Using thunderbird-52.8.0, also tried 52.7.0, the enigmail buttons can be customized into the mail window to use, but the setting does not persist: The next mail window comes up without them again. A thunderbird-builtin button like print can be configured in or out just fine and persists. # emerge --info thunderbird Portage 2.3.40 (python 3.6.5-final-0, default/linux/amd64/17.1/no-multilib, gcc-7.3.0, glibc-2.26-r7, 4.17.1 x86_64) ================================================================= System Settings ================================================================= System uname: Linux-4.17.1-x86_64-Intel-R-_Core-TM-_i5-5200U_CPU_@_2.20GHz-with-gentoo-2.4.1 KiB Mem: 8105588 total, 3049052 free KiB Swap: 0 total, 0 free Timestamp of repository gentoo: Sat, 30 Jun 2018 14:00:01 +0000 Head commit of repository gentoo: b6ce3b44476b40621ca28f9ad12960eca0804d6c sh bash 4.4_p12 ld GNU ld (Gentoo 2.30 p2) 2.30.0 app-shells/bash: 4.4_p12::gentoo dev-lang/perl: 5.24.3-r1::gentoo dev-lang/python: 2.7.14-r1::gentoo, 3.6.5::gentoo dev-util/cmake: 3.9.6::gentoo sys-apps/baselayout: 2.4.1-r2::gentoo sys-apps/openrc: 0.34.11::gentoo sys-apps/sandbox: 2.13::gentoo sys-devel/autoconf: 2.13::gentoo, 2.69-r4::gentoo sys-devel/automake: 1.15.1-r2::gentoo sys-devel/binutils: 2.30-r2::gentoo sys-devel/gcc: 7.3.0-r3::gentoo sys-devel/gcc-config: 1.8-r1::gentoo sys-devel/libtool: 2.4.6-r3::gentoo sys-devel/make: 4.2.1::gentoo sys-kernel/linux-headers: 4.13::gentoo (virtual/os-headers) sys-libs/glibc: 2.26-r7::gentoo Repositories: gentoo location: /usr/portage sync-type: rsync sync-uri: rsync://rsync.gentoo.org/gentoo-portage priority: -1000 sync-rsync-verify-jobs: 1 sync-rsync-verify-metamanifest: yes sync-rsync-verify-max-age: 24 sync-rsync-extra-opts: ACCEPT_KEYWORDS="amd64" ACCEPT_LICENSE="Apache-2.0 BSD BSD-2 BSD-4 GPL-1+ GPL-2 GPL-2+ GPL-3 GPL-3+ HPND ISC LGPL-2 LGPL-2+ LGPL-2.1 LGPL-2.1+ MIT OFL-1.1 openssl public-domain vim ZLIB" CBUILD="x86_64-pc-linux-gnu" CFLAGS="-O2 -pipe -march=native" CHOST="x86_64-pc-linux-gnu" CONFIG_PROTECT="/etc /usr/share/gnupg/qualified.txt" CONFIG_PROTECT_MASK="/etc/ca-certificates.conf /etc/env.d /etc/fonts/fonts.conf /etc/gconf /etc/gentoo-release /etc/init.d /etc/revdep-rebuild /etc/sandbox.d /etc/terminfo /usr/share/X11/xkb" CXXFLAGS="-O2 -pipe -march=native" DISTDIR="/usr/portage/distfiles" EMERGE_DEFAULT_OPTS="--quiet-build --misspell-suggestions n --rebuild-if-new-rev n " ENV_UNSET="DBUS_SESSION_BUS_ADDRESS DISPLAY PERL5LIB PERL5OPT PERLPREFIX PERL_CORE PERL_MB_OPT PERL_MM_OPT XAUTHORITY XDG_CACHE_HOME XDG_CONFIG_HOME XDG_DATA_HOME XDG_RUNTIME_DIR" FCFLAGS="-O2 -pipe" FEATURES="assume-digests binpkg-logs config-protect-if-modified distlocks ebuild-locks fixlafiles ipc-sandbox merge-sync multilib-strict network-sandbox news nodoc noinfo parallel-fetch preserve-libs protect-owned sandbox sfperms strict unknown-features-warn unmerge-logs unmerge-orphans userfetch userpriv usersandbox usersync" FFLAGS="-O2 -pipe" GENTOO_MIRRORS="http://distfiles.gentoo.org" LANG="C" LDFLAGS="-Wl,-O1 -Wl,--as-needed" PKGDIR="/usr/portage/packages" PORTAGE_COMPRESS="xz" PORTAGE_CONFIGROOT="/" PORTAGE_RSYNC_OPTS="--recursive --links --safe-links --perms --times --omit-dir-times --compress --force --whole-file --delete --stats --human-readable --timeout=180 --exclude=/distfiles --exclude=/local --exclude=/packages --exclude=/.git" PORTAGE_TMPDIR="/tmp" USE="X amd64 berkdb bzip2 cli crypt cxx dri fortran hardened iconv jpeg libtirpc minimal modules ncurses nptl openmp pcre png readline seccomp ssl tcpd unicode zlib" ABI_X86="64" CPU_FLAGS_X86="mmx mmxext sse sse2" ELIBC="glibc" INPUT_DEVICES="libinput keyboard mouse" KERNEL="linux" OFFICE_IMPLEMENTATION="libreoffice" POSTGRES_TARGETS="postgres9_5 postgres10" PYTHON_SINGLE_TARGET="python3_6" PYTHON_TARGETS="python3_6" USERLAND="GNU" VIDEO_CARDS="amdgpu fbdev intel nouveau radeon radeonsi vesa dummy v4l" Unset: CC, CPPFLAGS, CTARGET, CXX, INSTALL_MASK, LC_ALL, LINGUAS, MAKEOPTS, PORTAGE_BINHOST, PORTAGE_BUNZIP2_COMMAND, PORTAGE_COMPRESS_FLAGS, PORTAGE_RSYNC_EXTRA_OPTS ================================================================= Package Settings ================================================================= mail-client/thunderbird-52.7.0::gentoo was built with the following: USE="crypt hardened jemalloc minimal system-harfbuzz system-icu system-jpeg system-libevent system-libvpx system-sqlite -bindist -custom-cflags -custom-optimization -dbus -debug -gtk2 -ldap -lightning -mozdom (-neon) -pulseaudio (-rust) (-selinux) -startup-notification (-system-cairo) -wifi" L10N="-ar -ast -be -bg -bn-BD -br -ca -cs -cy -da -de -el -en-GB -es-AR -es-ES -et -eu -fi -fr -fy -ga -gd -gl -he -hr -hsb -hu -hy -id -is -it -ja -ko -lt -nb -nl -nn -pa -pl -pt-BR -pt-PT -rm -ro -ru -si -sk -sl -sq -sr -sv -ta-LK -tr -uk -vi -zh-CN -zh-TW"
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Which version of enigmail ? This seems like it's an enigmail issue rather than a thunderbird one, if native thunderbird buttons work as expected...
I had tried 2.0.5-r1 and 2.0.7. Sorry for not including this in the report, I was _very_ shure it's Thunderbird's job to deal with it's buttons, no matter who provides them. Less thinking, more reporting :) I just tried enigmail-1.9.9 (after editing the thunderbird-52.8.0 ebuild's minimum version requirement). Indeed that version's buttons can be customized in and out just fine, so I was allwrong and you are right and this looks like an enigmail issue.
Closing as obsolete, version is no longer available within Gentoo repository. Feel free to file a new bug against current supported version is problem is still present.