Even though he didn't plan to let the get comfortable my design, that's exactly what happened. To us it seems logical to never let your guard down, but in reality you probably would after several months of this guy not popping up again and with no sign of him ever returning. But that doesn't change the fact they should have been prepared to defend the prison from attack by anyone. They were only focusing on defending it from the Walkers.
I like how in the last 20 or so issues, I forget which. Rick says something like "we got this down, killing the dead" after killing some Walkers. The biggest problem in the world is coexisting with other people that are trying to survive too.
Sucks so bad he's gone.
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