This is a regression that came with the TOCTOU race fix in kern_sig.c 1.216: https://cvsweb.openbsd.org/cgi-bin/cvsweb/src/sys/kern/kern_sig.c#rev1.216
Reverting that file to 1.215 and /sys/sys/signalvar.h to 1.28 makes this phenomenon go away. Consider the following session on amd64 current: $ cat > prog.c int main(void) { return 0; } $ cc -g prog.c $ gdb -q a.out (gdb) start Breakpoint 1 at 0x52d: file prog.c, line 4. Starting program: /tmp/a.out Breakpoint 1 at 0x6e978d0052d: file prog.c, line 4. main () at prog.c:4 4 return 0; Current language: auto; currently minimal (gdb) q The program is running. Exit anyway? (y or n) y Now gdb just hangs there and does nothing instead of exiting as expected. It doesn't react to ^C but one can easily kill it with ^Z and then kill %%. Here's the end of ktrace of that session (ended after a few seconds with ^Z and kill %%): 67153 gdb 1521448750.813660 GIO fd 1 wrote 47 bytes "The program is running. Exit anyway? (y or n) " 67153 gdb 1521448750.813672 RET write 47/0x2f 67153 gdb 1521448750.813678 CALL fstat(0,0x7f7ffffdc400) 67153 gdb 1521448750.813689 STRU struct stat { dev=1040, ino=78463, mode=crw--w---- , nlink=1, uid=1000<"theo">, gid=4<"tty">, rdev=1285, atime=1521448750<"Mar 19 09:39:10 2018">.807154547, mtime=1521448750<"Mar 19 09:39:10 2018">.807154547, ctime=1521448750<"Mar 19 09:39:10 2018">.807154547, size=0, blocks=0, blksize=65536, flags=0x0, gen=0x0 } 67153 gdb 1521448750.813696 RET fstat 0 67153 gdb 1521448750.813702 CALL mmap(0,0x10000,0x3<PROT_READ|PROT_WRITE>,0x1002<MAP_PRIVATE|MAP_ANON>,-1,0) 67153 gdb 1521448750.813724 RET mmap 19305116499968/0x118ed29c8000 67153 gdb 1521448750.814022 CALL fcntl(0,F_ISATTY) 67153 gdb 1521448750.814033 RET fcntl 1 67153 gdb 1521448750.814041 CALL read(0,0x118ed29c8000,0x10000) 67153 gdb 1521448752.475069 GIO fd 0 read 2 bytes "y " 67153 gdb 1521448752.475089 RET read 2 67153 gdb 1521448752.475099 CALL sigprocmask(SIG_BLOCK,0<>) 67153 gdb 1521448752.475108 RET sigprocmask 0<> 67153 gdb 1521448752.475118 CALL ptrace(PT_KILL,13232,0,0) 67153 gdb 1521448752.475130 RET ptrace 0 67153 gdb 1521448752.475137 CALL wait4(13232,0x7f7ffffdc4cc,0<>,0) 67153 gdb 1521448752.475160 RET wait4 13232/0x33b0 67153 gdb 1521448752.475164 CALL wait4(13232,0x7f7ffffdc494,0<>,0) 67153 gdb 1521448761.561842 PSIG SIGTERM SIG_DFL 13232 a.out 1521448761.561954 PSIG SIGHUP SIG_DFL