Ugh. People can't seem to figure out "sudo -i", or if so, do it to evade logging on monitored systems that should be locked-down.

# Prevent the trivial `sudo su -`
# Cmd_Alias SU = /usr/bin/su, /bin/su
# %wheel ALL=(ALL) NOPASSWD: ALL, !SU

And also, unfortunately, because of sudo's path-based "security" < 1.9.10 without regex matching, there's no sensible way to enforce who can run what except by lengthy allow lists and denying everything else.

# Prevent trivial interactive shell spawning
# Problem/feature: this allows `sudo chroot / bash -li`
# Cmd_Alias SBIN = /usr/sbin/*, /sbin/*
# Cmd_Alias SHELLS = /bin/bash, /bin/bash-static, /bin/busybox, /bin/busybox-static, /bin/csh, /bin/csh-static, /bin/dash, /bin/dash-static, /bin/fish, /bin/fish-static, /bin/ksh, /bin/ksh-static, /bin/ksh93, /bin/ksh93-static, /bin/lksh, /bin/lksh-static, /bin/mksh, /bin/mksh-static, /bin/pdksh, /bin/pdksh-static, /bin/rbash, /bin/rbash-static, /bin/rbusybox, /bin/rbusybox-static, /bin/rcsh, /bin/rcsh-static, /bin/rdash, /bin/rdash-static, /bin/rfish, /bin/rfish-static, /bin/rksh, /bin/rksh-static, /bin/rksh93, /bin/rksh93-static, /bin/rlksh, /bin/rlksh-static, /bin/rmksh, /bin/rmksh-static, /bin/rpdksh, /bin/rpdksh-static, /bin/rtcsh, /bin/rtcsh-static, /bin/rzsh, /bin/rzsh-static, /bin/sh, /bin/sh-static, /bin/tcsh, /bin/tcsh-static, /bin/zsh, /bin/zsh-static, /usr/bin/bash, /usr/bin/bash-static, /usr/bin/busybox, /usr/bin/busybox-static, /usr/bin/csh, /usr/bin/csh-static, /usr/bin/dash, /usr/bin/dash-static, /usr/bin/fish, /usr/bin/fish-static, /usr/bin/ksh, /usr/bin/ksh-static, /usr/bin/ksh93, /usr/bin/ksh93-static, /usr/bin/lksh, /usr/bin/lksh-static, /usr/bin/mksh, /usr/bin/mksh-static, /usr/bin/pdksh, /usr/bin/pdksh-static, /usr/bin/rbash, /usr/bin/rbash-static, /usr/bin/rbusybox, /usr/bin/rbusybox-static, /usr/bin/rcsh, /usr/bin/rcsh-static, /usr/bin/rdash, /usr/bin/rdash-static, /usr/bin/rfish, /usr/bin/rfish-static, /usr/bin/rksh, /usr/bin/rksh-static, /usr/bin/rksh93, /usr/bin/rksh93-static, /usr/bin/rlksh, /usr/bin/rlksh-static, /usr/bin/rmksh, /usr/bin/rmksh-static, /usr/bin/rpdksh, /usr/bin/rpdksh-static, /usr/bin/rtcsh, /usr/bin/rtcsh-static, /usr/bin/rzsh, /usr/bin/rzsh-static, /usr/bin/sh, /usr/bin/sh-static, /usr/bin/tcsh, /usr/bin/tcsh-static, /usr/bin/zsh, /usr/bin/zsh-static, /usr/local/bin/bash, /usr/local/bin/bash-static, /usr/local/bin/busybox, /usr/local/bin/busybox-static, /usr/local/bin/csh, /usr/local/bin/csh-static, /usr/local/bin/dash, /usr/local/bin/dash-static, /usr/local/bin/fish, /usr/local/bin/fish-static, /usr/local/bin/ksh, /usr/local/bin/ksh-static, /usr/local/bin/ksh93, /usr/local/bin/ksh93-static, /usr/local/bin/lksh, /usr/local/bin/lksh-static, /usr/local/bin/mksh, /usr/local/bin/mksh-static, /usr/local/bin/pdksh, /usr/local/bin/pdksh-static, /usr/local/bin/rbash, /usr/local/bin/rbash-static, /usr/local/bin/rbusybox, /usr/local/bin/rbusybox-static, /usr/local/bin/rcsh, /usr/local/bin/rcsh-static, /usr/local/bin/rdash, /usr/local/bin/rdash-static, /usr/local/bin/rfish, /usr/local/bin/rfish-static, /usr/local/bin/rksh, /usr/local/bin/rksh-static, /usr/local/bin/rksh93, /usr/local/bin/rksh93-static, /usr/local/bin/rlksh, /usr/local/bin/rlksh-static, /usr/local/bin/rmksh, /usr/local/bin/rmksh-static, /usr/local/bin/rpdksh, /usr/local/bin/rpdksh-static, /usr/local/bin/rtcsh, /usr/local/bin/rtcsh-static, /usr/local/bin/rzsh, /usr/local/bin/rzsh-static, /usr/local/bin/sh, /usr/local/bin/sh-static, /usr/local/bin/tcsh, /usr/local/bin/tcsh-static, /usr/local/bin/zsh, /usr/local/bin/zsh-static
# Cmd_Alias SAFER_BIN = /usr/bin/*, /bin/*, !SHELLS, !/usr/bin/env, !/bin/env, !/usr/bin/su, !/bin/su, !/usr/bin/sudo, !/bin/sudo
# %wheel ALL=(ALL) NOPASSWD: !ALL, SBIN, SAFER_BIN

With sudo 1.9.12+, the INTERCEPT feature attempts to police exec() further. (Unfortunately, most distros use old versions of sudo so this isn't a turnkey option.)