I'm guessing your problem is that the Wifi signal occasionally gets blocked from reaching the far oak. (Could be as simple as a person standing in the wrong place, or the microwave running etc).
By default (standard mode), Oaks are configured to so that when they lose Wifi (I think it was for 3 minutes or longer, but can't remember where I saw that length of time mentioned, so might not be true), they will drop into Config mode.
There are alternative configuration modes you can set the Oak to run in, so that if it loses Wifi, it will keep looking for the Wifi to re-appear rather than drop into Config mode. When you are uploading your code to the Oak, you can choose to upload it in "Manual mode" which will make it so that it will ignore Wifi timeouts, and hold onto the run-time code.
Once configured for manual mode, if you ever want to get the Oak into config mode, you just have to short out Pin1 to GND and it will reboot into config mode.
I'm sure there must be better instructions on how to do this somewhere, but I couldn't find them right now. Hope this makes enough sense for you to find how to use it.