GDB on Mavericks doesn't work when connecting via ssh - ssh

Question

I have a brew version of gdb installed on Mavericks. It is codesigned and I can debug without issue when connected locally:
$ gdb myprog
GNU gdb (GDB) 7.7.1
Copyright (C) 2014 Free Software Foundation, Inc.
License GPLv3+: GNU GPL version 3 or later <http://gnu.org/licenses/gpl.html>
This is free software: you are free to change and redistribute it.
There is NO WARRANTY, to the extent permitted by law. Type "show copying"
and "show warranty" for details.
This GDB was configured as "x86_64-apple-darwin13.3.0".
Type "show configuration" for configuration details.
For bug reporting instructions, please see:
<http://www.gnu.org/software/gdb/bugs/>.
Find the GDB manual and other documentation resources online at:
<http://www.gnu.org/software/gdb/documentation/>.
For help, type "help".
Type "apropos word" to search for commands related to "word"...
Reading symbols from myprog...done.
(gdb) b main
Breakpoint 1 at 0x1000028e6: file main.c, line 38.
(gdb) r
Starting program: myprog
Breakpoint 1, main (argc=1, argv=0x7fff5fbffae8) at main.c:38
38 float pi=4.*(float)atan((double)1.);
However, if I first connect to the host using ssh, gdb now no longer works:
$ ssh localhost
Last login: Tue Jul 15 11:57:44 2014 from localhost
$ gdb myprog
GNU gdb (GDB) 7.7.1
blah blah...
Reading symbols from myprog...done.
(gdb) b main
Breakpoint 1 at 0x1000028e6: file main.c, line 38.
(gdb) r
Starting program: myprog
Unable to find Mach task port for process-id 826: (os/kern) failure (0x5).
(please check gdb is codesigned - see taskgated(8))
(gdb)
Does anyone know why this happens and how to fix it?