Reloading an executable when it changes.

Hi everyone,
I've got a setup with gdb running on host machine, an arm board running gdbserver, and a serial line connecting the two. I'm able to remote debug over the serial line.
My goal after compiling and deploying a program (over uMTP) to the board , is to have gdbserver in conjunction with the gdb client, automatically relaunch the debug session if the executable of current program being traced just changed. For now I use the file + run combo in the client console. Is this something gdb can do? Or am I being to wishful..
Sincerely,
Brandon