I don't think I've encrypted an actual email even once. However, I do encrypt attachments or drop-box blobs from time to time. E.g., I might make a self-extrac

I don't think I've encrypted an actual email even once. However, I do encrypt attachments or drop-box blobs from time to time. E.g., I might make a self-extracting PGP archive of a directory of tax info encrypted with a symmetric key, put it on Google Drive, and send the link to my accountant, having shared the key out of band.