Install app-crypt/gnupg-2.2.4-r2, which pulls in app-crypt/pinentry-1.0.0-r2. With a fresh ~/.gnupg, start a new gpg-agent with --daemon. Try to create a new key with gpg --gen-key (name and email are irrelevant). Use a simple passphrase, "accept" at the weak passphrase warning, and then deliberately typo the passphrase. pinentry-curses bails and GPG aborts with EOF. I noticed this when I was sending an encrypted message and I typo'd my passphrase. The above example is a clean way to demonstrate the issue. When I launch gpg-agent with "debug 1024" and "debug-pinentry" I get this out of the log: gpg-agent[7165]: DBG: chan_11 -> SETPROMPT Passphrase: gpg-agent[7165]: DBG: chan_11 <- OK gpg-agent[7165]: DBG: chan_11 -> [[Confidential data not shown]] gpg-agent[7165]: DBG: chan_11 <- [[Confidential data not shown]] gpg-agent[7165]: DBG: chan_11 <- [[Confidential data not shown]] gpg-agent[7165]: DBG: chan_11 -> SETERROR Bad Passphrase (try 2 of 3) gpg-agent[7165]: DBG: chan_11 <- OK gpg-agent[7165]: DBG: chan_11 -> [[Confidential data not shown]] gpg-agent[7165]: DBG: chan_11 <- [eof] gpg-agent[7165]: DBG: error calling pinentry: End of file <GPG Agent> Happy to help troubleshoot further, but I'm a bit out of my depth. strace wasn't particularly revealing. I think the problem lies with pinentry, but I'm not sure where specifically. Any help is very much appreciated! Thanks! $ emerge --info Portage 2.3.19 (python 3.5.4-final-0, default/linux/amd64/17.0, gcc-6.4.0, glibc-2.25-r10, 4.9.76-gentoo-r1 x86_64) ================================================================= System uname: Linux-4.9.76-gentoo-r1-x86_64-Westmere_E56xx-L56xx-X56xx_-Nehalem-C-with-gentoo-2.4.1 KiB Mem: 4055160 total, 67316 free KiB Swap: 8388604 total, 8388600 free Timestamp of repository gentoo: Sat, 24 Feb 2018 12:30:01 +0000 Head commit of repository gentoo: 0e378ee4ac6c6d935690b269842be810f3bb2211 sh bash 4.4_p12 ld GNU ld (Gentoo 2.29.1 p3) 2.29.1 app-shells/bash: 4.4_p12::gentoo dev-lang/perl: 5.24.3::gentoo dev-lang/python: 2.7.14-r1::gentoo, 3.5.4-r1::gentoo dev-util/cmake: 3.9.6::gentoo dev-util/pkgconfig: 0.29.2::gentoo sys-apps/baselayout: 2.4.1-r2::gentoo sys-apps/openrc: 0.34.11::gentoo sys-apps/sandbox: 2.12::gentoo sys-devel/autoconf: 2.69-r4::gentoo sys-devel/automake: 1.15.1-r1::gentoo sys-devel/binutils: 2.29.1-r1::gentoo sys-devel/gcc: 6.4.0-r1::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: 2.25-r10::gentoo Repositories: gentoo location: /usr/portage sync-type: rsync sync-uri: rsync://rsync.gentoo.org/gentoo-portage priority: -1000 sync-rsync-extra-opts: ACCEPT_KEYWORDS="amd64" ACCEPT_LICENSE="* -@EULA" CBUILD="x86_64-pc-linux-gnu" CFLAGS="-O2 -pipe" 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/gconf /etc/gentoo-release /etc/sandbox.d /etc/terminfo" CXXFLAGS="-O2 -pipe" DISTDIR="/usr/portage/distfiles" FCFLAGS="-O2 -pipe" FEATURES="assume-digests binpkg-logs config-protect-if-modified distlocks ebuild-locks fixlafiles merge-sync multilib-strict news parallel-fetch preserve-libs protect-owned sandbox sfperms strict unknown-features-warn unmerge-logs unmerge-orphans userfetch userpriv