I have to do this every so often. From times when I go and pack up a bunch of cigars for some out of town trip and then they just get stuffed back in when they don't get smoked. When I go to pack up my secret Santa I have to organize things a bit to make room..

When I do this I try to put same brands in same trays. Keep maw in together and put cigars in the trays I pulled them out of.