Does client side S/MIME (which is E2E) work in Gmail/Google Apps provided you have a client that supports it (e.g. Outlook)? If so, I'm not sure what the probl

Does client side S/MIME (which is E2E) work in Gmail/Google Apps provided you have a client that supports it (e.g. Outlook)? If so, I'm not sure what the problem is with them not officially supporting it other than the awkwardness of dealing with certificates.