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The ever-evolving email encryption landscape only underscores email’s risks. Email service providers and encryption software makers need to continually up their game because they know organizations use email to transmit their most sensitive content—a fact that also attracts the sharpest cybercriminals. Yes, encrypted email is a challenging target, but it’s fortified precisely because it often carries the most valuable data. In this paper, we’ll explore several technical and behavioral reasons that email—even encrypted email—is not sufficiently secure for transmitting your sensitive and government regulated data.