sendmail through 8.17.2 allows SMTP smuggling in certain configurations. Remote attackers can use a published exploitation technique to inject e-mail messages with a spoofed MAIL FROM address, allowing bypass of an SPF protection mechanism. This occurs because sendmail supports <LF>.<CR><LF> but some other popular e-mail servers do not. This is resolved in 8.18 and later versions with 'o' in srv_features.

ALPACA is an application layer protocol content confusion attack, exploiting TLS servers implementing different protocols but using compatible certificates, such as multi-domain or wildcard certificates. A MiTM attacker having access to victim's traffic at the TCP/IP layer can redirect traffic from one subdomain to another, resulting in a valid TLS session. This breaks the authentication of TLS and cross-protocol attacks may be possible where the behavior of one protocol service may compromise the other at the application layer.

The sm_close_on_exec function in conf.c in sendmail before 8.14.9 has arguments in the wrong order, and consequently skips setting expected FD_CLOEXEC flags, which allows local users to access unintended high-numbered file descriptors via a custom mail-delivery program.

sendmail before 8.14.4 does not properly handle a '\0' character in a Common Name (CN) field of an X.509 certificate, which (1) allows man-in-the-middle attackers to spoof arbitrary SSL-based SMTP servers via a crafted server certificate issued by a legitimate Certification Authority, and (2) allows remote attackers to bypass intended access restrictions via a crafted client certificate issued by a legitimate Certification Authority, a related issue to CVE-2009-2408.

Use-after-free vulnerability in Sendmail before 8.13.8 allows remote attackers to cause a denial of service (crash) via a long "header line", which causes a previously freed variable to be referenced. NOTE: the original developer has disputed the severity of this issue, saying "The only denial of service that is possible here is to fill up the disk with core dumps if the OS actually generates different core dumps (which is unlikely)... the bug is in the shutdown code (finis()) which leads directly to exit(3), i.e., the process would terminate anyway, no mail delivery or receiption is affected."

Sendmail before 8.13.7 allows remote attackers to cause a denial of service via deeply nested, malformed multipart MIME messages that exhaust the stack during the recursive mime8to7 function for performing 8-bit to 7-bit conversion, which prevents Sendmail from delivering queued messages and might lead to disk consumption by core dump files.