I mean it really depends on how much trouble you’re in. If you’re in deep they’re gonna be watching every thing you do no matter what. So any kind of message that looks suspect is gonna be investigated, even stuff like “Aunt Mary” or whatever is gonna have someone trying to figure it out.

The best way to do it is to exit the monitored communication entirely, either a burner phone with coded language, or having your communications come from someone else on the inside. That’s really the only way you’ll get around it, and even that can still be caught.