usersandbox usersync xattr" FFLAGS="-O2 -pipe" GENTOO_MIRRORS="http://www.gtlib.gatech.edu/pub/gentoo rsync://rsync.gtlib.gatech.edu/gentoo ftp://ftp.gtlib.gatech.edu/pub/gentoo http://lug.mtu.edu/gentoo/" LANG="en_US.UTF-8" LDFLAGS="-Wl,-O1 -Wl,--as-needed" MAKEOPTS="-j4" PKGDIR="/usr/portage/packages" 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="/var/tmp" USE="acl amd64 bash-completion berkdb bzip2 cli crypt cxx dri fortran gdbm iconv ipv6 modules multilib ncurses nls nptl openmp pam pcre readline seccomp ssl tcpd unicode xattr zlib zsh-completion" ABI_X86="64" ALSA_CARDS="ali5451 als4000 atiixp atiixp-modem bt87x ca0106 cmipci emu10k1x ens1370 ens1371 es1938 es1968 fm801 hda-intel intel8x0 intel8x0m maestro3 trident usb-audio via82xx via82xx-modem ymfpci" APACHE2_MODULES="authn_core authz_core socache_shmcb unixd actions alias auth_basic authn_alias authn_anon authn_dbm authn_default authn_file authz_dbm authz_default authz_groupfile authz_host authz_owner authz_user autoindex cache cgi cgid dav dav_fs dav_lock deflate dir disk_cache env expires ext_filter file_cache filter headers include info log_config logio mem_cache mime mime_magic negotiation rewrite setenvif speling status unique_id userdir usertrack vhost_alias" CALLIGRA_FEATURES="kexi words flow plan sheets stage tables krita karbon braindump author" COLLECTD_PLUGINS="df interface irq load memory rrdtool swap syslog" CPU_FLAGS_X86="mmx mmxext sse sse2" ELIBC="glibc" GPSD_PROTOCOLS="ashtech aivdm earthmate evermore fv18 garmin garmintxt gpsclock isync itrax mtk3301 nmea ntrip navcom oceanserver oldstyle oncore rtcm104v2 rtcm104v3 sirf skytraq superstar2 timing tsip tripmate tnt ublox ubx" INPUT_DEVICES="libinput keyboard mouse" KERNEL="linux" LCD_DEVICES="bayrad cfontz cfontz633 glk hd44780 lb216 lcdm001 mtxorb ncurses text" LIBREOFFICE_EXTENSIONS="presenter-console presenter-minimizer" OFFICE_IMPLEMENTATION="libreoffice" PHP_TARGETS="php5-6 php7-0" POSTGRES_TARGETS="postgres9_5" PYTHON_SINGLE_TARGET="python3_5" PYTHON_TARGETS="python2_7 python3_5" RUBY_TARGETS="ruby22 ruby23" USERLAND="GNU" VIDEO_CARDS="amdgpu fbdev intel nouveau radeon radeonsi vesa dummy v4l" XTABLES_ADDONS="quota2 psd pknock lscan length2 ipv4options ipset ipp2p iface geoip fuzzy condition tee tarpit sysrq steal rawnat logmark ipmark dhcpmac delude chaos account" Unset: CC, CPPFLAGS, CTARGET, CXX, EMERGE_DEFAULT_OPTS, INSTALL_MASK, LC_ALL, LINGUAS, PORTAGE_BUNZIP2_COMMAND, PORTAGE_COMPRESS, PORTAGE_COMPRESS_FLAGS, PORTAGE_RSYNC_EXTRA_OPTS
> > Happy to help troubleshoot further, but I'm a bit out of my depth. strace > wasn't particularly revealing. I think the problem lies with pinentry, but > I'm not sure where specifically. If pinentry SIGSEGVs , can you try to produce a backtrace using a core dump and gdb? (see ulimit -c unlimited and man gdb, mainly you start it up and do a "bt") To try pinentry directly, use e.g /usr/bin/pinentry <<<GETPIN That should hopefully help debugging without going through agent .. And to have it said, use a test password and not real one...
Need more info to debug, please reopen if adding the requested information