MailKit is a cross-platform mail client library built on top of MimeKit. A STARTTLS Response Injection vulnerability in versions prior to 4.16.0 allows a Man-in-the-Middle attacker to inject arbitrary protocol responses across the plaintext-to-TLS trust boundary, enabling SASL authentication mechanism downgrade (e.g., forcing PLAIN instead of SCRAM-SHA-256). The internal read buffer in `SmtpStream`, `ImapStream`, and `Pop3Stream` is not flushed when the underlying stream is replaced with `SslStream` during STARTTLS upgrade, causing pre-TLS attacker-injected data to be processed as trusted post-TLS responses. Version 4.16.0 patches the issue.

MimeKit is a C# library which may be used for the creation and parsing of messages using the Multipurpose Internet Mail Extension (MIME), as defined by numerous IETF specifications. Prior to version 4.15.1, a CRLF injection vulnerability in MimeKit allows an attacker to embed \r\n into the SMTP envelope address local-part (when the local-part is a quoted-string). This is non-compliant with RFC 5321 and can result in SMTP command injection (e.g., injecting additional RCPT TO / DATA / RSET commands) and/or mail header injection, depending on how the application uses MailKit/MimeKit to construct and send messages. The issue becomes exploitable when the attacker can influence a MailboxAddress (MAIL FROM / RCPT TO) value that is later serialized to an SMTP session. RFC 5321 explicitly defines the SMTP mailbox local-part grammar and does not permit CR (13) or LF (10) inside Quoted-string (qtextSMTP and quoted-pairSMTP ranges exclude control characters). SMTP commands are terminated by <CRLF>, making CRLF injection in command arguments particularly dangerous. This issue has been patched in version 4.15.1.