The STARTTLS implementation in the server in Ipswitch IMail 11.03 and earlier does not properly restrict I/O buffering, which allows man-in-the-middle attackers to insert commands into encrypted SMTP sessions by sending a cleartext command that is processed after TLS is in place, related to a "plaintext command injection" attack, a similar issue to CVE-2011-0411.

Multiple buffer overflows in Ipswitch IMail before 2006.21 allow remote attackers or authenticated users to execute arbitrary code via (1) the authentication feature in IMailsec.dll, which triggers heap corruption in the IMail Server, or (2) a long SUBSCRIBE IMAP command, which triggers a stack-based buffer overflow in the IMAP Daemon.

Multiple buffer overflows in the IMAILAPILib ActiveX control (IMailAPI.dll) in Ipswitch IMail Server before 2006.2 allow remote attackers to execute arbitrary code via the (1) WebConnect and (2) Connect members in the (a) IMailServer control; (3) Sync3 and (4) Init3 members in the (b) IMailLDAPService control; and the (5) SetReplyTo member in the (c) IMailUserCollection control.

IMail stores usernames and passwords in cleartext in a cookie, which allows remote attackers to obtain sensitive information.

Stack-based buffer overflow in the IMAP server for Ipswitch IMail 8.12 and 8.13, and other versions before IMail Server 8.2 Hotfix 2, allows remote authenticated users to cause a denial of service (crash) via a SELECT command with a large argument.

IMail POP3 daemon uses weak encryption, which allows local users to read files.