLP solutions for enterprise tools like gmail, google docs, etc... They do not need to MiTM connections are the tool has administrative access to the corporate account. Many companies use these tools to check the box in their audits around data integrity and data exfiltration. This only works for corporate accounts. Most corporate enterprise cloud services have an API for DLP monitoring. Personal accounts would require a going through a process for lawful intercept. I have no idea how formal this process is today or if Google even ask for a copy of the warrant. When I set up monitoring for cell phone conversations in the cellular industry, not at google I always had a copy of the warrant.