The regular X10 brand wall switches are the least reliable of all of the X10 modules, so it doesn't surprise me that you are having a problem with a WS4777, but whether you send the command from the AH S/W or a macro shouldn't make any difference (either way the command is coming from the CM11A). What happens if you try to turn it on with a timer? Also, what happens if you unplug your CM11A and plug the transceiver in the outlet that it was plugged into and try to control it with your keyfob?
Despite this strangeness, I figure it is probably a signal related issue. Try unplugging (don't just turn off) everything that is on the same circuit as the WS4777 and see if it starts to work for you.
Let me know what happens. I will do my best to help you, but this is really a strange one.