TLS is the most widely used cryptographic protocol on the Internet. While many recent studies focused on its use in HTTPS, none so far analyzed TLS usage in e-mail related protocols, which often carry highly sensitive information. Since end-to-end encryption mechanisms like PGP are seldomly used, today confidentiality in the e-mail ecosystem is mainly based on the encryption of the transport layer. A well-positioned attacker may be able to intercept plaintext passively and at global scale. In this paper we are the first to present a scalable methodology to assess the state of security mechanisms in the e-mail ecosystem using commodity hardware and open-source software. We draw a comprehensive picture of the current state of every e-mail related TLS configuration for the entire IPv4 range. We collected and scanned a massive data-set of 20 million IP/port combinations of all related protocols (SMTP, POP3, IMAP) and legacy ports. Over a time span of approx. three months we conducted more than 10 billion TLS handshakes. Additionally, we show that securing server-to-server communication using e.g. SMTP is inherently more difficult than securing client-to-server communication. Lastly, we analyze the volatility of TLS certificates and trust anchors in the e-mail ecosystem and argue that while the overall trend points in the right direction, there are still many steps needed towards secure e-mail.